22857-79-0Relevant academic research and scientific papers
Substituted Benzothietes: Synthesis and a Quantum Chemical Investigation of Their Cycloreversion Properties
Ahlburg, Nils L.,Velarde, Andres R.,Kieber-Emmons, Matthew T.,Jones, Peter G.,Werz, Daniel B.
supporting information, p. 4255 - 4260 (2020/06/04)
A flexible synthesis for highly substituted benzothietes that does not require flash-vacuum pyrolysis was developed. This allows for the use of a number of functional groups and nonvaporizable molecules. Highly stabilized derivatives were isolated. The molecular orbital properties of various benzothietes were evaluated by density functional methods. The mechanism of the cycloreversion of the four-membered ring was compared to that of the oxygen-containing analogues.
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.
