Diversity-oriented functionalization of indolizines at the C3 position via multicomponent Kabachnik-Fields reaction

被引：11
作者：
Kim, Jinwoo
Heo, Yunkyung
Jung, Youngeun
Lee, Jinu [1 ]
Kim, Ikyon [1 ]
机构：
[1] Yonsei Univ, Coll Pharm, 85 Songdogwahak Ro, Incheon 21983, South Korea
来源：
TETRAHEDRON | 2017年 / 73卷 / 39期
基金：
新加坡国家研究基金会;
关键词：
Multicomponent reaction; Aminophosphonates; Indolizine; Diversity-oriented synthesis; Gap junction inhibition; JUNCTIONAL INTERCELLULAR COMMUNICATION; ONE-POT SYNTHESIS; ALPHA-AMINOPHOSPHONATES; AMINO-ACIDS; EFFICIENT; PHOSPHONATES; COMPLEXITY; INHIBITORS; BIOLOGY; ROUTE;
D O I：
10.1016/j.tet.2017.08.017
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A diversity-oriented approach to new indolizines highly functionalized at the C3 position was achieved by using the Kabachnik-Fields three-component reaction. Some of the synthesized compounds exhibited a significant gap junction inhibitory activity. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5759 / 5768
页数：10
相关论文
共 36 条
[21]   A new high-throughput screening-compatible gap junctional intercellular communication assay [J].
Lee, Ju Yeon ;
Choi, Eun Ju ;
Lee, Jinu .
BMC BIOTECHNOLOGY, 2015, 15
[22]   Terbinafine inhibits gap junctional intercellular communication [J].
Lee, Ju Yeun ;
Yoon, Sei Mee ;
Choi, Eun Ju ;
Lee, Jinu .
TOXICOLOGY AND APPLIED PHARMACOLOGY, 2016, 307 :102-107
[23]   Propylphosphonic anhydride (T3P®) mediated one-pot three-component synthesis of racemic dialkyl (2-substituted-3-oxo-2,3-dihydro-1H-isoindol-1-yl)phosphonates [J].
Milen, Matyas ;
Dancso, Andras ;
Foldesi, Tamas ;
Slegel, Peter ;
Volk, Balazs .
TETRAHEDRON, 2016, 72 (33) :5091-5099
[24]   Synthesis, characterization and biological evaluation of anti-cancer indolizine derivatives via inhibiting β-catenin activity and activating p53 [J].
Moon, Seong-Hee ;
Jung, Youngeun ;
Kim, Seong Hwan ;
Kim, Ikyon .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (01) :110-113
[25]   Construction of benzo-fused indolizines, pyrrolo[1,2-a]quinolines via alkyne-carbonyl metathesis [J].
Nayak, Maloy ;
Kim, Ikyon .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (37) :9697-9708
[26]   A novel Cu(OTf)2 mediated three component high yield synthesis of α-aminophosphonates [J].
Paraskar, Abhimanyu S. ;
Sudalai, Arumugam .
ARKIVOC, 2006, :183-189
[27]   When Indolizine Meets Quinoline: Diversity-Oriented Synthesis of New Polyheterocycles and Their Optical Properties [J].
Park, Sujin ;
Kwon, Dah In ;
Lee, Jeeyeon ;
Kim, Ikyon .
ACS COMBINATORIAL SCIENCE, 2015, 17 (08) :459-469
[28]   Electron-withdrawing group effect in aryl group of allyl bromides for the successful synthesis of indolizines via a novel [3+3] annulation approach [J].
Park, Sujin ;
Kim, Ikyon .
TETRAHEDRON, 2015, 71 (13) :1982-1991
[29]   Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity [J].
Ruijter, Eelco ;
Scheffelaar, Rachel ;
Orru, Romano V. A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6234-6246
[30]   HIGHLY EFFICIENT ONE-POT SYNTHESIS OF α-AMINOPHOSPHONATES CATALYZED BY YTTERBIUM TRIFLATE IN WATER [J].
Shen, MingGui ;
Shang, ShiBin ;
Song, ZhanQian ;
Wang, Dan ;
Rao, XiaoPing ;
Gao, Hong ;
Wang, Juan .
SYNTHETIC COMMUNICATIONS, 2014, 44 (03) :361-367
1234