4-HYDROXY-2-QUINOLONES. 194. 1-HYDROXY-3-OXO-6,7-DIHYDRO-3H,5H-PYRIDO[3,2,1-ij]QUINOLINE-2-CARBOXYLIC ACID ALKYLAMIDES. SYNTHESIS, STRUCTURE, AND BIOLOGICAL PROPERTIES

被引:4
作者
Ukrainets, I. V. [1 ]
Golik, N. Yu. [1 ]
Andreeva, K. V. [1 ]
Gorokhova, O. V. [1 ]
机构
[1] Natl Univ Pharm, UA-61002 Kharkov, Ukraine
关键词
4-hydroxy-2-oxoquinoline-3-carboxylic acid alkylamides; amidation; diuretic activity; X-ray structural analysis;
D O I
10.1007/s10593-011-0692-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Modified methods are proposed for the preparation of the ethyl ester and alkylamides of 1-hydroxy-3- oxo-6,7-dihydro-3H, 5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid. A comparative analysis has been carried out of the steric structure and diuretic activity of the synthesized compounds and the previously studied, and closely structurally related, 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo-[3,2,1-ij]quinoline-2-carboxamides.
引用
收藏
页码:1459 / 1466
页数:8
相关论文
共 14 条
[1]  
[Anonymous], 2007, Chem. Heterocycl. Compd, DOI DOI 10.1007/S10593-007-0220-9
[2]  
Burgi H.-B., 1994, Structure Correlation, P741, DOI [10.1002/9783527616091, DOI 10.1002/9783527616091]
[3]   Methanetricarboxylates as key reagents for the simple preparation of heteroarylcarboxamides with potential biological activity .1. Reaction of methanetricarboxylates with indoline and 1,2,3,4-tetrahydroquinoline [J].
Kutyrev, A ;
Kappe, T .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (03) :969-972
[4]  
MASHKOVSKII MD, 2009, DRUGS, P502
[5]  
MOSPANAOVA EV, 2008, THESIS KHARKIV
[6]  
NABOKA OI, 2009, THESIS KIEV
[7]  
SERNOV LN, 2000, ELEMENTS EXPT PHARM, P103
[8]   A short history of SHELX [J].
Sheldrick, George M. .
ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 :112-122
[9]   Methyl 2-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)acetate [J].
Shishkina, Svitlana V. ;
Shishkin, Oleg V. ;
Ukrainets, Igor V. ;
Mospanova, Elena V. .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 :O3195-U877
[10]   4-HYDROXY-2-QUINOLONES 148. SYNTHESIS AND ANTI-TUBERCULAR ACTIVITY OF 1-HYDROXY-3-OXO-6,7-DIHYDRO-3H,5H-PYRIDO[3,2,1-ij]QUINOLINE-2-CARBOXYLIC ACID N-R-AMIDES [J].
Ukrainets, I. V. ;
Tkach, A. A. ;
Grinevich, L. A. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (08) :956-966