Synthesis and antibacterial activity of new fluoroquinolones containing a substituted N-(phenethyl)piperazine moiety

被引:87
作者
Foroumadi, Alireza [1 ]
Ghodsi, Shahram
Emami, Saeed
Najjari, Somayyeh
Samadi, Nasrin
Faramarzi, Mohammad Ali
Beikmohammadi, Leila
Shirazi, Farshad H.
Shafiee, Abbas
机构
[1] Univ Tehran Med Sci, Fac Pharm & Pharmaceut Sci, Res Ctr, Tehran 14174, Iran
[2] Islamic Azad Univ, Fac Sci, Dept Chem, Karaj Branch, Karaj, Iran
[3] Mazandaran Univ Med Sci, Sari 48175, Iran
[4] Shahid Beheshti Univ Med Sci, Fac Pharm, Dept Pharmacol & Toxicol, Tehran, Iran
关键词
piperazinyl quinolones; ciprofloxacin derivatives; antimicrobial activity; methoxyimino-substituent;
D O I
10.1016/j.bmcl.2006.03.103
中图分类号
R914 [药物化学];
学科分类号
100701 [药物化学];
摘要
N-(Phenethyl)piperazinyl quinolone derivatives that bear a methoxyimino-substituent have been synthesized and evaluated for antimicrobial activity against Gram-positive and Gram-negative microorganisms. In addition, to define structure-activity relationships, ciprofloxacin derivatives containing 2-oxo-2-phenylethyl or 2-hydroxyimino-2-phenylethyl moieties at N-4 position of piperazine ring were prepared and tested. Ciprofloxacin derivatives, containing a N-(chloro-substituted phenethyl) residue, showed in vitro Gram-positive and Gram-negative activity generally comparable or superior to that of reference quinolones. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3499 / 3503
页数:5
相关论文
共 26 条
[1]
Type II topoisomerases as targets for quinolone antibacterials: turning Dr. Jekyll into Mr. Hyde [J].
Anderson, VE ;
Osheroff, N .
CURRENT PHARMACEUTICAL DESIGN, 2001, 7 (05) :337-353
[2]
Comparative tolerability of the newer fluoroquinolone antibacterials [J].
Ball, P ;
Mandell, L ;
Niki, Y ;
Tillotson, G .
DRUG SAFETY, 1999, 21 (05) :407-421
[3]
Quinolone-induced QT interval prolongation: a not-so-unexpected class effect [J].
Ball, P .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2000, 45 (05) :557-559
[4]
BARON EJ, 1990, BAILEY SCOTTS DIAGNO, P184
[6]
ROUTES OF QUINOLONE PERMEATION IN ESCHERICHIA-COLI [J].
CHAPMAN, JS ;
GEORGOPAPADAKOU, NH .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1988, 32 (04) :438-442
[7]
In vitro antibacterial activity and phamacodynamics of new quinolones [J].
Dalhoff, A ;
Schmitz, FJ .
EUROPEAN JOURNAL OF CLINICAL MICROBIOLOGY & INFECTIOUS DISEASES, 2003, 22 (04) :203-221
[8]
De Sarro A, 2001, CURR MED CHEM, V8, P371
[9]
NEW STRUCTURE-ACTIVITY-RELATIONSHIPS OF THE QUINOLONE ANTIBACTERIALS USING THE TARGET ENZYME - THE DEVELOPMENT AND APPLICATION OF A DNA GYRASE ASSAY [J].
DOMAGALA, JM ;
HANNA, LD ;
HEIFETZ, CL ;
HUTT, MP ;
MICH, TF ;
SANCHEZ, JP ;
SOLOMON, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (03) :394-404
[10]
Structural features of new quinolones and relationship to antibacterial activity against gram-positive bacteria [J].
Emami, S ;
Shafiee, A ;
Foroumadi, A .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2006, 6 (04) :375-386