Synthesis of multisubstituted quinolines from Baylis-Hillman adducts obtained from substituted 2-chloronicotinaldehydes and their antimicrobial activity

被引：155
作者：
Narender, P.
Srinivas, U.
Ravinder, M.
Rao, B. Ananda
Ramesh, Ch.
Harakishore, K.
Gangadasu, B.
Murthy, U. S. N.
Rao, V. Jayathirtha
机构：
[1] Indian Inst Chem Technol, Div Biol, Hyderabad 500007, Andhra Pradesh, India
[2] Indian Inst Chem Technol, Div Organ Chem 2, Hyderabad 500007, Andhra Pradesh, India
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2006年 / 14卷 / 13期
关键词：
substituted; 2-chloronicotinaldehydes; Baylis-Hillman adducts; S(N)2 '-SNAr elimination reaction; multisubstituted quinolines; antimicrobial evaluation;
D O I：
10.1016/j.bmc.2006.02.020
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Baylis-Hillman acetates were synthesized from substituted 2-chloronicotinaldehydes and were conveniently transformed into multisubstituted quinolines and cyclopenta[g]quinolines on reaction with nitroethane or ethyl cyanoacetate via a successive S(N)2'-SNAr elimination strategy. Thus, synthesized quinolines were evaluated for antimicrobial activity and found having substantial antibacterial and antifungal activity. (c) 2006 Elsevier Ltd. All rights reserved.
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收藏
页码：4600 / 4609
页数：10
相关论文
共 59 条
[1]   Global antibiotic resistance in Streptococcus pneumoniae [J].
Adam, D .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2002, 50 :1-5
[2]   NEW CONJUGATED POLYANTHRAZOLINES CONTAINING THIOPHENE MOIETIES IN THE MAIN CHAIN [J].
AGRAWAL, AK ;
JENEKHE, SA .
MACROMOLECULES, 1991, 24 (25) :6806-6808
[3]  
ANAND RV, 1996, TETRAHEDRON LETT, V52, P8001
[4]   STEREOSELECTIVE SYNTHESIS OF OLEFINS . REACTION OF DIALKYLCOPPER-LITHIUM REAGENTS WITH ALLYLIC ACETATES [J].
ANDERSON, RJ ;
HENRICK, CA ;
SIDDALL, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) :735-&
[5]   NOVEL, POTENT, AND SELECTIVE 5-HT3 RECEPTOR ANTAGONISTS BASED ON THE ARYLPIPERAZINE SKELETON - SYNTHESIS, STRUCTURE, BIOLOGICAL-ACTIVITY, AND COMPARATIVE MOLECULAR-FIELD ANALYSIS STUDIES [J].
ANZINI, M ;
CAPPELLI, A ;
VOMERO, S ;
GIORGI, G ;
LANGER, T ;
HAMON, M ;
MERAHI, N ;
EMERIT, BM ;
CAGNOTTO, A ;
SKORUPSKA, M ;
MENNINI, T ;
PINTO, JC .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (14) :2692-2704
[6]   POTENTIAL ANTITUMOR AGENTS .57. 2-PHENYLQUINOLINE-8-CARBOXAMIDES AS MINIMAL DNA-INTERCALATING ANTITUMOR AGENTS WITH INVIVO SOLID TUMOR-ACTIVITY [J].
ATWELL, GJ ;
BAGULEY, BC ;
DENNY, WA .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (02) :396-401
[7]  
BALASUBRAMANIAN M, 1996, COMPREHENSIVE HETERO, V5, P167
[8]   Applications of Baylis-Hillman acetates:: one-pot, facile and convenient synthesis of substituted γ-lactams [J].
Basavaiah, D ;
Rao, JS .
TETRAHEDRON LETTERS, 2004, 45 (08) :1621-1625
[9]   Applications of Baylis-Hillman chemistry:: one-pot convenient synthesis of functionalized (1H)-quinol-2-ones and quinolines [J].
Basavaiah, D ;
Reddy, RM ;
Kumaragurubaran, N ;
Sharada, DS .
TETRAHEDRON, 2002, 58 (19) :3693-3697
[10]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
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