A novel approach to Finafloxacin hydrochloride (BAY35-3377)

被引:22
作者
Hong, Jian [1 ]
Zhang, Zonghua [1 ]
Lei, Huoxing [1 ]
Cheng, Haiying [1 ]
Hu, Yufang [1 ]
Yang, Wanliang [1 ]
Liang, Yinglin [1 ]
Das, Debasis [1 ]
Chen, Shu-Hui [1 ]
Li, Ge [1 ]
机构
[1] WuXi AppTec Inc, Shanghai 200131, Peoples R China
关键词
Finafloxacin hydrochloride; BAY35-3377; Fluoroquinolone antibiotics; MYCOBACTERIUM-TUBERCULOSIS; QUINOLONE ANTIBACTERIALS; FLUOROQUINOLONES; DERIVATIVES; MECHANISM; DESIGN; AGENTS;
D O I
10.1016/j.tetlet.2009.03.051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
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.
引用
收藏
页码:2525 / 2528
页数:4
相关论文
共 42 条
[21]   SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 1-CYCLOPROPYL-6,8-DIFLUORO-7-(2-SUBSTITUTED 4,6-DIHYDRO-1H-PYRROLO[3,4-D]THIAZOL-5-YL)-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID [J].
KIM, WJ ;
KIM, BJ ;
LEE, TS ;
NAM, KS ;
KIM, KJ .
HETEROCYCLES, 1995, 41 (07) :1389-1397
[22]   STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTI-BACTERIAL 6,7-DISUBSTITUTED AND 7,8-DISUBSTITUTED 1-ALKYL-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACIDS [J].
KOGA, H ;
ITOH, A ;
MURAYAMA, S ;
SUZUE, S ;
IRIKURA, T .
JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (12) :1358-1363
[23]   1,8-NAPHTHYRIDINE DERIVATIVES - A NEW CLASS OF CHEMOTHERAPEUTIC AGENTS [J].
LESHER, GY ;
GRUETT, MD ;
FROELICH, EJ ;
BRUNDAGE, RP ;
BAILEY, JH .
JOURNAL OF MEDICINAL & PHARMACEUTICAL CHEMISTRY, 1962, 5 (05) :1063-&
[24]   Thermochemical reaction of 7-azido-1-ethyl-6,8-difluoroquinolone-3-carboxylate with heterocyclic amines. An expeditious synthesis of novel fluoroquinolone derivatives [J].
Leyva, Socorro ;
Leyva, Elisa .
TETRAHEDRON, 2007, 63 (09) :2093-2097
[25]   Using SAR and QSAR analysis to model the activity and structure of the quinolone-DNA complex [J].
Llorente, B ;
Leclerc, F ;
Cedergren, R .
BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (01) :61-71
[26]   Novel quinolone derivatives as potent antibacterials [J].
Lohray, BB ;
Baskaran, S ;
Rao, BS ;
Mallesham, B ;
Bharath, KSN ;
Reddy, BY ;
Venkateswarlu, S ;
Sadhukhan, AK ;
Kumar, MS ;
Sarnaik, HM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (05) :525-528
[27]   Synthesis and antimicrobial activity of 4H-4-Oxoquinolizine derivatives:: Consequences of structural modification at the C-8 position [J].
Ma, ZK ;
Chu, DTW ;
Cooper, CS ;
Li, Q ;
Fung, AKL ;
Wang, SY ;
Shen, LL ;
Flamm, RK ;
Nilius, AM ;
Alder, JD ;
Meulbroek, JA ;
Or, YS .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (20) :4202-4213
[28]  
Marians KJ, 1997, J BIOL CHEM, V272, P9401
[29]  
Matzke M., 2000, US Patent, Patent No. [6133260A, 6133260]