1010833-04-1Relevant articles and documents
Allylic thiocyanates as a new class of antitubercular agents
Silveira, Gustavo P.,Ferreira, Misael,Fernandes, Luciano,Moraski, Garrett C.,Cho, Sanghyun,Hwang, Changhwa,Franzblau, Scott G.,Sa, Marcus M.
supporting information, p. 6486 - 6489 (2012/10/29)
TB is a global public health emergency in which new drugs are desperately needed. Herein we report on the synthesis of a diverse panel of 41 aryl allylic azides, thiocyanates, isothiouronium salts, and N,N′-diacetylisothioureas that were evaluated for their in vitro activity against replicating and non-replicating Mycobacterium tuberculosis (Mtb) H37Rv and toxicity to VERO cells. We found a selective group of new and promising compounds having good (micromolar) to excellent (sub-micromolar) potency against replicating Mtb H37Rv. Allylic thiocyanates bearing halophenyl (halo = 2-Br, 4-Br, 4-Cl, 4-F), 4-methylphenyl and 2-naphthyl moieties were the most active as antitubercular agents. In particular, the 2-bromophenyl-substituted thiocyanate showed MIC = 0.25 μM against replicating Mtb, MIC = 8.0 μM against non-replicating Mtb and IC50 = 32 μM in the VERO cellular toxicity assay.
Synthesis of allylic thiocyanates and novel 1,3-thiazin-4-ones from 2-(bromomethyl)alkenoates and S-nucleophiles in aqueous medium
Sá, Marcus M.,Fernandes, Luciano,Ferreira, Misael,Bortoluzzi, Adailton J.
, p. 1228 - 1232 (2008/09/17)
Allylic thiocyanates and novel heterocycles containing the 1,3-thiazin-4-one core are easily obtained in high yields and mild conditions by nucleophilic displacement of 2-(bromomethyl)alkenoates (derived from Morita-Baylis-Hillman adducts) with sulphur-ce
