Compounds > 1-(2',5'-bis-o-(tert-butyldimethylsilylribofuranosyl)-3-n-methylthymine)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)
Page last updated: 2024-12-06

1-(2',5'-bis-o-(tert-butyldimethylsilylribofuranosyl)-3-n-methylthymine)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

You've described a rather complex molecule with a long and specific name! Here's a breakdown of its components and its potential relevance to research:

**Breaking down the name:**

* **1-(2',5'-bis-o-(tert-butyldimethylsilylribofuranosyl)-3-n-methylthymine):** This is the core nucleoside structure. Let's dissect it:
* **Thymine:** A pyrimidine base found in DNA.
* **3-n-methylthymine:** A modified thymine base with a methyl group added at the 3rd nitrogen position.
* **Ribofuranosyl:** A sugar molecule (ribose) in its cyclic form.
* **2',5'-bis-o-(tert-butyldimethylsilyl):** This indicates two protecting groups (tert-butyldimethylsilyl) attached to the 2' and 5' positions of the ribose sugar. Protecting groups are commonly used in organic chemistry to temporarily block reactive sites of a molecule, allowing other reactions to occur without affecting these sites.
* **3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide):** This indicates a specific connection to the core nucleoside:
* **3'-spiro-5'':** This means the structure is connected to the 3' position of the sugar with a spiro linkage, forming a new ring.
* **4''-amino-1'',2''-oxathiole-2'',2''-dioxide:** This describes a five-membered heterocyclic ring with a sulfur atom and an amino group attached to the 4 position. This ring is connected to the spiro carbon and contains a sulfone group (SO2).

**Potential Importance for Research:**

This molecule, likely a synthetic analog of a natural nucleoside, could have several potential uses in research:

* **Nucleic Acid Modifications:** The complex structure suggests it could be part of a larger molecule, possibly an oligonucleotide or a DNA/RNA analog. Researchers may be investigating how this modification affects the structure, stability, or function of nucleic acids.
* **Drug Discovery:** The inclusion of a sulfone group and an amino group could make this molecule a potential lead compound for drug development. These functional groups often contribute to pharmacological activity.
* **Biophysical Studies:** Researchers may be interested in understanding how the structure impacts the biophysical properties of the molecule, such as its binding affinity to other molecules or its fluorescence characteristics.

**Additional Information Needed:**

To fully understand the importance of this molecule, we would need more context. The research goals, the specific application, and the potential target molecules are all critical factors.

**In conclusion,** the molecule you described likely has significant relevance to research in the fields of medicinal chemistry, bioorganic chemistry, or nucleic acid chemistry.

1-(2',5'-bis-O-(tert-butyldimethylsilylribofuranosyl)-3-N-methylthymine)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide): structure given in first source; specific against HIV-1 replication [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65007
CHEMBL ID211582
MeSH IDM0219785

Synonyms (11)

Synonym
tsao-m3t
142102-79-2
bdbm50192289
1-[(5r,6r,8r,9r)-4-amino-9-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dioxo-1,7-dioxa-2lambda*6*-thia-spiro[4.4]non-3-en-8-yl]-3,5-dimethyl-1h-pyrimidine-2,4-dione
CHEMBL211582 ,
2,4(1h,3h)-pyrimidinedione, 1-((5r,6r,8r,9r)-4-amino-9-(((1,1-dimethylethyl)dimetylsilyl)oxy)-6-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)-1,7-dioxa-2-thiaspiro(4.4)non-3-en-8-yl)-3,5-dimethyl-
1-(2',5'-bis-o-(tert-butyldimethylsilylribofuranosyl)-3-n-methylthymine)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)
2,4(1h,3h)-pyrimidinedione, 1-(4-amino-9-(((1,1-dimethylethyl)dimetylsilyl)oxy)-6-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)-1,7-dioxa-2-thiaspiro(4.4)non-3-en-8-yl)-3,5-dimethyl-, s,s-dioxide, (5r-(5alpha,6beta,8beta,9alpha))-
DTXSID10931351
1-[4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dioxo-1,7-dioxa-2lambda~6~-thiaspiro[4.4]non-3-en-8-yl]-3,5-dimethylpyrimidine-2,4(1h,3h)-dione
1-((5r,6r,8r,9r)-4-amino-9-((tert-butyldimethylsilyl)oxy)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl)-3,5-dimethylpyrimidine-2,4(1h,3h)-dione

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" If UC42 was combined with the [2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5"-(4"-amino-1",2"- oxathiole-2",2"-dioxide)]-beta-D-pentofuranosyl (TSAO) derivative of N3-methylthymine (TSAO-m3T), virus breakthrough could be prevented for a much longer time, and at much lower concentrations, than if the compounds were used individually."( Suppression of the breakthrough of human immunodeficiency virus type 1 (HIV-1) in cell culture by thiocarboxanilide derivatives when used individually or in combination with other HIV-1-specific inhibitors (i.e., TSAO derivatives).
Balzarini, J; Camarasa, MJ; De Clercq, E; Karlsson, A; Pérez-Pérez, MJ; San-Félix, A; Vélazquez, S, 1995)		0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)22.50000.00011.076810.0000AID199100; AID199101; AID268623; AID268624; AID593599
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1EC50 (µMol)0.05000.00040.61539.7000AID81407; AID81408
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (66)

Assay IDTitleYearJournalArticle
AID593594Antiviral activity against HIV1 3B harboring reverse transcriptase Y181C mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID104580Inhibitory activity against HIV-1 in MT-4 cell culture.2001Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12
Identification of a putative binding site for [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase.
AID593597Antiviral activity against HIV1 3B harboring reverse transcriptase Y188L mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID45828Inhibitory activity against HIV-2 in CEM cell culture.2001Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12
Identification of a putative binding site for [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase.
AID593608Ratio of EC50 for HIV1 3B harboring reverse transcriptase N136A/Q/K mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593603Antiviral activity against wild type HIV1 infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593510Antiviral activity against HIV1 3B harboring reverse transcriptase V179N mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID81407Effective concentration required to inhibit HIV-1 induced cytopathicity in CEM cell culture by 50%.2002Journal of medicinal chemistry, Aug-29, Volume: 45, Issue:18
Synthesis of 3' '-substituted TSAO derivatives with anti-HIV-1 and anti-HIV-2 activity through an efficient palladium-catalyzed cross-coupling approach.
AID593503Antiviral activity against HIV1 3B harboring reverse transcriptase L100I mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593598Antiviral activity against HIV1 3B harboring reverse transcriptase G190E mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593509Antiviral activity against HIV1 3B harboring reverse transcriptase E138D mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID106967Concentration required to inhibit HIV-1 induced cytopathicity in MT-4 cells by 50%1992Journal of medicinal chemistry, Aug-07, Volume: 35, Issue:16
TSAO analogues. Stereospecific synthesis and anti-HIV-1 activity of 1-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro -5''- (4''-amino-1'',2''-oxathiole 2'',2''-dioxide) pyrimidine and pyrimidine-modified nucleosides.
AID593599Inhibition of wild type HIV-1 reverse transcriptase-mediated polymerization reaction after 30 mins2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593505Antiviral activity against HIV1 3B harboring reverse transcriptase K103N mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID198230Inhibitory activity against wild-type HIV-1 reverse transcriptase2001Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12
Identification of a putative binding site for [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase.
AID268626Inhibition of MT4 cell viability2006Journal of medicinal chemistry, Aug-10, Volume: 49, Issue:16
Structure-activity relationships of [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5' '-(4' '-amino-1' ',2' '-oxathiole-2' ',2' '-dioxide)thymine derivatives as inhibitors of HIV-1 reverse transcriptase dimerization.
AID246162Effective concentration required to inhibit HIV-2 ROD in CEM cell culture2005Journal of medicinal chemistry, Feb-24, Volume: 48, Issue:4
Novel [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2" -dioxide) derivatives with anti-HIV-1 and anti-human-cytomegalovirus activity.
AID593699Ratio of EC50 for HIV1 3B harboring reverse transcriptase Y188H mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593610Ratio of EC50 for HIV1 3B harboring reverse transcriptase E138D mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID619907Cytotoxicity against human HuH7 cells after 72 hrs2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Synthesis and in vitro activity of novel N-3 acylated TSAO-T compounds against HIV-1 and HCV.
AID619908Antiviral activity against HIV1 harboring reverse transcriptase E138K mutant infected in human CEM cells assessed as inhibition of virus-induced cytopathicity after 4 days2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Synthesis and in vitro activity of novel N-3 acylated TSAO-T compounds against HIV-1 and HCV.
AID593506Antiviral activity against HIV1 3B harboring reverse transcriptase V106A mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID268623Inhibition of FLAG-p66/HIS-p51-mediated HIV1 reverse transcriptase dimerization2006Journal of medicinal chemistry, Aug-10, Volume: 49, Issue:16
Structure-activity relationships of [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5' '-(4' '-amino-1' ',2' '-oxathiole-2' ',2' '-dioxide)thymine derivatives as inhibitors of HIV-1 reverse transcriptase dimerization.
AID198070Inhibitory activity against E138K mutant reverse transcriptase2001Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12
Identification of a putative binding site for [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase.
AID199100Inhibitory concentration against wild type HIV-1 reverse transcriptase (RT) using poly rC.dG as the template or primer2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Hybrids of [TSAO-T]-[foscarnet]: The first conjugate of foscarnet with a non-nucleoside reverse transcriptase inhibitor through a labile covalent ester bond.
AID619905Cytotoxicity against human CEM cells after 4 days2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Synthesis and in vitro activity of novel N-3 acylated TSAO-T compounds against HIV-1 and HCV.
AID232779Selectivity index was defined as the ratio of CC50 to EC501992Journal of medicinal chemistry, Aug-07, Volume: 35, Issue:16
TSAO analogues. Stereospecific synthesis and anti-HIV-1 activity of 1-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro -5''- (4''-amino-1'',2''-oxathiole 2'',2''-dioxide) pyrimidine and pyrimidine-modified nucleosides.
AID246176Effective concentration required to inhibit HIV-1 IIIB in MT-4 cell culture2005Journal of medicinal chemistry, Feb-24, Volume: 48, Issue:4
Novel [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2" -dioxide) derivatives with anti-HIV-1 and anti-human-cytomegalovirus activity.
AID593606Ratio of EC50 for HIV1 3B harboring reverse transcriptase K103N mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID246168Effective concentration required to inhibit HIV-1 IIIB in CEM cell culture2005Journal of medicinal chemistry, Feb-24, Volume: 48, Issue:4
Novel [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2" -dioxide) derivatives with anti-HIV-1 and anti-human-cytomegalovirus activity.
AID593602Inhibition of HIV-1 reverse transcriptase K1001E and E138K mutant-mediated polymerization reaction after 30 mins2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID268624Inhibition of HIV1 reverse transcriptase RNA-dependent DNA polymerase activity2006Journal of medicinal chemistry, Aug-10, Volume: 49, Issue:16
Structure-activity relationships of [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5' '-(4' '-amino-1' ',2' '-oxathiole-2' ',2' '-dioxide)thymine derivatives as inhibitors of HIV-1 reverse transcriptase dimerization.
AID245934Cytostatic concentration required to inhibit MT-4 cell proliferation2005Journal of medicinal chemistry, Feb-24, Volume: 48, Issue:4
Novel [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2" -dioxide) derivatives with anti-HIV-1 and anti-human-cytomegalovirus activity.
AID322455Antiviral activity against HIV2 ROD in CEM cells assessed as inhibition of viral replication2008Bioorganic & medicinal chemistry letters, Apr-01, Volume: 18, Issue:7
Synthesis, anti-HIV-1 activity, and modeling studies of N-3 Boc TSAO compound.
AID593612Ratio of EC50 for HIV1 3B harboring reverse transcriptase Y181C mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593601Inhibition of HIV-1 reverse transcriptase E138K mutant-mediated polymerization reaction after 30 mins2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593605Ratio of EC50 for HIV1 3B harboring reverse transcriptase L100I mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID106604Cytotoxic concentration required to inhibit MT-4 cell proliferation by 50%2002Journal of medicinal chemistry, Aug-29, Volume: 45, Issue:18
Synthesis of 3' '-substituted TSAO derivatives with anti-HIV-1 and anti-HIV-2 activity through an efficient palladium-catalyzed cross-coupling approach.
AID593595Antiviral activity against HIV1 3B harboring reverse transcriptase Y181I mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID199101Inhibitory concentration against wild type HIV-1/138Lys reverse transcriptase (RT) using [3H]dGTP as a radioligand2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Hybrids of [TSAO-T]-[foscarnet]: The first conjugate of foscarnet with a non-nucleoside reverse transcriptase inhibitor through a labile covalent ester bond.
AID106600Cytotoxic concentration required to reduce MT-4 cell viability by 50%1992Journal of medicinal chemistry, Aug-07, Volume: 35, Issue:16
TSAO analogues. Stereospecific synthesis and anti-HIV-1 activity of 1-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro -5''- (4''-amino-1'',2''-oxathiole 2'',2''-dioxide) pyrimidine and pyrimidine-modified nucleosides.
AID246169Effective concentration required to inhibit HIV-2 ROD in MT-4 cell culture2005Journal of medicinal chemistry, Feb-24, Volume: 48, Issue:4
Novel [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2" -dioxide) derivatives with anti-HIV-1 and anti-human-cytomegalovirus activity.
AID198106Inhibitory activity against R172A mutant reverse transcriptase2001Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12
Identification of a putative binding site for [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase.
AID45827Inhibitory activity against HIV-1 in CEM cell culture.2001Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12
Identification of a putative binding site for [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase.
AID83114Effective concentration required to inhibit HIV-2 induced cytopathicity in MT-4 cell culture by 50%.2002Journal of medicinal chemistry, Aug-29, Volume: 45, Issue:18
Synthesis of 3' '-substituted TSAO derivatives with anti-HIV-1 and anti-HIV-2 activity through an efficient palladium-catalyzed cross-coupling approach.
AID593702Ratio of IC50 for HIV-1 reverse transcriptase K1001E and E138K mutant to IC50 for HIV-1 wild type reverse transcriptase2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593596Antiviral activity against HIV1 3B harboring reverse transcriptase Y188H mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID83113Effective concentration required to inhibit HIV-2 induced cytopathicity in CEM cell culture by 50%.2002Journal of medicinal chemistry, Aug-29, Volume: 45, Issue:18
Synthesis of 3' '-substituted TSAO derivatives with anti-HIV-1 and anti-HIV-2 activity through an efficient palladium-catalyzed cross-coupling approach.
AID268625Antiviral activity against HIV1 in MT4 cells2006Journal of medicinal chemistry, Aug-10, Volume: 49, Issue:16
Structure-activity relationships of [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5' '-(4' '-amino-1' ',2' '-oxathiole-2' ',2' '-dioxide)thymine derivatives as inhibitors of HIV-1 reverse transcriptase dimerization.
AID619903Antiviral activity against HIV1 3B infected in human CEM cells assessed as inhibition of virus-induced cytopathicity after 4 days2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Synthesis and in vitro activity of novel N-3 acylated TSAO-T compounds against HIV-1 and HCV.
AID593607Ratio of EC50 for HIV1 3B harboring reverse transcriptase V106A mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID322454Antiviral activity against HIV1 3B in CEM cells assessed as inhibition of viral replication2008Bioorganic & medicinal chemistry letters, Apr-01, Volume: 18, Issue:7
Synthesis, anti-HIV-1 activity, and modeling studies of N-3 Boc TSAO compound.
AID593611Ratio of EC50 for HIV1 3B harboring reverse transcriptase V179N mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593609Ratio of EC50 for HIV1 3B harboring reverse transcriptase E138K mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593508Antiviral activity against HIV1 3B harboring reverse transcriptase E138K mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593700Ratio of EC50 for HIV1 3B harboring reverse transcriptase Y188L mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID104581Inhibitory activity against HIV-2 in MT-4 cell culture.2001Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12
Identification of a putative binding site for [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase.
AID81408Effective concentration required to inhibit HIV-1 induced cytopathicity in MT-4 cell culture by 50%.2002Journal of medicinal chemistry, Aug-29, Volume: 45, Issue:18
Synthesis of 3' '-substituted TSAO derivatives with anti-HIV-1 and anti-HIV-2 activity through an efficient palladium-catalyzed cross-coupling approach.
AID593698Ratio of EC50 for HIV1 3B harboring reverse transcriptase Y181I mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593600Inhibition of HIV-1 reverse transcriptase K101E mutant-mediated polymerization reaction after 30 mins2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID619906Antiviral activity against HCV2a JFH1 infected in human Huh7 cells assessed as inhibition of viral replication after 72 hrs by luciferase reporter gene assay2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Synthesis and in vitro activity of novel N-3 acylated TSAO-T compounds against HIV-1 and HCV.
AID619904Antiviral activity against HIV2 ROD infected in human CEM cells assessed as inhibition of virus-induced cytopathicity after 4 days2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Synthesis and in vitro activity of novel N-3 acylated TSAO-T compounds against HIV-1 and HCV.
AID593504Antiviral activity against wild type HIV1 3B infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593604Antiviral activity against wild type HIV2 infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593507Antiviral activity against HIV1 3B harboring reverse transcriptase N136A/Q/K mutant infected in human CEM cells assessed as inhibition of syncytia formation2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
AID593701Ratio of EC50 for HIV1 3B harboring reverse transcriptase G190E mutant to EC50 for wild type HIV1 3B2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Crystal structure of tert-butyldimethylsilyl-spiroaminooxathioledioxide-thymine (TSAO-T) in complex with HIV-1 reverse transcriptase (RT) redefines the elastic limits of the non-nucleoside inhibitor-binding pocket.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's6 (33.33)18.2507
2000's10 (55.56)29.6817
2010's2 (11.11)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.26

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.26 (24.57)
Research Supply Index3.09 (2.92)
Research Growth Index4.35 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.76%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (95.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
nsc 615985
NSC 615985: structure given in first source; potent inhibitor of HIV reproduction		1.9810
foscarnet
Foscarnet: An antiviral agent used in the treatment of cytomegalovirus retinitis. Foscarnet also shows activity against human herpesviruses and HIV.. phosphonoformic acid : Phosphoric acid in which one of the hydroxy groups is replaced by a carboxylic acid group. It is used as the trisodium salt as an antiviral agent in the treatment of cytomegalovirus retinitis (CMV retinitis, an inflamation of the retina that can lead to blindness) and as an alternative to ganciclovir for AIDS patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity.		2.0210carboxylic acid;
one-carbon compound;
phosphonic acids		antiviral drug;
geroprotector;
HIV-1 reverse transcriptase inhibitor;
sodium-dependent Pi-transporter inhibitor
nevirapine
Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.		1.9810cyclopropanes;
dipyridodiazepine		antiviral drug;
HIV-1 reverse transcriptase inhibitor
delavirdine
Delavirdine: A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1.. delavirdine : The amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection.		2.420aminopyridine;
indolecarboxamide;
N-acylpiperazine;
sulfonamide		antiviral drug;
HIV-1 reverse transcriptase inhibitor
thymidine
[no description available]		4.790pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		210alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
aspartic acid
Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.		210aspartate family amino acid;
aspartic acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
mouse metabolite;
neurotransmitter
glutamine
Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.		210amino acid zwitterion;
glutamine family amino acid;
glutamine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
Escherichia coli metabolite;
human metabolite;
metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
lysine
Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.		210aspartate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
lysine;
organic molecular entity;
proteinogenic amino acid		algal metabolite;
anticonvulsant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
uridine
[no description available]		4.250uridinesdrug metabolite;
fundamental metabolite;
human metabolite
tyrosine
Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.		210amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		210amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
carboxin
Carboxin: A systemic agricultural fungicide and seed treatment agent.. carboxin : An anilide obtained by formal condensation of the amino group of aniline with the carboxy group of 2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid. A fungicide for control of bunts and smuts that is normally used as a seed treatment.		1.9810anilide fungicide;
anilide;
enamide;
organosulfur heterocyclic compound;
oxacycle;
secondary carboxamide		antifungal agrochemical;
EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		210glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
efavirenz
efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.		210acetylenic compound;
benzoxazine;
cyclopropanes;
organochlorine compound;
organofluorine compound		antiviral drug;
HIV-1 reverse transcriptase inhibitor
thymidine 5'-triphosphate
thymidine 5'-triphosphate: RN given refers to parent cpd. dTTP : A thymidine phosphate having a triphosphate group at the 5'-position.		210pyrimidine 2'-deoxyribonucleoside 5'-triphosphate;
thymidine phosphate		Escherichia coli metabolite;
mouse metabolite
tsao-t
[no description available]		4.7290
methylthymidine
methylthymidine: RN given refers to N-3-methylthymidine		1.9810
2'-deoxycytidine 5'-triphosphate
2'-deoxycytidine 5'-triphosphate: RN given refers to unlabeled parent cpd		2102'-deoxycytidine phosphate;
pyrimidine 2'-deoxyribonucleoside 5'-triphosphate		Escherichia coli metabolite;
human metabolite;
mouse metabolite
2'-c-methylcytidine
2'-C-methylcytidine: structure in first source		2.0610
r 82150
R 82150: structure given in first source; inhibits HIV-1 replication		2.3920
r-82913
R-82913: antiviral target on reverse transcriptase of HIV-1		1.9810
uc-781
[no description available]		210
2',3'-dideoxyguanosine 5'-triphosphate
[no description available]		2.420
ConditionIndicatedRelationship StrengthStudiesTrials
Cytomegalovirus
A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.		02.0210
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted
[description not available]		02.0610
HIV Coinfection
[description not available]		02.4320
Hepatitis C
INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.		02.0610
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		02.4320