134575-66-9Relevant academic research and scientific papers
Synthesis of trovafloxacin using various (1α,5α,6α)-3-azabicyclo[3.1.0]hexane derivatives
Norris, Timothy,Braish, Tamim F.,Butters, Michael,DeVries, Keith M.,Hawkins, Joel M.,Massett, Stephen S.,Rose, Peter R.,Santafianos, Dinos,Sklavounos, Constantine
, p. 1615 - 1622 (2007/10/03)
Trovafloxacin, a novel broad spectrum antibacterial, contains the unusual (1α,5α,6α)-3-azabicyclo[3.1.0]hexane ring system. The prototype of the industrial synthesis of this ring system and possible mechanistic pathways to exclusive formation of the exo or 6α-nitro derivative 4 are described, which leads to the key 6a-nitro-3-azabicyclo[3.1.0]hexane intermediate 10. The synthesis of 6a-amino-3-azabicyclo[3.1.0]hexane 16 and useful protected cxo 6-amino derivatives 15 and 17 follows from 10. These can be coupled with the 7-chloronaphthyridone 18 to yield protected trovafloxacin compounds 20-22 in good yield. The ethyl ester of trovafloxacin 21 can also be accessed from the product of coupling 19, derived from 18 and the exo 6-nitro-3-azabicyclo[3.1.0]hexane compound 12. Removal of protecting groups from 20-22 with methanesulfonic acid yields trovafloxacin mesylate from which trovafloxacin zwitterion 1 can be liberated with base treatment. Zwitterion l can also be prepared directly from 16 tosylate salt and naphthyridone-2-carboxylic acid 26. The Royal Society of Chemistry 2000.
Azabicyclo quinolone carboxylic acids
-
, (2008/06/13)
Quinolone carboxylic acids 7-substituted by azabicyclo groups have antibacterial activity., Antibacterial wherein, R1 is hydrogen, a pharmaceutically acceptable cation, or alkyl;, Y, when taken independently, is ethyl, t-butyl, vinyl, cyclopropyl, 2-fluoroethyl, p-fluorophenyl, or o,p-difluorophenyl;, W is hydrogen, F, Cl, Br, alkyl, alkoxy, NH2, NHCH3;, A is CH, CF, CCl, COCH3, C-CH3, C-CN or N; or, A is carbon and is taken together with Y and the carbon and nitrogen to which A and Y are attached to form a five or six membered ring which may contain oxygen or a double bond, and which may have attached thereto R8 which is methyl or methylene; and, R2 is wherein R3, R4, R5, R6, R7, R9, R10 and R25 are each independently H, CH3, CH2NH2, CH2NHCH3 or CH2NHC2H5, and R5, R6, R7, and R9 may also independently be NH2, NHCH3 or NHC2H5.
