Document Detail

Synthesis, antifungal activity and CoMFA analysis of novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives.
MedLine Citation:
PMID:  17618711     Owner:  NLM     Status:  MEDLINE    
In order to search novel agrochemicals with higher antifungal activity, a series of new 1,2,4-triazolo[1,5-a]pyrimidine derivatives bearing 1,3,4-oxadiazole moieties were designed and synthesized. Their antifungal activities against Rhizoctonia solani were evaluated in vitro. By determining the EC(50) values of all the newly synthesized compounds and 10 formerly synthesized compounds, compound 8r, 2-((5-(sec-butylthio)-1,3,4-oxadiazol-2-yl)-methylthio)-5-dimethyl-1,2,4-triazolo-[1,5-a]pyrimidine, was found to display the highest antifungal activity (EC(50)=6.57 microg mL(-1)). Based on the quantitative structure-activity relationships analyses, 2-(1-(5-(sec-butylthio)-1,3,4-oxadiazol-2-yl)ethylthio)-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine (9j) was designed and synthesized, which was found to display much higher activity (EC(50)=3.34 microg mL(-1)) than compound 8r and the control. To further explore the comprehensive structure-activity relationships, a 3D-QSAR analysis using the method of comparative molecular field analysis (CoMFA) was performed and a statistically reliable model with good predictive power (r(2)=0.929, q(2)=0.588) was achieved on the basis of the common substructure-based alignment. According to the CoMFA model, the structure-antifungal activity relationship was explained reasonably.
Qiong Chen; Xiao-Lei Zhu; Li-Li Jiang; Zu-Ming Liu; Guang-Fu Yang
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2007-05-27
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  43     ISSN:  0223-5234     ISO Abbreviation:  Eur J Med Chem     Publication Date:  2008 Mar 
Date Detail:
Created Date:  2008-03-10     Completed Date:  2008-06-26     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  France    
Other Details:
Languages:  eng     Pagination:  595-603     Citation Subset:  IM    
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR China.
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MeSH Terms
Antifungal Agents / chemical synthesis*,  chemistry,  pharmacology*
Drug Design
Inhibitory Concentration 50
Pyrimidines / chemical synthesis*,  chemistry,  pharmacology*
Rhizoctonia / drug effects
Structure-Activity Relationship
Triazoles / chemical synthesis*,  chemistry,  pharmacology*
Reg. No./Substance:
0/Antifungal Agents; 0/Pyrimidines; 0/Triazoles

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