40736-26-3

Usage

Uses

Used in Organic Synthesis:
N-Methanesulfonylimidazole is used as a reagent for the synthesis of various functional groups and pharmaceutical intermediates due to its versatility and mild reaction conditions.
Used in Pharmaceutical Industry:
N-Methanesulfonylimidazole is used as a key component in the synthesis of complex molecular structures for the development of new pharmaceuticals, contributing to the advancement of drug discovery and innovation.
Used in Peptide Synthesis:
In the field of peptide chemistry, N-Methanesulfonylimidazole is employed as a reagent for the synthesis of peptide derivatives, facilitating the formation of peptide bonds and enhancing the efficiency of peptide synthesis processes.
Used in Nucleoside and Heterocyclic Compound Synthesis:
N-Methanesulfonylimidazole is utilized as a reagent in the synthesis of nucleosides and heterocyclic compounds, enabling the creation of diverse and complex molecular structures with potential applications in various fields, including medicine and materials science.

InChI:InChI=1/C4H6N2O2S/c1-9(7,8)6-3-2-5-4-6/h2-4H,1H3

Upstream product

• 288-32-4 1H-imidazole 
• 124-63-0 methanesulfonyl chloride 
• 7189-69-7 N,N`-sulfuryldiimidazole 
• 333-27-7 methyl trifluoromethanesulfonate 
• 82220-41-5 tert-butylphenylphosphinic imidazolidide 
• 7143-01-3 Methanesulfonic anhydride 
• 16913-98-7 1-(Diethoxyphosphinyl)imidazole 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 67711-52-8 1-(diisopropoxyphosphinyl)imidazole 

Downstream Products

• 288-32-4 1H-imidazole 
• 75-75-2 methanesulfonic acid 
• 10040-95-6 1-(4-methoxyphenyl)-1H-imidazole 
• 10040-93-4 1-(2-methoxyphenyl)-imidazole 
• 1609033-82-0 1-((1H-imidazol-1-yl)sulfonyl)-4-phenylpiperazine 

Relevant academic research and scientific papers

Highly efficient preparation of amides from aminium carboxylates using N-(p-toluenesulfonyl) imidazole

Treatment of aminium carboxylates with N-(p-toluenesulfonyl)imidazole in the presence of triethylamine in DMF at 100 °C afforded the corresponding amides in good to excellent yields. N-(p-Toluenesulfonyl)imidazole proved to be a highly efficient coupling reagent for the preparation of numerous structurally diverse primary, secondary and tertiary amides.

3-substituted-N-(4-hydroxynaphthalen-1-yl)arylsulfonamides as a novel class of selective Mcl-1 inhibitors: Structure-based design, synthesis, SAR, and biological evaluation

Mcl-1, an antiapoptotic member of the Bcl-2 family of proteins, is a validated and attractive target for cancer therapy. Overexpression of Mcl-1 in many cancers results in disease progression and resistance to current chemotherapeutics. Utilizing high-throughput screening, compound 1 was identified as a selective Mcl-1 inhibitor and its binding to the BH3 binding groove of Mcl-1 was confirmed by several different, but complementary, biochemical and biophysical assays. Guided by structure-based drug design and supported by NMR experiments, comprehensive SAR studies were undertaken and a potent and selective inhibitor, compound 21, was designed which binds to Mcl-1 with a Ki of 180 nM. Biological characterization of 21 showed that it disrupts the interaction of endogenous Mcl-1 and biotinylated Noxa-BH3 peptide, causes cell death through a Bak/Bax-dependent mechanism, and selectively sensitizes Eμ-myc lymphomas overexpressing Mcl-1, but not Eμ-myc lymphoma cells overexpressing Bcl-2. Treatment of human leukemic cell lines with compound 21 resulted in cell death through activation of caspase-3 and induction of apoptosis.

Solvent free, highly chemoselective N and O-acylation on silica and silica magnesium oxide: A recyclable solid surface

Silica or silica/magnesium oxide mixed surface mediates the N and O-acylation, benzoylation or sulfonylation of hosts of substrates under solvent free conditions at ambient temperature with high chemoselectivity.

Alkylation, Acylation and Silylation of Azoles

Performing alkylation, acylation and silylation reactions in separate deprotonation and nucleophilic displacement steps allows for better control of reaction conditions and facilitates problem handling in these processes.In the alkylation of azoles the alkylating agents and solvents possess individual reaction capabilities which seem to be approximately additive.Monoalkylation occurs if the sum of the normalized reaction potentials is equal or larger than the pKa value of the azole.Dialkylation is avoided by keeping the sum of the normalized reaction potentials below the pKa value of the alkylazole.The applicability of these principles is demonstrated by the development of effective procedures for the methylation, benzylation, acetylation, methoxycarbonylation and trimethylsilylation of azoles.

A CONVENIENT SYNTHESIS OF PHOSPHORUS AND SULFONYL-SUBSTITUTED N-IMIDAZOLES (TRIAZOLES) USING THE CORRESPONDING ACID CHLORIDES AND N-TRIMETHYLSILYL IMIDAZOLES (TRIAZOLES)

The synthetic route phosphorus and sulfonyl-substituted N-imidazoles (triazoles) has been elaborated based on the method proposed by Birkofer et al.The appropriate compounds are obtained in high yield and of analytical purity by the action of N-trimethylsilyl imidazole (triazole) on the corresponding acid chlorides.

Phosphoric and Phosphinic Sulfonic Anhydrides - Reinvestigation and Corrections. Novel Methods of Synthesis

Earlier works from this and other laboratories on phosphoric and phosphinic sulfonic anhydrides have been reinvestigated.It was found that no single reaction described in the past provides a general method for the production of mixed anhydrides RR'P(O)SO2R'' (3) in high yields of isolated products.The following three efficient synthetic procedures leading to pure anhydrides 3 are described: a) Trifluoromethanesulfonic acid promoted reaction of phosphinic acid 9 with sulfonic triazolides 10. b) Reaction of phosphinic and phosphoric imidazolides 13 with sulfonic acid 6. c) Reaction of 13 with sulfonic anhydride 15.All methods result in high yields.Some chemical properties of the anhydrides 3 are described.