- Visible Light-Driven C-3 Functionalization of Indoles over Conjugated Microporous Polymers
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Metal-free and heterogeneous organic photocatalysts provide an environmentally friendly alternative to traditional metal-based catalysts. This paper reports a series of carbazole-based conjugated microporous polymers (CMPs) with tunable redox potentials and explores their photocatalytic performance with regard to C-3 formylation and thiocyanation of indoles. Conjugated polymers were synthesized through FeCl3 mediated Friedel-Crafts reactions, and their redox potentials were well regulated by simply altering the nature of the core (i.e., 1,4-dibenzyl, 1,3,5-tribenzyl, or 1,3,5-triazin-2,4,6-triyl). The resulting CMPs exhibited high surface areas, visible light absorptions, and tunable semiconductor-range band gaps. With the highest oxidative capability, CMP-CSU6 derived from 1,3,5-tri(9H-carbazol-9-yl)benzene showed the highest efficiency for C-3 formylation and thiocyanation of indoles at room temperature. Notably, the as-made catalysts can be easily recovered with good retention of photocatalytic activity and reused at least five times, suggesting good recyclability. These results are significant for constructing high-performance porous polymer catalysts with tunable photoredox potentials targeting an efficient material design for catalysis.
- Zhang, Weijie,Tang, Juntao,Yu, Wenguang,Huang, Qiao,Fu, Yu,Kuang, Guichao,Pan, Chunyue,Yu, Guipeng
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p. 8084 - 8091
(2018/07/30)
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- Aerobic transition-metal-free visible-light photoredox indole C-3 formylation reaction
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An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs molecular oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups.
- Li, Xiang,Gu, Xiangyong,Li, Yongjuan,Li, Pixu
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p. 1897 - 1900
(2014/06/24)
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- Towards total synthesis of communesins and perophoramidine: Unexpected cascade reaction of Michael-Mannich-Mannich additions
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A new type of chiral amidinobenzodiene 5 was prepared from isatin in ten steps. While attempting to prepare the core structure from 5 and tryptamine derivative 17 via a hetero Diels-Alder reaction for the total synthesis of communesin and perophoramidine, we observed an unexpected three-step, one-pot cascade reaction of Michael-Manich-Manich additions. The cascade reaction between 5 and 17 yielded diasteromers 21a and 21b with a complex polycyclic skeleton of 2,3,4,5-diindolinohexahydropyrrole in 76% yield and a ratio of 3:1. The stereochemistry of 21a was confirmed by X-ray crystal-structural analysis. Georg Thieme Verlag Stuttgart · New York.
- Wu, Haoxing,Xiao, Xue,Qin, Yong
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scheme or table
p. 907 - 910
(2011/06/17)
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- Pyrazolone-based anaplastic lymphoma kinase (ALK) inhibitors: Control of selectivity by a benzyloxy group
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Anaplastic lymphoma kinase (ALK) is transmembrane receptor tyrosine kinase, with oncogenic variants that have been implicated in ALCL, NSCLC and other cancers. Screening of a VEGFR2-biased kinase library resulted in identification of 1 which showed cross-reactivity with ALK. SAR on the indole segment of 1 showed that a subtle structural modification (the ethoxy group of 1 changed to a benzyloxy to generate 5a) enhanced potency (ALK), selectivity for VEGFR2 and IR along with improvement in metabolic stability. From docking studies of ALK versus VEGFR2 kinase, we postulated that the loss of entropy of the VEGFR2 in the bound form with 5a might be the origin of the reduced activity against that protein. Modification of the heterocyclic segment showed that thiazole-bearing pyrazolones preserved enzyme potency, and enhanced inhibition of NPM-ALK autophosphorylation in ALK-positive ALCL cells (Karpas-299). SAR of the benzyloxy group resulted in compounds which demonstrated good cellular potency in Karpas-299 cells. Compound 8 showed best overall profile for the series with broad kinome selectivity and liver micorsome stability. Compound 8 showed reasonable iv PK in rat, but with little oral exposure.
- Tripathy, Rabindranath,McHugh, Robert J.,Ghose, Arup K.,Ott, Gregory R.,Angeles, Thelma S.,Albom, Mark S.,Huang, Zeck,Aimone, Lisa D.,Cheng, Mangeng,Dorsey, Bruce D.
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scheme or table
p. 7261 - 7264
(2012/02/13)
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- PYRAZOLOPYRIDINE DERIVATIVES AS INHIBITORS OF BETA-ADRENERGIC RECEPTOR KINASE 1
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The invention relates to 6-amido substituted pyrazolopyridine derivatives of the formula (I) useful as inhibitors of beta-adrenergic receptor kinase 1 (βARK-1 ), compositions containing such-compounds and their use for the treatment and prevention of chro
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Page/Page column 24
(2008/06/13)
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- Heteroaryl-O-glucosides as novel sodium glucose co-transporter 2 inhibitors. Part 1
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A series of benzo-fused heteroaryl-O-glucosides was synthesized and evaluated in SGLT1 and 2 cell-based functional assays. Indole-O-glucoside 10a and benzimidazole-O-glucoside 18 exhibited potent in vitro SGLT2 inhibitory activity.
- Zhang, Xiaoyan,Urbanski, Maud,Patel, Mona,Zeck, Roxanne E.,Cox, Geoffrey G.,Bian, Haiyan,Conway, Bruce R.,Beavers, Mary Pat,Rybczynski, Philip J.,Demarest, Keith T.
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p. 5202 - 5206
(2007/10/03)
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