Relationships between Hydrophobicity and Algistatic Activity of 5‐Aryl‐3H‐[1,3,4]oxadiazole‐2‐thiones

T. Schelenz, J. Klunker, T. Bernhardt, W. Schäfer, J. Dost
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引用次数: 2

Abstract

A series of 10 acidic 5-aryl-3H-[1,3,4]oxadiazole-2-thiones was synthesized and characterized with regard to hydrophobic and algistatic properties. Apparent octan-1-ol/water (buffer pH=7.41) partition coefficients (logPapp) were determined by the shake-flask method and used to calculate the partition coefficients of the un-ionized molecules (logPu) on the basis of known pKa values. Relationships between both sets of logP and hydrophobic substituent constants are reported. Biological activity parameters (logA) were derived from growth tests using autotrophic Chlorella vulgaris cultures. The obtained data sets of logA and logP were used in QSAR studies. In this way it could be shown that the algistatic activity of meta- and para-substituted 5-aryl-3H-[1,3,4]-oxadiazole-2-thiones strongly correlates with logPapp, but slightly poorer with logPu. The results are discussed and compared with analogous QSAR/QSPR found for earlier studied series of five-membered N-heterocycles (2-amino-5-aryl-[1,3,4]oxadiazoles, 4-aryl-5-alkyl-2,4-dihydro-[1,2,4]triazol-3-ones, 5-amino-1-aryl-1H-tetrazoles).
5 -芳基- 3H -[1,3,4]恶二唑- 2 -硫酮疏水性与抑藻活性的关系
合成了一系列10个酸性5-芳基- 3h -[1,3,4]恶二唑-2-硫酮,并对其疏水和抑藻性能进行了表征。用摇瓶法测定辛烷-1-醇/水(缓冲液pH=7.41)的表观分配系数logPapp,并根据已知的pKa值计算未电离分子的分配系数logPu。报道了两组logP和疏水取代基常数之间的关系。生物活性参数(logA)由自养小球藻培养物的生长试验得出。获得的logA和logP数据集用于QSAR研究。由此可见,间位和对取代的5-芳基- 3h -[1,3,4]-恶二唑-2-硫酮的抑藻活性与logPapp相关性强,与logPu相关性稍差。并与先前研究的五元n -杂环(2-氨基-5-芳基-[1,3,4]恶二唑,4-芳基-5-烷基-2,4-二氢-[1,2,4]三唑-3-酮,5-氨基-1-芳基- 1h -四唑)的类似QSAR/QSPR进行了讨论和比较。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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