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Synthesis, Antibacterial Activities, and 3 D ‐ QSAR of Sulfone Derivatives Containing 1, 3, 4‐Oxadiazole Moiety
Author(s) -
Li Pei,
Yin Juan,
Xu Weiming,
Wu Jian,
He Ming,
Hu Deyu,
Yang Song,
Song Baoan
Publication year - 2013
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12181
Subject(s) - moiety , chemistry , oxadiazole , sulfone , quantitative structure–activity relationship , stereochemistry , combinatorial chemistry , organic chemistry
A series of sulfone derivatives containing 1, 3, 4‐oxadiazole moiety were prepared and evaluated for their antibacterial activities by the turbidimeter test. Most compounds inhibited growth of R alstonia solanacearum ( R. solanacearum ) from tomato and tobacco bacterial wilt with high potency, among which compounds 5a and 5b exhibited the most potent inhibition against R. solanacearum from tomato and tobacco bacterial wilts with EC 50 values of 19.77 and 8.29 μ g/mL, respectively. Our results also demonstrated that 5a, 5b , and a number of other compounds were more potent than commercial bactericides Kocide 3000 and Thiodiazole Copper, which inhibited R. solanacearum from tomato bacterial wilt with EC 50 values of 93.59 and 99.80 μ g/mL and tobacco bacterial wilt with EC 50 values of 45.91 and 216.70 μ g/mL, respectively. The structure–activity relationship (SAR) of compounds was studied using three‐dimensional quantitative structure–activity relationship (3 D ‐ QSAR ) models created by comparative molecular field analysis ( C o MFA ) and comparative molecular similarity index analysis ( C o MSIA ) based on compound bioactivities against tomato and tobacco bacterial wilts. The 3 D ‐ QSAR models effectively predicted the correlation between inhibitory activity and steric–electrostatic properties of compounds.