88149-87-5Relevant academic research and scientific papers
Redox-Divergent Construction of (Dihydro)thiophenes with DMSO
Chen, Qing-An,He, Gu-Cheng,Hu, Yan-Cheng,Ji, Ding-Wei,Liu, Heng,Zhang, Xiang-Xin,Zhao, Chao-Yang
, p. 24284 - 24291 (2021/10/08)
Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.
Studies on anti-inflammatory agents. VI. Synthesis and pharmacological properties of 2,3-diarylthiophenes
Tsuji, Kiyoshi,Nakamura, Katsuya,Ogino, Takashi,Konishi, Nobukiyo,Tojo, Takashi,Ochi, Takehiro,Seki, Nobuo,Matsuo, Masaaki
, p. 279 - 286 (2007/10/03)
A series of novel 5-substituted-2,3-diarylthiophenes has been synthesized and found to be active in the rat adjuvant arthritis (AA) model and/or in the yeast-induced hyperalgesia (Randall-Selitto) assay. Among the compounds synthesized herein, 2-(4-fluorophenyl)-3-[4- (methylsulfonyl)phenyl]-S-(trifluoromethyl)thiophene (6a) exhibited the most potent activities on AA, collagen-Induced arthritis (CIA) and the delayed- type hypersensitivity response to type II collagen. 5-Bromo-2-[4- (methylamino)phenyl]-3-[4-(methylsulfinyl)phenyl]thiophene (38) is also a potent inhibitor of AA, CIA, hyperalgesia and in vitro tumor necrosis factor- α production.
Chemistry and pharmacokinetics of diarylthiophenes and terphenyls as selective COX-2 inhibitors
Pinto, Donald J.P.,Copeland, Robert A.,Covington, Maryanne B.,Pitts, William J.,Batt, Douglas G.,Orwat, Michael J.,Lam, Gilbert N.,Joshi, Amita,Chan, Yuk-Charn,Wang, Shuaige,Trzaskos, James M.,Magolda, Ronald L.,Kornhauser, David M.
, p. 2907 - 2912 (2007/10/03)
DuP697, 2-bromo-4-(4'-sulfonylmethyl)phenyl-5-(4'-fluoro)phenylthiophene, is a selective type 2 cyclooxygenase (COX-2) inhibitor. Its relatively weak COX-2 selectivity coupled with a poor human pharmacokinetic profile led us to seek improvements on the in vitro selectivity while at the same time, addressing some of its pharmacokinetic liabilities. In this paper we discuss some strategies at solving the PK issue within a class of COX-2 inhibitors. The result of these efforts led to the discovery of a new class of COX-2 inhibitors the terphenyls, which prove to be superior alternatives to the diarylthiophenes.
2,3-diaryl-5-bromothiophene compounds of use for the treatment of inflammaton and dysmenorrhea
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, (2008/06/13)
A small group of 2,3-diaryl-5-bromothiophene compounds such as 5-bromo-2-(4-methylthiophenyl)-3-(4-fluorophenyl)thiophene have been found to possess significant and unexpected antiinflammatory activity, and inhibition of prostaglandin synthetase useful fo
