1964-45-0Relevant academic research and scientific papers
Enantioselective hydroarylation or hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes
Hu, Fangdong,Jia, Jie,Li, Ximing,Xia, Ying
, p. 896 - 901 (2021/02/01)
An efficient protocol for the asymmetric hydroarylation and hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes has been developed. The combination of a rhodium(I) precatalyst and a chiral diene ligand constitutes the catalytic system, which enables the facile synthesis of 2,3-dihydrobenzo[b]thiophene 1,1-dioxides in good yields with high enantioselectivities. The merging of this asymmetric hydroarylation with the downstream alkylations delivers 2,3-dihydrobenzo[b]thiophene 1,1-dioxides that contain two continuous quaternary stereocenters with high enantioselectivities in a diastereodivergent manner.
NEW COMPOUNDS
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Page/Page column 51, (2012/04/04)
A compound of formula (I), wherein A is S, O or a double bond, and L is a substituted thiazolyl, phenyl or pyridyl. The compound is useful for the treatment of inflammation and cancer.
Preparation and pharmacological evaluation of a novel series of 2-(phenylthio)benzo[b]thiophenes as selective MT2 receptor ligands
Mésangeau, Christophe,Fraise, Mika?l,Delagrange, Philippe,Caignard, Daniel Henri,Boutin, Jean Albert,Berthelot, Pascal,Yous, Sa?d
scheme or table, p. 1835 - 1840 (2011/05/06)
A series of N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl) ethyl)acylamides was synthesized and evaluated for binding affinity and intrinsic activity at melatonin receptors. The affinity of each compound for the melatonin receptors was determined by binding studies on cloned human MT 1 and MT2 receptors expressed in CHO cells. Agonist and antagonist potency was measured on the [35S]GTPγS binding assay for the most interesting compounds. The new derivatives 8-14 showed modest to high selectivity (between 4 and 220) for MT2 receptors. The most selective compound, N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl) ethyl)but-3-enamide (14), an MT2 ligand with affinity for the MT 2 receptor similar to that of melatonin and a 220-fold preference over MT1 receptors, acts as a partial agonist. In addition, N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl)ethyl)propionamide (9), a nanomolar MT2 ligand with a good selectivity ratio (MT 1/MT2 = 51) shows antagonist activity on both melatonin receptors.
Convenient synthesis of 3-substituted benzo[b]thiophenes by iodine-mediated cyclization of α-substituted 2-(1-Phenylethylthio)styrenes
Kobayashi, Kazuhiro,Nakamura, Daizo,Miyamoto, Kazuna,Morikawa, Osamu,Konishi, Hisatoshi
experimental part, p. 1780 - 1784 (2009/07/25)
A new and convenient method for the preparation of 3-substituted benzo[b]thiophenes was developed. α-Substituted 2-(1-phenylethylthio) styrenes, which could easily be prepared from 2-mercaptophenyl ketones or benzenethiols in two or three steps, respectively, underwent 5-endo cyclization on treatment with iodine in the presence of sodium hydrogencarbonate in acetonitrile at room temperature to give 3-substituted benzo[b]thiophenes in fair to good yields.
Synthesis of Substituted Benzothiophenes by Acid-Catalyzed Cyclization of Thiophenylacetals and Ketones
Ple, Patrick A.,Marnett, Lawrence J.
, p. 1271 - 1272 (2007/10/02)
Benzothiophenes substituted at the 3 position with methyl or carboxymethyl and at the 5 position with methyl, methoxy, chloro, bromo and nitro were prepared by cyclization of thiophenyl-acetals and ketones using a suspension of polyphosphoric acid in refluxing chlorobenzene.The overall efficiency of this method is superior to literature procedures because of the lower temperature and the limited amount of PPA used.
