Document Detail


Synthesis, stereochemistry and antimicrobial evaluation of some N-morpholinoacetyl-2,6-diarylpiperidin-4-ones.
MedLine Citation:
PMID:  17275965     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
In a search for new leads towards potent antimicrobial agents, an array of novel N-morpholinoacetyl-2,6-diarylpiperidin-4-ones has been synthesized and their in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi and antifungal activity against Candida albicans, Rhizopus sp., Aspergillus niger and Aspergillus flavus were evaluated. Structure and stereochemistry of all the N-morpholinoacetyl-2,6-diarylpiperidin-4-ones have been analyzed using (1)H and (13)C NMR spectroscopic techniques. In all the cases, amide N-CO group is preferentially in coplanar orientation with respect to the dynamically averaged plane of the piperidone ring. Further, all the symmetrically substituted compounds 19, 23, 24, 26 and 27 are expected to adopt half boat conformations while other compounds 20-22 and 25 adopt twist-boat conformations. Structure-activity relationship results for these nine compounds have shown that compounds 26 and 27 exerted excellent antibacterial activity against all the bacterial strains used except 27 against S. aureus. Against C. albicans and A. flavus, compound 24 recorded excellent antifungal activities while against Rhizopus sp., compound 25 showed potent activities. The obtained results may be used as key step for the building of novel chemical compounds with interesting antimicrobial profiles comparable to that of the standard drugs.
Authors:
G Aridoss; S Balasubramanian; P Parthiban; S Kabilan
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2007-01-05
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  42     ISSN:  0223-5234     ISO Abbreviation:  Eur J Med Chem     Publication Date:  2007 Jun 
Date Detail:
Created Date:  2007-06-01     Completed Date:  2007-08-30     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  France    
Other Details:
Languages:  eng     Pagination:  851-60     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Annamalai University, Annamalainagar-608 002, Tamil Nadu, India.
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MeSH Terms
Descriptor/Qualifier:
Anti-Infective Agents / chemical synthesis,  chemistry*,  pharmacology*
Bacteria / drug effects
Fungi / drug effects
Molecular Structure
Morpholines / chemical synthesis,  chemistry*,  pharmacology*
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Anti-Infective Agents; 0/Morpholines

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