Page last updated: 2024-12-06
1-(trimethylsilyl)-1h-imidazole
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
1-(trimethylsilyl)-1H-imidazole is a versatile reagent in organic synthesis. It is commonly used as a silylating agent, protecting group, and catalyst. The compound is synthesized through the reaction of imidazole with trimethylsilyl chloride in the presence of a base, such as triethylamine. 1-(trimethylsilyl)-1H-imidazole is often employed to introduce trimethylsilyl groups onto various functional groups, such as alcohols, amines, and carboxylic acids. This silylation process can enhance the reactivity or stability of the molecule. The compound's ability to form stable silyl enol ethers makes it a valuable reagent in aldol condensation reactions. 1-(trimethylsilyl)-1H-imidazole has also been investigated as a catalyst in a range of organic transformations, including ring-opening metathesis and Diels-Alder reactions. Its unique properties and reactivity make it a subject of ongoing research in various fields, including medicinal chemistry, materials science, and synthetic organic chemistry.'
N-trimethylsilylimidazole : A member of the class of imidazoles in which the hydrogen at position 1 is replaced by a trimethylsilyl group. N-trimethylsilylimidazole is a derivatisation agent used in gas chromatography/mass spectrometry applications. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 28925 |
| CHEMBL ID | 1565732 |
| CHEBI ID | 85063 |
| SCHEMBL ID | 217284 |
| MeSH ID | M0152797 |
Synonyms (68)
| Synonym |
|---|
| LS-13172 |
| 1-(trimethylsilyl)imidazole |
| nsc139860 |
| imidazole, 1-(trimethylsilyl)- |
| (trimethylsilyl)imidazole |
| n-(trimethylsilyl)imidazole , |
| 18156-74-6 |
| 1-(trimethylsilyl)-1h-imidazole |
| n-(trimethylsilyl)imidazol |
| tsim |
| nsc-139860 |
| 1h-imidazole, 1-(trimethylsilyl)- |
| brn 0606148 |
| einecs 242-040-3 |
| ai3-52901 |
| imidazole, n-(trimethylsilyl)- |
| nsc 139860 |
| n-(trimethylsilyl)-imidazole |
| bdbm7945 |
| imidazole n-1 deriv. 6 |
| MLS001074885 |
| smr000568407 |
| 1-(trimethylsilyl)imidazole, 96% |
| n-trimethylsilylimidazole |
| T0693 |
| T0585 |
| imidazol-1-yl(trimethyl)silane |
| NCGC00246980-01 |
| 1-trimethylsilylimidazole |
| unii-px8k4r8kwx |
| ec 242-040-3 |
| 5-23-04-00456 (beilstein handbook reference) |
| px8k4r8kwx , |
| n-trimethylsilylimidizole |
| A812623 |
| 1-imidazolyl(trimethyl)silane |
| AKOS005216567 |
| HMS2231B11 |
| FT-0629329 |
| BP-21124 |
| SCHEMBL217284 |
| 1-trimethylsilanyl-1h-imidazole |
| n-trimethylsilyl-imidazol |
| 1-(trimethylsilyl)-imidazole |
| imidazol-1-yl-trimethyl-silane |
| trimethylsilylimidazole |
| DTXSID5066326 |
| CHEMBL1565732 |
| chebi:85063 , |
| 1-(trimethylsily)imidazole |
| 1-imidazolyltrimethylsilane |
| imidazole, tms derivative |
| trimethylimidazosilane |
| ct3600 |
| mfcd00005280 |
| J-802246 |
| n-(trmethylslyl)mdazole |
| J-523191 |
| 1-(trimethylsilyl)imidazole, >=98.0% |
| 1-(trimethylsilyl)imidazole, for gc derivatization |
| AT19146 |
| BCP18905 |
| Q27158312 |
| n-trimethylsilyl imidazole |
| n-trimethylsilylimidazole [trimethylsilylating reagent] |
| tms-imidazole (=n-trimethylsilylimidazole) [for gas chromatography] |
| EN300-247308 |
| CS-0158137 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Roles (1)
| Role | Description |
|---|---|
| chromatographic reagent | A reagent used to improve selectivity in chromatographic analyses or separations, e.g. by formation of a derivative or by modification of the mobile phase. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
Drug Classes (2)
| Class | Description |
|---|---|
| imidazoles | A five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton. |
| N-silyl compound | Any organosilicon compound that contains at least one silicon-nitrogen bond. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
Protein Targets (6)
Potency Measurements
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Beta-lactamase | Escherichia coli K-12 | Potency | 10.0000 | 0.0447 | 17.8581 | 100.0000 | AID485294 |
| Chain A, Putative fructose-1,6-bisphosphate aldolase | Giardia intestinalis | Potency | 22.3872 | 0.1409 | 11.1940 | 39.8107 | AID2451 |
| thioredoxin reductase | Rattus norvegicus (Norway rat) | Potency | 100.0000 | 0.1000 | 20.8793 | 79.4328 | AID588453 |
| chromobox protein homolog 1 | Homo sapiens (human) | Potency | 100.0000 | 0.0060 | 26.1688 | 89.1251 | AID540317 |
| geminin | Homo sapiens (human) | Potency | 0.1852 | 0.0046 | 11.3741 | 33.4983 | AID624296; AID624297 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Glutaminyl-peptide cyclotransferase | Homo sapiens (human) | Ki | 167.0000 | 0.2620 | 2.9358 | 7.0000 | AID1796109 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (2)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| peptidyl-pyroglutamic acid biosynthetic process, using glutaminyl-peptide cyclotransferase | Glutaminyl-peptide cyclotransferase | Homo sapiens (human) |
| protein modification process | Glutaminyl-peptide cyclotransferase | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Molecular Functions (3)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| protein binding | Glutaminyl-peptide cyclotransferase | Homo sapiens (human) |
| zinc ion binding | Glutaminyl-peptide cyclotransferase | Homo sapiens (human) |
| glutaminyl-peptide cyclotransferase activity | Glutaminyl-peptide cyclotransferase | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Ceullar Components (5)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| extracellular region | Glutaminyl-peptide cyclotransferase | Homo sapiens (human) |
| specific granule lumen | Glutaminyl-peptide cyclotransferase | Homo sapiens (human) |
| extracellular exosome | Glutaminyl-peptide cyclotransferase | Homo sapiens (human) |
| tertiary granule lumen | Glutaminyl-peptide cyclotransferase | Homo sapiens (human) |
| ficolin-1-rich granule lumen | Glutaminyl-peptide cyclotransferase | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Bioassays (14)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID1796109 | QC Inhibition Testing from Article 10.1074/jbc.M309077200: \\Identification of human glutaminyl cyclase as a metalloenzyme. Potent inhibition by imidazole derivatives and heterocyclic chelators.\\ | 2003 | The Journal of biological chemistry, Dec-12, Volume: 278, Issue:50 | Identification of human glutaminyl cyclase as a metalloenzyme. Potent inhibition by imidazole derivatives and heterocyclic chelators. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (13)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 3 (23.08) | 18.7374 |
| 1990's | 1 (7.69) | 18.2507 |
| 2000's | 2 (15.38) | 29.6817 |
| 2010's | 5 (38.46) | 24.3611 |
| 2020's | 2 (15.38) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 12.26
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.
| This Compound (12.26) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 14 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||