Facile and diastereoselective synthesis of 3,2′-spiropyrrolidine-oxindoles derivatives, their molecular docking and antiproliferative activities

被引：77

作者：

Kathirvelan, D. ^{[1
]}

Haribabu, J. ^{[1
]}

Reddy, B. S. R. ^{[1
]}

Balachandran, C. ^{[2
]}

Duraipandiyan, V. ^{[2
]}

机构：

[1] CSIR, Cent Leather Res Inst, Ind Chem Lab, Madras 600020, Tamil Nadu, India

[2] Loyola Coll, Entomol Res Inst, Div Microbiol & Canc Biol, Madras 600034, Tamil Nadu, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2015年 / 25卷 / 02期

关键词：

Multicomponent reaction; Spirooxindole; Pyrazole moiety; Antimicrobial activity; Molecular docking; ENANTIOSELECTIVE SYNTHESIS; MULTICOMPONENT REACTION; DISCOVERY; SPIROOXINDOLES; POTENT; ISORHYNCHOPHYLLINE; RHYNCHOPHYLLINE; INHIBITORS; ALKALOIDS; LIBRARY;

D O I：

10.1016/j.bmcl.2014.10.099

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In the present study, a series of novel highly functionalized spiropyrrolidine-oxindoles have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide formed from isatin and various amino acids such as sarcosine, proline and thioproline with the dipolarophile (E)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-(1H-indole-3-carbonyl) acrylonitrile under optimized conditions. All the synthesized compounds were evaluated for their antimicrobial activity and shown significant activity. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：389 / 399

页数：11

共 60 条

[31] A Unique Approach to the Concise Synthesis of Highly Optically Active Spirooxazolines and the Discovery of a More Potent Oxindole-Type Phytoalexin Analogue [J].

Jiang, Xianxing ;

Cao, Yiming ;

Wang, Yiqing ;

Liu, Luping ;

Shen, Fangfang ;

Wang, Rui .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15328-15333

[32]

Kamisaki H, 2011, ANGEW CHEM INT EDIT, V123, P7983

[33] Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action [J].

Kang, TH ;

Murakami, Y ;

Takayama, H ;

Kitajima, M ;

Aimi, N ;

Watanabe, H ;

Matsumoto, K .

LIFE SCIENCES, 2004, 76 (03) :331-343

[34] Rhynchophylline and isorhynchophylline inhibit NMDA receptors expressed in Xenopus oocytes [J].

Kang, TH ;

Murakami, Y ;

Matsumoto, K ;

Takayama, H ;

Kitajima, M ;

Aimi, N ;

Watanabe, H .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2002, 455 (01) :27-34

[35] 6 '-(1,3-Diphenyl-1H-pyrazol-4-yl)-7 '(1H-indol-3-ylcarbonyl)-2-oxo-1-(prop-2-en-1-yl)-5 ',6 ',7 '',7a '-tetrahydro-1'H-spiro[indoline-3,5 '-pyrrolo[1,2-c][1,3]thiazole]-7 '-carbonitrile [J].

Kannan, Piskala Subburaman ;

Kathirvelan, Devaraj ;

Reddy, Boreddy Siva Rami ;

Govindan, Elumalai ;

SubbiahPandi, Arunachalathevar .

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 :O857-+

[36] Synthesis, antibacterial activity evaluation and QSAR studies of novel dispiropyrrolidines [J].

Karthikeyan, K. ;

Sivakumar, P. M. ;

Doble, M. ;

Perumal, P. T. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (08) :3446-3452

[37] Notoamides A-D:: Prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp. [J].

Kato, Hikaru ;

Yoshida, Takushi ;

Tokue, Takanori ;

Nojiri, Yuka ;

Hirota, Hiroshi ;

Ohta, Tomihisa ;

Williams, Robert M. ;

Tsukamoto, Sachiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (13) :2254-2256

[38] Novel three-component domino reactions of ketones, isatin and amino acids: Synthesis and discovery of antimycobacterial activity of highly functionalised novel dispiropyrrolidines [J].

Kumar, Raju Suresh ;

Rajesh, Stephen Michael ;

Perumal, Subbu ;

Banerjee, Debjani ;

Yogeeswari, Perumal ;

Sriram, Dharmarajan .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (01) :411-422

[39] An expedient approach for the synthesis of dispiropyrrolidine bisoxindoles, spiropyrrolidine oxindoles and spiroindane-1,3-diones through 1,3-dipolar cycloaddition reactions [J].

Lakshmi, Neelakandan Vidhya ;

Thirumurugan, Prakasam ;

Perumal, Paramasivan T. .

TETRAHEDRON LETTERS, 2010, 51 (07) :1064-1068

[40] Formosanin C-induced apoptosis requires activation of caspase-2 and change of mitochondrial membrane potential [J].

Lee, Jenq-Chang ;

Su, Chun-Li ;

Chen, Lin-Lin ;

Won, Shen-Jeu .

CANCER SCIENCE, 2009, 100 (03) :503-513

← 1 2 3 4 5 6 →