光学活性氧氟沙星的合成及抗菌活性
Synthesis and antibacterial activities of optically active ofloxacin.
作者信息
Hayakawa I, Atarashi S, Yokohama S, Imamura M, Sakano K, Furukawa M
出版信息
Antimicrob Agents Chemother. 1986 Jan;29(1):163-4. doi: 10.1128/AAC.29.1.163.
Abstract
Two optically active (100% enantiomeric excess) isomers of ofloxacin [(+/-)-ofloxacin; DL-8280; (+/-)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7 H-pyrido[1,2,3-de] [1,4] benzoxazine-6-carboxylic acid] were prepared by use of their optically resolved synthetic intermediates. One of the isomers, (-)-ofloxacin, was 8 to 128 times more potent in inhibiting the multiplication of gram-positive and gram-negative bacteria than the other, (+)-ofloxacin, and approximately two times more active than the racemate, (+/-)-ofloxacin.
摘要
通过使用其光学拆分的合成中间体制备了氧氟沙星的两种旋光异构体（对映体过量100%）[（±）-氧氟沙星；DL-8280；（±）-9-氟-2,3-二氢-3-甲基-10-（4-甲基-1-哌嗪基）-7-氧代-7H-吡啶并[1,2,3-de][1,4]苯并恶嗪-6-羧酸]。其中一种异构体，（-）-氧氟沙星，在抑制革兰氏阳性菌和革兰氏阴性菌繁殖方面的效力比另一种异构体（+）-氧氟沙星高8至128倍，并且比消旋体（±）-氧氟沙星的活性约高两倍。
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本文引用的文献
1
1,8-NAPHTHYRIDINE DERIVATIVES. A NEW CLASS OF CHEMOTHERAPEUTIC AGENTS.1,8-萘啶衍生物。一类新型化疗药物。
J Med Pharm Chem. 1962 Sep;5:1063-5. doi: 10.1021/jm01240a021.
2
Synthesis of Sch 29482--a novel penem antibiotic.新型青霉烯类抗生素Sch 29482的合成
J Antimicrob Chemother. 1982 Feb;9 Suppl C:1-5. doi: 10.1093/jac/9.suppl_c.1.
3
Synthesis and antibacterial activities of substituted 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxyl ic acids.取代的7-氧代-2,3-二氢-7H-吡啶并[1,2,3-德][1,4]苯并恶嗪-6-羧酸的合成与抗菌活性
Chem Pharm Bull (Tokyo). 1984 Dec;32(12):4907-13. doi: 10.1248/cpb.32.4907.
4
Novel amino-substituted 3-quinolinecarboxylic acid antibacterial agents: synthesis and structure-activity relationships.新型氨基取代的3-喹啉羧酸类抗菌剂：合成与构效关系
J Med Chem. 1984 Sep;27(9):1103-8. doi: 10.1021/jm00375a003.
5
Studies on quinoline derivatives and related compounds. 5. Synthesis and antimicrobial activity of novel 1-alkoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids.
J Med Chem. 1977 Jun;20(6):791-6. doi: 10.1021/jm00216a010.
6
Development of antibacterial agents of the nalidixic acid type.
Prog Drug Res. 1977;21:9-104. doi: 10.1007/978-3-0348-7098-6_1.
7
Mechanism of action of nalidixic acid: purification of Escherichia coli nalA gene product and its relationship to DNA gyrase and a novel nicking-closing enzyme.萘啶酸的作用机制：大肠杆菌nalA基因产物的纯化及其与DNA回旋酶和一种新型切口封闭酶的关系。
Proc Natl Acad Sci U S A. 1977 Nov;74(11):4767-71. doi: 10.1073/pnas.74.11.4767.
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