13228-41-6Relevant articles and documents
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Stephens,Castro
, p. 3313 (1963)
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Improved synthesis of indoles from 2,3-epoxypropionic acid esters [5]
Shchelkunov,Yashnova,Li,Shchelkunov
, p. 1319 - 1319 (2002)
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A Synthetic Route to Chiral Benzo-Fused N-Heterocycles via Sequential Intramolecular Hydroamination and Asymmetric Hydrogenation of Anilino-Alkynes
Xu, Cong,Feng, Yu,Li, Faju,Han, Jiahong,He, Yan-Mei,Fan, Qing-Hua
, p. 3979 - 3990 (2019/11/14)
An efficient sequential intramolecular hydroamination/asymmetric hydrogenation reaction under catalysis of a single chiral ruthenium complex or a binary system consisting of achiral gold complex and chiral ruthenium complex has been reported. A diverse range of enantioenriched benzo-fused N-heterocycles, including 1,2,3,4-tetrahydroquinoline, indoline, and 2,3,4,5-tetrahydro-1H-benzo[b]azepine derivatives, were obtained from anilino-alkynes in high yields (up to 98%) with moderate to excellent enantioselectivities (up to 98% ee) under mild conditions. This protocol features good functional group tolerance and high atom economy. Furthermore, this catalytic protocol is applicable to gram-scale synthesis of a naturally occurring alkaloid, (-)-Angustureine.
New telmisartan-derived PPARγ agonists: Impact of the 3D-binding mode on the pharmacological profile
Obermoser, Victoria,Urban, Margarethe E.,Murgueitio, Manuela S.,Wolber, Gerhard,Kintscher, Ulrich,Gust, Ronald
, p. 138 - 152 (2016/08/30)
In previous studies, the 4′-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid was identified as pharmacophoric core for PPARγ activation. In this structure-activity relationship study the C2-alkyl chain was elongated and the 2-COOH group was changed to a carbamide/carbonitrile or shifted to the 3- or 4-position. Furthermore, the benzo[d]imidazole was exchanged by 2,3-dihydrobenzo[d]thiazole or 1H-indole. C2-propyl derivatives showed the profile of partial agonists, while elongation of the C2-chain to that of an n-heptyl group or a 4-COOH shift changed the pharmacological profile to that of a potent full agonist. This finding can be explained by binding to the LBD in different ligand conformations. Two anchoring points (Tyr473 and Arg288) exist in the LBD, which have to be contacted to achieve receptor activation. In a crystal violet chemosensitivity assay using COS-7?cells and LNCaP cells expressing PPARγ only the carbamide derivatives influenced the cell growth, independently on the presence of the PPARγ. Therefore, receptor mediated cytotoxicity can be excluded.
