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    
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.
M Fujita; K Chiba; J Nakano; Y Tominaga; J Matsumoto
Related Documents :
15225689 - Synthesis and antibacterial activity of arylpiperazinyl oxazolidinones with diversifica...
1522419 - Antibacterial activity of crinitol and its potentiation.
15707759 - Antibacterial activity of an eudesmane sesquiterpene isolated from common varthemia, va...
3104579 - Synthesis and antimicrobial activities of n4-(2-acetoxyethoxymethyl)thiosemicarbazones ...
3546689 - Synthesis and 3'-substituent effects of some 7 alpha-methoxy-1-oxacephems on antibacter...
16446089 - Synthesis and antibacterial activity of 6-o-heteroarylcarbamoyl-11,12-lactoketolides.
23090419 - Synthesis of trans-1,3-diaryl-2-(5-methylisoxazol-3-yl)-2,3-dihydro-1h-naphtho[1,2-e][1...
10482459 - Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems. part iii:...
24520029 - Surfactant-free nonaqueous synthesis of plasmonic molybdenum oxide nanosheets with enha...
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    
Discovery Research Laboratories II, Dainippon Pharmaceutical Company, Ltd., Osaka, Japan.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Anti-Infective Agents / chemical synthesis*,  pharmacology
Microbial Sensitivity Tests
Models, Chemical
Palladium / chemistry
Quinolones / chemical synthesis*,  pharmacology
Structure-Activity Relationship
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

Previous Document:  Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically a...
Next Document:  [2-(omega-phenylalkyl)phenoxy]alkylamines: synthesis and dual dopamine2 (D2) and 5-hydroxytryptamine...