4-HYDROXY-2-QUINOLONES 171*. SYNTHESIS, ISOMERISM, AND ANTITUBERCULAR ACTIVITY OF 1-R-4-HYDROXY-2-OXO-1,2-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ALKYLIDENEHYDRAZIDES

被引：2

作者：

Ukrainets, I. V. ^{[1
]}

Liu Yangyang ^{[1
]}

Tkach, A. A. ^{[1
]}

Turov, A. V. ^{[2
]}

Golovchenko, O. S. ^{[1
]}

机构：

[1] Natl Univ Pharm, UA-61002 Kharkov, Ukraine

[2] Taras Shevchenko Natl Univ, UA-01033 Kiev, Ukraine

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2009年 / 45卷 / 11期

关键词：

hydrazones; 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids; isomerism; antitubercular activity; IN-VITRO; HYDRAZONES; DERIVATIVES; ISONICOTINOYLHYDRAZONES; HYDRAZIDES;

D O I：

10.1007/s10593-010-0431-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylidenehydrazides have been synthesized by the reaction of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazides with lower dialkyl ketones in order to reveal a structure-antitubercular activity relationship. It was shown by H-1 NMR spectroscopy that hydrazones obtained from the unsymmetrical ketone-methyl ethyl ketone-exist primarily in the E-isomer form. It was found that the presence of two aliphatic substituents in the alkylidene fragment of the compounds investigated leads to a marked lowering of antimicobacterial properties.

引用

页码：1335 / 1342

页数：8

共 23 条

[1] BAGROV FV, 2002, ZH ORG KHIM, V38, P1364
[2] New heterocyclic hydrazones in the search for antitubercular agents:: Synthesis and in vitro evaluations
Bijev, A.
[J]. LETTERS IN DRUG DESIGN & DISCOVERY, 2006, 3 (07) : 506 - 512
[3] Bijev A, 2006, ARZNEIMITTELFORSCH, V56, P96
[4] Activity of a new class of isonicotinoylhydrazones used alone and in combination with isoniazid, rifampicin, ethambutol, para-aminosalicylic acid and clofazimine against Mycobacterium tuberculosis
De Logu, A
Onnis, V
Saddi, B
Congiu, C
Schivo, ML
Cocco, MT
[J]. JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2002, 49 (02) : 275 - 282
[5] Heifets L.B., 1991, DRUG SUSCEPTIBILITY, P89
[6] Inderlied C.B., 1996, Antibiotics in laboratory medicine, V4th, P127
[7] KUZNETSOV SG, 1991, SUMMARIES SOURCES SC, V19, P25
[8] In vitro advanced antimycobacterial screening of isoniazid-related hydrazones, hydrazides and cyanoboranes:: Part 14
Maccari, R
Ottanà, R
Vigorita, MG
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (10) : 2509 - 2513
[9] MASHKOVSKII MD, 2002, DRUGS, V2, P306
[10] PETRUKH LI, 1999, FARMAKOM, P9

← 1 2 3 →