Practical synthesis, anticonvulsant, and antimicrobial activity of N-allyl and N-propargyl di(indolyl)indolin-2-ones

被引：90

作者：

Praveen, Chandrasekaran ^{[1
]}

Ayyanar, Asairajan ^{[2
]}

Perumal, Paramasivan Thirumalai ^{[1
]}

机构：

[1] Cent Leather Res Inst, Div Organ Chem, Madras 600020, Tamil Nadu, India

[2] Arulmigu Kalasalingam Coll Pharm, Dept Pharmaceut Chem, Krishnankoil 626190, Tamil Nadu, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 13期

关键词：

Copper(II) triflate; N-Allyl(propargyl)-di(indolyl)indolin-2-ones; Anticonvulsant; Antimicrobial; IN-VITRO EVALUATION; REGIOSELECTIVE SYNTHESIS; FACILE SYNTHESIS; COPPER; CYCLOADDITIONS; CONDENSATION; ISATINS; ROUTE; ACID;

D O I：

10.1016/j.bmcl.2011.04.117

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An operation friendly protocol for the synthesis of novel di(indolyl)indolin-2-ones via Cu(OTf)(2) catalyzed bis-addition of N-allyl and N-propargyl indole with isatin was developed. This methodology allowed us to achieve the products in excellent yields without requiring purification technique like column chromatography. All the synthesized compounds were evaluated for their in vivo anticonvulsant activity against maximal electroshock test. Six compounds showed maximum activity compared to the standard drug phenytoin. The scope of the new molecules as antimicrobial agents were tested against two bacterial strains (Staphylococcus aureus and Escherichia coli) and one fungal strain (Candida albicans). (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4072 / 4077

页数：6

共 51 条

[1] Domino addition/annulation of δ-alkynylaldehydes and oxygen nucleophiles:: a new entry to [1,4]oxazino[4,3-a]indoles
Abbiati, G
Canevari, V
Caimi, S
Rossi, E
[J]. TETRAHEDRON LETTERS, 2005, 46 (42) : 7117 - 7120
[2] Azizian J., 2004, J. Chem. Res. Synop, V6, P424
[3] Silica sulfuric acid a novel and heterogeneous catalyst for the synthesis of some new oxindole derivatives
Azizian, Javad
Mohammadi, Ali A.
Karimi, Narges
Mohammadizadeh, Mohammad R.
Karimi, Ali R.
[J]. CATALYSIS COMMUNICATIONS, 2006, 7 (10) : 752 - 755
[4] Barry A.L., 1976, The Antimicrobial Susceptibility Test: Principal and Practices, V4th, P180
[5] SYNTHESIS AND STUDIES OF TRIS-INDOLOBENZENES AND RELATED-COMPOUNDS
BERGMAN, J
EKLUND, N
[J]. TETRAHEDRON, 1980, 36 (10) : 1445 - 1450
[6] BOLOTOV VV, 1982, KHIM FARM ZH+, V16, P58
[7] 1,3-DIPOLAR CYCLOADDITIONS TO NITROGEN-SUBSTITUTED ALLENES
BROGGINI, G
BRUCHE, L
ZECCHI, G
PILATI, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03): : 533 - 539
[8] Regioselective synthesis and biological evaluation of bis(indolyl)methane derivatized 1,4-disubstituted 1,2,3-bistriazoles as anti-infective agents
Damodiran, M.
Muralidharan, D.
Perumal, Paramasivan T.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (13) : 3611 - 3614
[9] Copper(II)-mediated oxidation of 1,2-dioxime to furoxan
Das, Oindrila
Paria, Sayantan
Paine, Tapan Kanti
[J]. TETRAHEDRON LETTERS, 2008, 49 (41) : 5924 - 5927
[10] Synthesis of alpha,beta-unsaturated aldehydes and methyl carboxylic esters from 2-acetylenic phenyl sulfides.
Fortes, CC
Garrote, CFD
[J]. SYNTHETIC COMMUNICATIONS, 1997, 27 (22) : 3917 - 3941

← 1 2 3 4 5 6 →