Document Detail


Synthesis and structure--antibacterial activity relationships of 7-(3-amino-1-propynyl and 3-amino-1-propenyl)quinolones.
MedLine Citation:
PMID:  9579039     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
7-(3-Amino-1-propynyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4- oxoquinoline-3-carboxylic acid (7a) and some related compounds (7b-f, 8a, b, 9) were prepared via palladium(0)-catalyzed cross-coupling reaction of 7-iodoquinolone 12 with acetylenic compounds and their antibacterial activity was tested. The methylene homologue (7d) and the N-methyl derivative (7e) of 7a showed essentially the same activity as that of 7a. Addition of methyl group(s) to C'-3 of 7a (giving 7b, c) reduced the activity. The hydrogenation of 7a to (Z)-3-amino-1-propenyl (8a), (E)-3-amino-1-propenyl (8b) and 3-amino-1-propyl (9) compounds retained or enhanced the activity of 7a. Among the compounds prepared, 8a was the most active, but was less active than ciprofloxacin (1). In order to get insight into structure-activity relationships, the spatial distribution of the amino groups of 7a, 8a, b, and 9 was examined by means of computer-aided molecular modeling.
Authors:
M Fujita; K Chiba; J Nakano; Y Tominaga; J Matsumoto
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  46     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  1998 Apr 
Date Detail:
Created Date:  1998-06-04     Completed Date:  1998-06-04     Revised Date:  2003-11-14    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  631-8     Citation Subset:  IM    
Affiliation:
Discovery Research Laboratories II, Dainippon Pharmaceutical Company, Ltd., Osaka, Japan.
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MeSH Terms
Descriptor/Qualifier:
Anti-Infective Agents / chemical synthesis*,  pharmacology
Catalysis
Fluoroquinolones
Microbial Sensitivity Tests
Models, Chemical
Palladium / chemistry
Quinolones / chemical synthesis*,  pharmacology
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Anti-Infective Agents; 0/Fluoroquinolones; 0/Quinolones; 7440-05-3/Palladium

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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