CAS: 209342-41-6; 8-Cyano-1-Cyclopropyl-6-Fluoro-7-((4As,7As)-Hexahydropyrrolo[3,4-B][1,4]Oxazin-6(2H)-yl)-4-Oxo-1,4-Dihydroquinoline-3-Carboxylic Acid Hydrochloride

该化合物是一种氟己酮抗生素,在酸性环境中的活动增强,使其在低pH条件下,如尿道感染,对细菌感染特别有效,其独特的pH值依赖抗菌素特征使得能够有针对性地有效防治包括抗药性菌株在内的克模阳性和克格阴性病原体;盐的盐形式提高了溶性和生物利用率,促进了配方的开发;氢氯氟化碳表现出了广泛频谱的活动,细菌DNA甘蓝和四角异构体酶受到强烈抑制.

英文名称8-Cyano-1-Cyclopropyl-6-Fluoro-7-((4As,7As)-Hexahydropyrrolo[3,4-B][1,4]Oxazin-6(2H)-yl)-4-Oxo-1,4-Dihydroquinoline-3-Carboxylic Acid Hydrochloride
中文名称非那沙星
IUPAC名称8-cyano-1-cyclopropyl-6-fluoro-7-((4aS,7aS)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
其它别名7-[(4As,7As)-3,4,4A,5,7,7A-Hexahydro-2H-Pyrrolo[3,4-B][1,4]Oxazin-6-Yl]-8-Cyano-1-Cyclopropyl-6-Fluoro-4-Oxoquinoline-3-Carboxylic Acid,Hydrochloride; Finafloxacin Hydrochloride; 8-Cyano-1-Cyclopropyl-6-Fluoro-7-[(4As,7As)-Hexahydropyrrolo[3,4-B]-1,4-Oxazin-6(2H)-Yl]-1,4-Dihydro-4-Oxo-3-Quinolinecarboxylic Acid Hydrochloride; 8-Cyano-1-Cyclopropyl-6-Fluoro-7-((4As,7As)-Hexahydropyrrolo[3,4-B][1,4]Oxazin-6(2H)-yl)-4-Oxo-1,4-Dihydroquinoline-3-Carboxylic Acid Hydrochloride; 8-Cyano-1-Cyclopropyl-6-Fluoro-7-[(4As,7As)-Hexahydropyrrolo[3,4-B]-1,4-Oxazin-6(2H)-Yl]-1,4-Dihydro-4-Oxo-3-Quinolinecarboxylic Acid Monohydrochloride; 3-Quinolinecarboxylic Acid, 8-Cyano-1-Cyclopropyl-6-Fluoro-7-[(4As,7As)-Hexahydropyrrolo[3,4-B]-1,4-Oxazin-6(2H)-Yl]-1,4-Dihydro-4-Oxo-, Monohydrochloride (9Ci); 8-Cyano-1-Cyclopropyl-6-Fluoro-7-((4As,7As)-Hexahydropyrrolo[3,4-B][1,4]Oxazin-6(2H)-yl)-4-Oxo
CAS编号209342-41-6
MFCD编号:MFCD23160294
FDA UNII编号:2G22PNZ052
分子式:C20H20ClFN4O4分子量:434.86
产品CID: 1071924
产品分类原料药 → 人工合成抗感染类药 → 喹诺酮类药

相似结构搜索
InChIKey: CQMSQUOHWYYEKM-MOGJOVFKSA-N
InChI=1S/C20H19FN4O4.ClH/c21-14-5-11-17(25(10-1-2-10)7-13(19(11)26)20(27)28)12(6-22)18(14)24-8-15-16(9-24)29-4-3-23-15;/h5,7,10,15-16,23H,1-4,8-9H2,(H,27,28);1H/t15-,16-;
计算化学: 氢键受体数9.0氢键供体数3.0可旋转键数3.0

物理性质

熔点>210°C (分解)
闪点368.8 °C
PSA:107.59
LogP:2.41818
蒸汽压9.03E-20 mmHg at 25 °C
溶解性Aqueous Base (Very Slightly), DMSO (Slightly, Sonicated)
外观形态浅棕色至棕色固体
储存条件防潮, -20°C 冰箱, 在惰性气其中
产品应用该化合物用于制作环丙烯酮盒状酸衍生物,作为治疗乙醇杆菌感染和相关肠道疾病药物.

MSDS等安全信息

GHS符号GHS07
警示词Warning
危险描述H302-H315-H319-H335
防范说明P261-P280-P301+P312-P302+P352-P305+P351+P338

上下游产品

ethyl 8-cyano-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate base 1S,6S-2-oxa-5,8-diazabicyclo[4.3.0]nonane 25H27FN4O6C25H27FN4O6

合成工艺路线路线简述

📜在盐酸体系中,用乙醚,乙醇用作溶剂,以85%的收率获得非那沙星
参考文献:A Novel Approach To Finafloxacin Hydrochloride (Bay35-3377)
标题:A Novel Approach To Finafloxacin Hydrochloride (Bay35-3377)
摘要:Finafloxacin Hydrochloride,An Important Clinical Compound Was Synthesized By A Novel Synthetic Approach. An Active Intermediate Ethyl 7-Chloro-8-Cyano-1-Cyclopropyl-6-Fluoro-4-Oxo-1,4-Dihydro-Quinoline-3-Carboxylate 19 Was Prepared By A New Route. The Chiral (S,S')-N-Boc 10 Was Derived From Protected Pyrrolidine And The Absolute Stereochemistry Was Established By X-Ray Analysis. (C) 2009 Elsevier Ltd. All Rights Reserved.
Doi:10.1016/j.Tetlet.2009.03.051