41828-16-4

Upstream product

• 51861-05-3 S-Methyl N-cyclohexyl(thiocarbamate) 
• 106-48-9 4-chloro-phenol 
• 3712-40-1 tert-butyl cyclohexylcarbamate 
• 3173-53-3 Cyclohexyl isocyanate 

Relevant academic research and scientific papers

Phenolic N-monosubstituted carbamates: Antitubercular and toxicity evaluation of multi-targeting compounds

The research of novel antimycobacterial drugs represents a cutting-edge topic. Thirty phenolic N-monosubstituted carbamates, derivatives of salicylanilides and 4-chlorophenol, were investigated against Mycobacterium tuberculosis H37Ra, H37Rv including multidrug- and extensively drug-resistant strains, Mycobacterium avium, Mycobacterium kansasii, Mycobacterium aurum and Mycobacterium smegmatis as representatives of nontuberculous mycobacteria (NTM) and for their cytotoxic and cytostatic properties in HepG2 cells. Since salicylanilides are multi-targeting compounds, we determined also inhibition of mycobacterial isocitrate lyase, an enzyme involved in the maintenance of persistent tuberculous infection. The minimum inhibitory concentrations were from ≤0.5 μM for both drug-susceptible and resistant M. tuberculosis and from ≤0.79 μM for NTM with no cross-resistance to established drugs. The presence of halogenated salicylanilide scaffold results into an improved activity. We have verified that isocitrate lyase is not a key target, presented carbamates showed only moderate inhibitory activity (up to 18% at a concentration of 10 μM). Most of the compounds showed no cytotoxicity for HepG2 cells and some of them were without cytostatic activity. Cytotoxicity-based selectivity indexes of several carbamates for M. tuberculosis, including resistant strains, were higher than 125, thus favouring some derivatives as promising features for future development.

Investigation of salicylanilide and 4-chlorophenol-based N-monosubstituted carbamates as potential inhibitors of acetyl- and butyrylcholinesterase

Based on the presence of carbamate moiety, twenty salicylanilide N-monosubstituted carbamates concomitantly with their parent salicylanilides and five newly prepared 4-chlorophenyl carbamates obtained from isocyanates were investigated using Ellman's method for their in vitro inhibitory activity against acetylcholinesterase (AChE) from electric eel and butyrylcholinesterase (BChE) from equine serum. The carbamates and salicylanilides exhibited mostly a moderate inhibition of both cholinesterase enzymes with IC50 values ranging from 5 to 235 μM. IC50 values for AChE were in a narrower concentration range when compared to BChE, but many of the compounds produced a balanced inhibition of both cholinesterases. The derivatives were comparable or superior to rivastigmine for AChE inhibition, but only a few of carbamates also for BChE. Several structure-activity relationships were identified, e.g., N-phenethylcarbamates produce clearly favourable BChE inhibition. The compounds also share convenient physicochemical properties for CNS penetration.

One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines

A highly efficient one-pot procedure for the synthesis of carbamates and thiocarbamates has been described. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, the isocyanate intermediates were generated in situ for further reactions with alcohols and thiols to afford the desired carbamates and thiocarbamates in high yields.

An easy and efficient one-step procedure for the preparation of alkyl and aryl alkylcarbamates from S-methyl N-alkylthiocarbamates

A general, one-step procedure for the synthesis of alkyl and aryl alkylcarbamates, by the direct reaction of S-methyl N-alkylthiocarbamates with alcohols or phenols in toluene at reflux in the presence of triethylamine, is reported. All the target products were obtained in high yield (15 examples, average yield 94%) and very high purity (>99.2%). The recovery of a co-product of industrial interest, methanethiol, in an amount of one mole for each mole of thiocarbamate, with complete exploitation of the reagent, should also be noted. Georg Thieme Verlag Stuttgart.

One-pot, three-step preparation of alkyl and aryl alkylcarbamates from S-methyl N-alkylthiocarbamates

A general procedure for the synthesis of alkyl and aryl alkylcarbamates starting from the corresponding 5-methyl N-alkylthiocarbamates is described. This procedure consists of three steps that are carried out in a one-pot fashion, without isolating the intermediate N-alkylcarbamoyl chlorides or alkyl isocyanates. All the target products were obtained in high yields (16 examples, average yield 91%). To be noted is the recovery of a co-product of industrial interest, dimethyl disulfide, in a half mole amount for each mole of thiocarbamate, with complete exploitation of the reagent. The alkyl isocyanates, if required, can also be isolated in high yields. Georg Thieme Verlag Stuttgart.