Quantum Chemical Analysis of Structural and Conformational Properties of Methisazone and Prototropic Tautomerism of Isatin

O. Bolsunova, O. Brovarets’, D. Hovorun, L. Zaika, A. Potopalsky
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引用次数: 1

Abstract

The conformational diversity of methisazone and prototropic molecular tautomerism of isatin were investigated by means of ab initio calculations at the MP2/6-311++G(2df,pd)//DFT B3LYP/6-311++G(d,p) level of theory. A comprehensive conformational, energetical and polar analysis of the methisazone (1-methyl-1H-indole-2,3-dione 3-thiosemicarbazone), a thiosemicarbazone, was provided. We established that flexibility of the thiosemicarbazone group causes conformational diversity of methisazone molecule. Structural, energetical and electron-topological characteristics of specific intramolecular contacts in methisazone conformers were analyzed. In general, two types of H-bonds (NH…O, CH…N), one type of dihydrogen bond (CH…HN) and three types of van der Waals contacts (N…N, N…O, C…O) were detected by performing electron density topological analysis for all 11 conformers of methisazone. A wide range of biological activity of izatizon based on conformational capacity of methisazone molecule, the main constituent part of this drug, was shortly discussed. Five molecular prototropic tautomers of isatin (1H-indole-2,3-dione) – one diketo and four enol tautomeric forms - were indicated. All five isomers have relative Gibbs free energies within a wide range of ~40 kcal∙mol−1 at physiological temperature. The possible biochemical role of tautomeric forms of isatin was briefly discussed
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甲巯咪唑酮结构和构象性质的量子化学分析及Isatin的原向异变异构性
在MP2/6-311++G(2df,pd)//DFT / B3LYP/6-311++G(d,p)理论水平上,通过从头计算研究了甲巯咪唑酮的构象多样性和isatin的原向性分子互变异构性。本文对甲巯氨基脲(1-甲基- 1h -吲哚-2,3-二酮3-硫代氨基脲)进行了全面的构象、能量和极性分析。我们确定了硫代氨基脲基团的柔韧性导致了甲基咪唑酮分子的构象多样性。分析了甲基沙酮构象中特定分子内接触的结构、能量和电子拓扑特征。总体而言,通过对所有11种构象进行电子密度拓扑分析,检测到两种类型的氢键(NH…O, CH…N),一种类型的二氢键(CH…HN)和三种类型的范德华触点(N…N, N…O, C…O)。本文简要讨论了该药物的主要成分甲基沙酮分子的构象能力对其生物活性的影响。结果表明,isatin (1h -吲哚-2,3-二酮)的五种分子原生互变异构体-一种二酮和四种烯醇互变异构体。在生理温度下,这5种异构体的相对吉布斯自由能均在~40 kcal∙mol−1的范围内。简要讨论了isatin互变异构体形式可能的生化作用
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