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1.
J. M. Ruxer C. Lachoux J. B. Ousset J. L. Torregrosa G. Mattioda 《Journal of heterocyclic chemistry》1994,31(2):409-417
To check the antibacterial potential of two families of aza analogues of the quinolones, 1,4-dihydro-4-oxopyrrolo[1,2-b]pyridazine-3-carboxylic acids and 1,4-dihydro-4-oxoimidazo[1,5-b]pyridazine-3-carboxylic acids, we have prepared a few derivatives in theses families using N-aminopyrrole and N-aminoimidazole derivatives as starting building blocks and the classical pathways of the quinolone series. The compounds showed no interesting antibacterial activity. 相似文献
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H Miyamoto H Ueda T Otsuka S Aki H Tamaoka M Tominaga K Nakagawa 《Chemical & pharmaceutical bulletin》1990,38(9):2472-2475
A series of substituted 4-oxoquinoline-3-carboxylic acids having a methyl group at the 8-position was prepared and tested for their antibacterial activity. 7-(trans-3-Amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-1,4-dihydro-6- fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid (21) exhibited highly potent antibacterial activity against both gram-positive and gram-negative bacteria, including Pseudomonas aeruginosa. 相似文献
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Philippe Remuzon Daniel Bouzard Pierre Di Cesare Christian Dussy Jean-Pierre Jacquet Alexandre Jaegly 《Journal of heterocyclic chemistry》1992,29(4):985-989
The 5-hydroxymethyl and the 5-formyl-1-cyclopropyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared via a 5-trimethylsilyl group and were tested in vitro as potential antibacterials. 相似文献
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Jia-Yuh Sheu Yeh-Long Chen Kuo-Chang Fang Tai-Chi Wang Cherng-Chyi Tzeng Chien-Fang Peng 《Journal of heterocyclic chemistry》1998,35(4):955-964
Alkylation of 6,7-difluoro-4-hydroxyquinoline-3-carboxylic acid ethyl ester with substituted-benzyl chlorides gave 1-(substituted-benzyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl esters. Their treatment with piperazine or N-methylpiperazine in pyridine yielded 1-(substituted-benzyl)-6-fluoro-1,4-dihydro-4-oxo-7-(l-piperazinyl)quinoline-3-carboxylic acid ethyl esters which were hydrolyzed with aqueous sodium hydroxide and then acidified with hydrochloric acid afforded the desired 1-(substituted-benzyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-iperazinyl)quinoline-3-carboxylic acids. The 6,8-difluoro analogs were prepared similarly using 6,7,8-trifluoro-4-hydroxyquinoline-3-carboxylic acid ethyl ester as a starting material. Some of these quinolones demonstrated fairly good antibacterial activities. Among them, 6-fluoro-1-(4-fluorophenylmethyl)-1,4-dihydro-7-(1-iperazinyl)-4-oxoquinoline-3-carboxylic acid ( 7d ) and 6,8-difluoro-1-(3-fluorophenylmethyl)-1,4-dihydro-7-(1-piperazinyl)-4-oxoquinoline-3-carboxylic acid ( 8c ) are two of the best. 相似文献
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By the displacement reactions of 1-ethyl-4-chloro-3-carboethoxy-6,7-methylenedioxyquinolinium iodide ( 3a ), several 4-substituted derivatives including the 4-thioxo ( 1c ) and 4-amino derivatives ( 6 ) of oxolinic acid were prepared. The acid 1c and its N1-substituted derivatives ( 18a-h ) were prepared alternatively by alkylation of ethyl 4-ethylmercapto-6,7-methylenedioxy-3-quinolinecarboxylate ( 15 ) followed by treatment with sodium hydrosulfide and hydrolysis. 相似文献
7.
Teruyuki Miyamoto Hiroshi Egawa Koh-Ichiro Shibamori Jun-Ichi Matsuraoto 《Journal of heterocyclic chemistry》1987,24(5):1333-1339
1-Cyclopropyl- and 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid derivatives having a sulfinyl or sulfonyl group at C-7 were synthesized from 2,6-dichloro-5-fluoronicotinic acid derivatives by the route involving the Dieckmann-type cyclization. The displacement reactions of these compounds with pyrrolidine and piperidine gave mainly the 7-(1-pyrrolidinyl)- and 7-(1-piperidinyl)-1,8-naphthyridine derivatives 24-27 , respectively. Enoxacin, a potent antibacterial agent, was also synthesized with the analogous route. 相似文献
8.
Hideo Agui Toru Mitani Mitsuo Nakashita Takenari Nakagome 《Journal of heterocyclic chemistry》1971,8(3):357-365
A novel preparative method for 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids was developed. The key process is the cyclization of N-alkylanilinomethylenemalonales, which was effected successfully in the presence of polyphosphoric acid, polyphosphate ester, boron tri-fluoride or a mixture of acetic anhydride and sulfuric acid. With phosphorus oxychloride, N-alkylanilinomethylenemalonates yielded 1-alkyl-4-chloro-3-carbethoxyquinolinium salts which were hydrolyzed readily to ethyl 1-alkyl-1,4-dihydro-4-oxo-3-quinolineearboxylates or their acids. By means of this novel method several new 1-alkyl-1,4-dihydro-4-oxo-3-quinolineearboxylic acids were prepared. 相似文献
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Y Nishimura T Hirose H Okada K Shibamori J Nakano J Matsumoto 《Chemical & pharmaceutical bulletin》1990,38(8):2190-2196
A series of C-7 thio-substituted 1-cyclopropyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids were prepared and tested for their antibacterial activity. Structure-activity relationships associated with the C-5 and C-7 substituents were discussed. Among the C-7 substituents including alkylthio, arylthio, heteroarylthio, and cyclic aminothio groups, a 2-aminoethylthio group was the best for enhancing in vitro antibacterial activity. The C-5 variants increased activity in the order OH less than F less than H less than NH2. Of compounds prepared in this work, 5-amino-7-(2-aminoethyl)thio-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4 -oxo-quinoline-3-carboxylic acid (18) was the most active. 相似文献
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Carl B. Ziegler William V. Curran Nydia A. Kuck Sonja M. Harris Yang-I. Lin 《Journal of heterocyclic chemistry》1989,26(4):1141-1145
A series of 7-substituted 1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acids were prepared from 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 8 . Those derivatives reported contain acyclic and heterocyclic substituents linked to the quinolone C-7 position via O, NH or S. The in vitro antibacterial data of some of these derivatives against 4 Gram positive and 4 Gram negative organisms are reported. 相似文献
12.
J. M. Ruxer C. Lachoux J. B. Ousset J. L. Torregrosa G. Mattioda 《Journal of heterocyclic chemistry》1994,31(6):1561-1568
A few aza analogues of the quinolones have been prepared in the two families of the 1,4-dihydro-4-oxopyridazino[1,6-a]indole-3-carboxylic acids and the 1,4-dihydro-4-oxopyrido[3′,2′:4,5]pyrrolo[1,2-b]-pyridazine-3-carboxylic acids to check their antibacterial potential. One compound 6c shows antibacterial activities of the level of nalidixic acid and represents a new lead structure differing from the classical quinolones. 相似文献
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Acetylation of 2-arylamino-5-carbethoxy-6-methylnicotinonitriles gave N-acetyl-2-arylamino-5-carbethoxy-6-methylnicotinonitriles, which, under the influence of hydrogen chloride, are cyclized to 1-aryl-1,4-dihydro-6-carbethoxy-2,7-dimethyl-4-oxopyrido[2,3-d]pyrimidines. The latter can be converted to the corresponding carboxylic and hydroxamic acids, as well as to acetylation products 1-aryl-2-acetonyl-1,4-dihydro-6-carbethoxy-7-methyl-4-oxopyrido [2,3-d]pyrimidines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 535–539, April, 1992. 相似文献
15.
A general method tor the preparation of 1,4-dihydro-4-quinolone-2-carboxylic acids, especially those which carry alkyl substituents on the ring N-atom, is described. 相似文献
16.
Said M. Bayomi Kenneth E. Price J. Walter Sowell 《Journal of heterocyclic chemistry》1985,22(3):729-734
A route for the synthesis of various derivatives of 1,4-dihydro-4-oxopyrrolo[3,4-b]pyridine-3-carboxylic acid from 2-phenyl-3-amino-4-t-butoxycarbonyl-5-methylpyrrole hydrochloride is reported. 相似文献
17.
The cyclization of m-substituted anilinomethylenemalonates ( 1 ) in the presence of polyphosphate ester and some other cyclizing agents gave mixtures of the isomeric ethyl 5- ( 2 ) and 7-substituted 4-hydroxy-3-quinolinecarboxylates ( 3 ), which led to mixtures of the corresponding quinolinecarboxylic acids ( 4 and 5 ) by hydrolysis. The proportions of 4 and 5 in the mixtures were determined on the basis of their nmr spectra. Novel 5-chloro- ( 8a ), 5-methyl- ( 8b ) and 5-nitro-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids were prepared and evaluated for antimicrobial activities. No significant activity, however, was noted. 相似文献
18.
A series of 7-amino-1-cyclopropyl-1,4-dihydro-8-fluoro-4-oxo-1,6-naphthyridine-3-carboxylic acids has been prepared and evaluated for antibacterial activity. These compounds were prepared by the displacement of the chloro substituent from 7-chloro-1-cyclopropyl-1,4-dihydro-8-fluoro-4-oxo-1,6-naphthyridine-3-carboxylic acid employing the requisite nitrogen nucleophile to produce the title compounds. The naphthyridine acid was synthesized in ten steps from ethyl 2,4-dihydroxy-3-nitro-5-pyridinecarboxylate. The key step in the sequence was a Schiemann reaction carried out using the hexafluorophosphate salt of the diazonium ion derived from ethyl 3-amino-2,4-dichloro-5-pyridinecarboxylate. 相似文献
19.
The preparation of a variety of 8-cyano-1,4-dihydro-7-phenyl-4-oxopyrrolo[1,2-a]pyrimidine-3-carboxylicacids and 8-cyano-1,4-dihydro-7-p-fluorophenyl-4-oxopyrrolo[1,2-a]pyrimidine-3-carboxylic acids is described. 相似文献