N-置換およびN,N-二置換2,4-dihydroxythiobenzamide類の合成, 抗菌活性および構造活性相関 Synthesis, antifungal activity and SAR of N-substituted and N,N-disubstituted 2,4-dihydroxythiobenzamides
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Sulfinyl-bis-(2,4-dihydroxythiobenzoyl)と1級あるいは2級アミンとの反応により2,4-dihydroxythiobenzamideのN-置換およびN,N-二置換体を合成し, 5種類の植物病原糸状菌に対する生育阻害活性をin vitroで測定した.これらの化合物の活性は, 主に, 疎水性に依存しており, 菌生育阻害活性は, 疎水性(1-オクタノール/水系分配係数の計算値および逆相液体クロマトグラフィーの保持時間より計算されたlog k_w)の増大とともに高くなるが, 疎水性がある程度の値を超えると減少していくという関係が見いだされた.また, チオアミド結合の電子的性質に対するN-置換の影響を, ^1H NMR, MSおよびIRスペクトルに基づいて解析した.
N-Substituted and N,N-disubstituted 2,4-dihydroxythiobenzamides were synthesized and their fungistatic properties were examined. The compounds were prepared by reacting sulfinyl-bis-(2,4-dihydroxythiobenzoyl) with primary or secondary amines. The activities of the derivatives against five phytopathogenic fungi were measured in vitro. The growth-inhibitory activity of these compounds depends mainly on their lipophilicity. Parabolic relationships between growth-inhibitory activity and lipophilicity (calculated n-octanol-water partition coefficient and log k_w from reversed phase chromatography) were found. The influence of the type of N-substitution on the character of the thioamide bond was analyzed based on ^1H NMR, MS and IR spectra.