New 7‐substituted quinolone antibacterial agents. The synthesis of 1‐ethyl‐1,4‐dihydro‐4‐oxo‐7‐(2‐thiazolyl and 4‐thiazolyl)‐3‐quinolinecarboxylic acids

作者: Townley P. Culbertson , John M. Domagala , Phred Peterson , Shannon Bongers , Jeffrey B. Nichols

DOI: 10.1002/JHET.5570240604

关键词: ChemistryMoietyThiazoleMedicinal chemistryAntibacterial activityOrganic chemistryAmine gas treatingBiological activityBicyclic moleculeThioamideAntibacterial agent

摘要: A series of 1-ethyl-1,4-dihydro-4-oxo-7-(4-thiazolyl)-3-quinolinecarboxylic acids and 1-ethyl-1,4-dihydro-4-oxo-7-(2-thiazolyl)-3-quinolinecarboxylic were prepared. Also prepared was 10-[2-(aminomethyl)-4-thiazolyl]-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid. Analogs with basic amine substituents on the thiazole moiety found to have antibacterial activity.

参考文章(17)
G. A. Bihlmayer, G. Derflinger, J. Derkosch, O. E. Polansky, Oxy- und Aminomethylenmeldrumsäuren Monatshefte Fur Chemie. ,vol. 98, pp. 564- 578 ,(1967) , 10.1007/BF00901364
Kishorkant J. Shah, Eugene A. Coats, Design, synthesis, and correlation analysis of 7-substituted 4-hydroxyquinoline-3-carboxylic acids as inhibitors of cellular respiration. Journal of Medicinal Chemistry. ,vol. 20, pp. 1001- 1006 ,(1977) , 10.1021/JM00218A003
Dennis M. Mulvey, A.M. DeMarco, L.M. Weinstock, A novel synthesis of fluoroaromatics Tetrahedron Letters. ,vol. 19, pp. 1419- 1420 ,(1978) , 10.1016/S0040-4039(01)94562-9
Philip M. Carabateas, R. Pauline Brundage, Karl O. Gelotte, Monte D. Gruett, Roman R. Lorenz, Chester J. Opalka, Baldev Singh, William H. Thielking, Gordon L. Williams, George Y. Lesher, 1‐Ethyl‐1,4‐dihydro‐4‐oxo‐7‐(pyridinyl)‐3‐quinolinecarboxylic acids. I. Synthesis of 3‐ and 4‐(3‐aminophenyl)pyridine intermediates Journal of Heterocyclic Chemistry. ,vol. 21, pp. 1849- 1856 ,(1984) , 10.1002/JHET.5570210654
Hiroshi Koga, Akira Itoh, Satoshi Murayama, Seigo Suzue, Tsutomu Irikura, Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids Journal of Medicinal Chemistry. ,vol. 23, pp. 1358- 1363 ,(1980) , 10.1021/JM00186A014
William O. Foye, Joel M. Kauffman, Antiradiation compounds. XI. Sulfur-containing derivatives of nitriles and aminonitriles. Journal of Pharmaceutical Sciences. ,vol. 57, pp. 1614- 1616 ,(1968) , 10.1002/JPS.2600570933
Hans Reihlen, G. v. Hessling, W. Hühn, E. Weinbrenner, Über aliphatische 1,2-Diamine Justus Liebig's Annalen der Chemie. ,vol. 493, pp. 20- 32 ,(1932) , 10.1002/JLAC.19324930103
Yasuhiko Seto, Kazuhira Torii, K\={o}ichi Bori, Kenichiro Inabata, Shigeru Kuwata, Hiroshi Watanabe, Studies of Unusual Amino Acids and Their Peptides. V. The Synthesis and the Absolute Configuration of β(2-Thiazolyl)-β-alanine Present in Bottromycin Bulletin of the Chemical Society of Japan. ,vol. 47, pp. 151- 155 ,(1974) , 10.1246/BCSJ.47.151
Ted T. Sakai, James M. Riordan, Thomas E. Booth, Jerry D. Glickson, Synthesis and DNA binding of [3-[2'-(2-acetamidoethyl)-2,4'-bithiazole-4-carboxamido]propyl[dimethylsulfonium chloride, a fragment of bleomycin A2. Journal of Medicinal Chemistry. ,vol. 24, pp. 279- 285 ,(1981) , 10.1021/JM00135A008
John M. Domagala, Lori Doyle Hanna, Carl L. Heifetz, Marland P. Hutt, Thomas F. Mich, Joseph P. Sanchez, Marjorie Solomon, New structure-activity relationships of the quinolone antibacterials using the target enzyme. The development and application of a DNA gyrase assay Journal of Medicinal Chemistry. ,vol. 29, pp. 394- 404 ,(1986) , 10.1021/JM00153A015