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: 2024-09-23

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

Description

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

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]

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]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
nevirapine[no description available]medium10cyclopropanes;
dipyridodiazepine		antiviral drug;
HIV-1 reverse transcriptase inhibitor
r 82150[no description available]medium20
delavirdine[no description available]medium20aminopyridine;
indolecarboxamide;
N-acylpiperazine;
sulfonamide		antiviral drug;
HIV-1 reverse transcriptase inhibitor
efavirenz[no description available]medium10acetylenic compound;
benzoxazine;
cyclopropanes;
organochlorine compound;
organofluorine compound		antiviral drug;
HIV-1 reverse transcriptase inhibitor
uc-781[no description available]medium10
foscarnet[no description available]medium10carboxylic acid;
one-carbon compound;
phosphonic acids		antiviral drug;
geroprotector;
HIV-1 reverse transcriptase inhibitor;
sodium-dependent Pi-transporter inhibitor
tsao-t[no description available]medium100
2'-c-methylcytidine[no description available]medium10
thymidine[no description available]medium120pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
uridine[no description available]medium60uridinesdrug metabolite;
fundamental metabolite;
human metabolite
r-82913[no description available]medium10
carboxin[no description available]medium10anilide fungicide;
anilide;
enamide;
organosulfur heterocyclic compound;
oxacycle;
secondary carboxamide		antifungal agrochemical;
EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor
nsc 615985[no description available]medium10
methylthymidine[no description available]medium10
2',3'-dideoxyguanosine 5'-triphosphate[no description available]medium20
aspartic acid[no description available]medium10aspartate family amino acid;
aspartic acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
mouse metabolite;
neurotransmitter
lysine[no description available]medium10aspartate 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
tyrosine[no description available]medium10amino 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
alanine[no description available]medium10alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
phenylalanine[no description available]medium10amino 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
glutamine[no description available]medium10amino 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
glutamic acid[no description available]medium10glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
2'-deoxycytidine 5'-triphosphate[no description available]medium102'-deoxycytidine phosphate;
pyrimidine 2'-deoxyribonucleoside 5'-triphosphate		Escherichia coli metabolite;
human metabolite;
mouse metabolite
thymidine 5'-triphosphate[no description available]medium10pyrimidine 2'-deoxyribonucleoside 5'-triphosphate;
thymidine phosphate		Escherichia coli metabolite;
mouse metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Cytomegalovirus0low10
Hepatitis C0low10
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted0low10
HIV Coinfection0low20
HIV Infections0low20
HTLV-III Infections0low20
HTLV-III-LAV Infections0low20
Parenterally-Transmitted Non-A, Non-B Hepatitis0low10
PT-NANBH0low10
T-Lymphotropic Virus Type III Infections, Human0low20

Research Highlights

Pharmacokinetics (1)

ArticleYear
Metabolism and pharmacokinetics of the anti-HIV-1-specific inhibitor [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3-N- methyl-thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dio xide).
Biochemical pharmacology, Jul-06, Volume: 46, Issue: 1		1993
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (1)

ArticleYear
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).
Proceedings of the National Academy of Sciences of the United States of America, Jun-06, Volume: 92, Issue: 12		1995
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]