Document Detail

MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 4: Addressing the problem of poor stability due to photoisomerization of an acrylic acid moiety.
MedLine Citation:
PMID:  15109639     Owner:  NLM     Status:  MEDLINE    
Exchange of the ethylene tether in a series of pyridopyrimidine-based MexAB-OprM specific efflux pump inhibitors to an amide bond stabilized the olefin of the acrylic acid moiety, preventing facile photoisomerization to the Z-isomer. Furthermore, the activity was drastically improved in the amide tether variants, providing extremely potent acrylic acid and vinyl tetrazole analogues.
Kiyoshi Nakayama; Noriko Kuru; Masami Ohtsuka; Yoshihiro Yokomizo; Atsunobu Sakamoto; Haruko Kawato; Ken-ichi Yoshida; Toshiharu Ohta; Kazuki Hoshino; Katsuya Akimoto; Junko Itoh; Hiroko Ishida; Aesop Cho; Monica H Palme; Jason Z Zhang; Ving J Lee; William J Watkins
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  14     ISSN:  0960-894X     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2004 May 
Date Detail:
Created Date:  2004-04-27     Completed Date:  2004-12-22     Revised Date:  2005-11-17    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  2493-7     Citation Subset:  IM    
Daiichi Pharmaceutical Co., Ltd, 1-16-13, Kitakasai, Edogawa, Tokyo 134-8630, Japan.
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MeSH Terms
Acrylates / pharmacology
Bacterial Outer Membrane Proteins / antagonists & inhibitors*
Drug Resistance, Bacterial / drug effects*
Drug Stability
Membrane Transport Modulators*
Membrane Transport Proteins / antagonists & inhibitors*
Microbial Sensitivity Tests
Pseudomonas aeruginosa / drug effects*
Pyrimidines / chemical synthesis,  pharmacology
Structure-Activity Relationship
Reg. No./Substance:
0/Acrylates; 0/Bacterial Outer Membrane Proteins; 0/Membrane Transport Modulators; 0/Membrane Transport Proteins; 0/MexA protein, Pseudomonas aeruginosa; 0/MexB protein, Pseudomonas aeruginosa; 0/Pyrimidines; 79-10-7/acrylic acid

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