18952-41-5

Usage

Uses

Used in Chemical Synthesis:
Methanethioamide, N-methylis used as an intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable building block for the development of new chemical entities.
Used in Pharmaceutical Industry:
Methanethioamide, N-methylis used as a key component in the production of pharmaceuticals. Its presence in the synthesis process contributes to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
Methanethioamide, N-methylis also utilized in the agrochemical sector, where it plays a crucial role in the synthesis of various agrochemicals. Its incorporation in the production process helps in the development of effective crop protection agents and other agricultural products.

Upstream product

• 74-90-8 hydrogen cyanide 
• 74-89-5 methylamine 
• 123-39-7 N-Methylformamide 
• 556-61-6 methyl thioisocyanate 
• 78-94-4 methyl vinyl ketone 
• 3446-89-7 4-(Methylthio)benzaldehyde 
• 42445-46-5 2-bromo-1-(4-methylsulfanyl-phenyl)-ethanone 
• 197905-69-4 2-[2-(4-methylsulfanylphenyl)-2-oxoethyl]-3-oxobutanic acid methyl ester 

Downstream Products

• 123-39-7 N-Methylformamide 
• 77827-61-3 Zn⁽²⁺⁾*2Cl^(1-)*2HCSNHCH₃=ZnCl₂(HCSNHCH₃)2 
• 6610-29-3 4-methylthiosemicarbazide 
• 99380-74-2 ((1S,2S,6R,7R)-8-Methyl-3,5,9-trioxo-4-oxa-10-thia-8-aza-tricyclo[5.2.1.0^2,6]dec-1-yl)-acetic acid 

Relevant academic research and scientific papers

Novel reduction of isothiocyanates to thioformamides with SmI2 and tert-butyl alcohol in the presence of HMPA

Isocyanates react with SmI2 and tert-butyl alcohol in the presence of HMPA to give thioformamides in excellent yields under mild conditions.

A fluorescent target-guided Paal-Knorr reaction

It has become increasingly apparent that high-diversity chemical reactions play a significant role in the discovery of bioactive small molecules. Here, we describe an expanse of this paradigm, combining a ‘target-guided synthesis’ concept with Paal-Knorr chemistry applied to the preparation of fluorescent ligands for human prostaglandin-endoperoxide synthase (COX-2).

Evaluation of thioamides, thiolactams and thioureas as hydrogen sulfide (H2S)donors for lowering blood pressure

Hydrogen sulfide (H2S)is a biologically important gaseous molecule that exhibits promising protective effects against a variety of pathological processes. For example, it was recognized as a blood pressure lowering agent. Aligned with the need for easily modifiable platforms for the H2S supply, we report here the preparation and the H2S release kinetics from a series of structurally diversified thioamides, thiolactams and thioureas. Three different thionation methods based on the usage of a phosphorus pentasulfide and Lawesson reagent were applied to prepare the target thioamides and thiolactams. Furthermore, obtained H2S donors were evaluated both in in vivo and in vitro studies. The kinetic parameters of the liberating H2S was determined and compared with NaHS and GYY4137 using two different detection technics i.e.; fluorescence labeling 7-azido-4-methyl-2H-chromen-2-one and 5,5‘-dithiobis (2-nitrobenzoic acid), sulfhydryl probe, also known as the Ellman's reagent. We have proved that the amount of releasing H2S from these compounds is controllable through structural modifications. Finally, the present study shows a hypotensive response to an intravenous administration of the developed donors in the anesthetized rats.

AN IMPROVED PROCESS FOR THE PREPARATION OF PYRROLE DERIVATIVES

The present invention relates to an improved process for the preparation of pyrroles derivatives having hypolipidemic and hypocholesteremic activities. In particular, the invention relates to an improved process for the preparation of 2- ethoxy-3-(4-(2-(2-methyl-5-(4-(methylthio)phenyl)-1H-pyrrol-1-yl)ethoxy) phenyl)propanoate and its pharmaceutically acceptable salts, hydrates, solvates, polymorphs or intermediates thereof. The invention also relates to an improved process for the preparation of mesylate compound (A1).

A PROCESS FOR PREPARATION OF PYRROLES HAVING HYPOLIPIDEMIC HYPOCHOLESTEREMIC ACTIVITIES

The present invention provides pyrroles having hypolipidemic hypocholesteremic activities. The invention provides saroglitazar and its pharmaceutically acceptable salts, hydrates, solvates, polymorphs or intermediates thereof. The invention also provides a process for the preparation of saroglitazar. The invention further provides intermediates as well process for preparation thereof.

A class of pyrrole derivatives endowed with analgesic/anti-inflammatory activity

We report the synthesis and bio-pharmacological evaluation of a class of pyrrole derivatives featuring a small appendage fragment (carbaldehyde, oxime, nitrile) on the central core. Compound 1c proved to be extremely effective in vivo, showing an interesting anti-nociceptic profile that is comparable to reference compounds already marketed, hence representing a great stimulus for a further improvement of this class of molecules.

Improving the solubility of a new class of antiinflammatory pharmacodynamic hybrids, that release nitric oxide and inhibit cycloxygenase-2 isoenzyme

The development of a novel class of pharmacodynamic hybrids that inhibits COX-2 isoform is reported. These molecules display enhanced nitric oxide releasing properties due to the presence of an ionisable moiety. The in vivo analgesic/anti-inflammatory activity was maintained in relation to the parent compounds.

Novel analgesic/anti-inflammatory agents: Diarylpyrrole acetic esters endowed with nitric oxide releasing properties

The design of compounds that are able to inhibit cyclooxygenase (COX) and to release nitric oxide (NO) should give rise to drugs endowed with an overall safer profile for the gastrointestinal and cardiovascular systems. Herein we report a new class of pyrrole-derived nitrooxy esters (11a-j), cyclooxygenase-2 (COX-2) selective inhibitors endowed with NO releasing properties, with the goal of generating new molecules able to both strongly inhibit this isoform and reduce the related adverse side effects. Taking into account the metabolic conversion of nitrooxy esters into corresponding alcohols, we also studied derivatives 12a-j. All compounds proved to be very potent and selective COX-2 inhibitors; nitrooxy derivatives displayed interesting ex vivo NO-dependent vasorelaxing properties. Compounds 11c, 11d, 12c, and 12d were selected for further in vivo studies that highlited good anti-inflammatory and antinociceptive activities. Finally, two selected compounds (11c and 12c) tested in human whole blood (HWB) assay proved to be preferential inhibitors of COX-2.

Identification of a novel pyrrole derivative endowed with antimycobacterial activity and protection index comparable to that of the current antitubercular drugs streptomycin and rifampin

A hit optimization procedure based on isosteric and bioisosteric replacement of decorating groups at both the N1 and the C5 phenyl rings of 1,5-diarylpyrroles led to identification of 4-((1-(4-fluorophenyl)-2-methyl-5- (4-(methylthio)phenyl)-1H-pyrrol-3-yl)methyl)thiomorpholine that is characterized by a very high activity toward both Mycobacterium tuberculosis 103471 and H37Rv strains (MIC values of 0.125 μg/mL), and a safe profile in terms of cytotoxicity (CC50 of >128 μg/mL) and protection index (>1000). Antitubercular activity and protection index of the new compound are comparable to those found for the current antitubercular drugs streptomycin and rifampin.

Novel Ester and acid derivatives of the 1,5-diarylpyrrole Scaffold as anti-inflammatory and analgesic agents. Synthesis and in vitro and in vivo biological evaluation

A new generation of selective cyclooxygenase-2 (COX-2) inhibitors (coxibs) was developed to circumvent the major side effects of cyclooxygenase-1 (COX-1) and COX-2 inhibitors (stomach ulceration and nephrotoxicity). As a consequence, coxibs are extremely valuable in treating acute and chronic inflammatory conditions. However, the use of coxibs, such as rofecoxib (Vioxx), was discontinued because of the high risk of cardiovascular adverse events. More recent clinical findings highlighted how the cardiovascular toxicity of coxibs could be mitigated by an appropriate COX-1 versus COX-2 selectivity. We previously reported a set of substituted 1,5-diarylpyrrole derivatives, selective for COX-2. Here, we describe the synthesis of new1,5-diarylpyrroles along with their inhibitory effects in vitro, ex vivo, and in vivo toward COX isoenzymes and their analgesic activity. Isopropyl-2-methyl-5-[4- (methylsulfonyl)phenyl]-1-phenyl-1H-pyrrole-3-acetate (10a), a representative member of the series, was selected for pharmacokinetic and metabolic studies. 2009 American Chemical Society.