14786-83-5Relevant academic research and scientific papers
Divergent Synthesis of Disulfanes and Benzenesulfonothioates Bearing 2-Aminofurans From N-Tosylhydrazone-Bearing Thiocarbamates
Mai, Shaoyu,Song, Qiuling
supporting information, p. 7952 - 7957 (2017/06/27)
An efficient and convenient synthesis of valuable disulfanes and benzenesulfonothioates, having a 2-aminofuran framework, has been developed by employing a copper-catalyzed transformation of readily available N-tosylhydrazone-bearing thiocarbamates. This method features an inexpensive metal catalyst, mild reaction conditions, good functional-group tolerance, short reaction times, and delivers valuable and complex products. A copper carbene generated from an N-tosylhydrazone-bearing thiocarbamate is proposed as the key intermediate for the transformation and it triggers the subsequent cascade. Remarkably, the Ts anion released from N-tosylhydrazone further serves as a nucleophile, thus rendering the formation of benzenesulfonothioates under controlled conditions.
Palladium-catalyzed intramolecular oxidative C-H sulfuration of aryl thiocarbamates
Zhao, Yingwei,Xie, Yinjun,Xia, Chungu,Huang, Hanmin
supporting information, p. 2471 - 2476 (2014/09/17)
A palladium-catalyzed intramolecular C-H bond sulfuration reaction of aryl thiocarbamates has been developed. This strategy provides a new route to benzo[d][1,3]oxathiol-2-ones with tolerance of a wide range of substituents. Mechanistic studies suggested
Substituted 2-(3′,4′,5′-trimethoxybenzoyl)-benzo[b] thiophene derivatives as potent tubulin polymerization inhibitors
Romagnoli, Romeo,Baraldi, Pier Giovanni,Carrion, Maria Dora,Cruz-Lopez, Olga,Tolomeo, Manlio,Grimaudo, Stefania,Cristina, Antonietta Di,Pipitone, Maria Rosaria,Balzarini, Jan,Brancale, Andrea,Hamel, Ernest
experimental part, p. 5114 - 5122 (2010/09/14)
The central role of microtubules in cell division and mitosis makes them a particularly important target for anticancer agents. On our early publication, we found that a series of 2-(3′,4′,5′-trimethoxybenzoyl)-3- aminobenzo[b]thiophenes exhibited strong antiproliferative activity in the submicromolar range and significantly arrested cells in the G2-M phase of the cell cycle and induced apoptosis. In order to investigate the importance of the amino group at the 3-position of the benzo[b]thiophene skeleton, the corresponding 3-unsubstituted and methyl derivatives were prepared. A novel series of inhibitors of tubulin polymerization, based on the 2-(3,4,5-trimethoxybenzoyl)-benzo[b]thiophene molecular skeleton with a methoxy substituent at the C-4, C-5, C-6 or C-7 position on the benzene ring, was evaluated for antiproliferative activity against a panel of five cancer cell lines, for inhibition of tubulin polymerization and for cell cycle effects. Replacing the methyl group at the C-3 position resulted in increased activity compared with the corresponding 3-unsubstituted counterpart. The structure-activity relationship established that the best activities were obtained with the methoxy group placed at the C-4, C-6 or C-7 position. Most of these compounds exhibited good growth inhibition activity and arrest K562 cells in the G2-M phase via microtubule depolymerization.
Novel Cyclization of S-(o-Acetylaryl) Dimethylthiocarbamates. A New Synthesis of 3-Hydroxybenzothiophenes and 2-Hydroxythiochromones
Lau, C.K.,Belanger, Patrice C.,Dufresne, C.,Scheigetz, J.
, p. 1670 - 1673 (2007/10/02)
The rearrangement of O-(o-acetylaryl) dimethylthiocarbamates to their corresponding S-aryl dimethylthiocarbamates, previously reported to be a very low yielding reaction, have been achieved in acceptable yields.The versatility of these intermediates is demonstrated by their transformation into different heterocyclic systems.Thus, when the resulting S-(acetylaryl) dimethylthiocarbamates are treated with base in the presence of air, they cyclize in a novel fashio to yield substituted N,N-dimethyl-3-hydroxybenzothiophene-2-carboxamides and substituted 2-hydroxythiochromones.In the absence of air, only the latter was formed.
