Abstract

(E)-4,6-dibromo-2-[(2-chlorophenylimino)methyl]-3-methoxyphenol (I) and (E)-4,6-dibromo-2-[(2,5-difluorophenylimino)methyl]-3-methoxyphenol (II) Schiff base compounds were synthesized and characterized by using experimental XRD, FT-IR, UV-Vis. spectroscopic methods and computational methods. Geometry optimizations were done by using Gaussian type orbitals in Gaussian 09 W and Slater type orbitals in ADF2009 software. Spectroscopic studies show that the compounds prefer enol form in both solid and solvent. Scan calculations revealed that the reason for the enol form preference and the energy for prototropic tautomerism. From the biological activity estimations, it was determined that the compounds could be a Monoamine Oxidase Type B inhibitor, and comparative in-silico molecular docking studies with reverse docking of human monoamine oxidase type B protein were performed. Theoretical NLO calculations show that the second-order polarizability values of I and II were over 18 and 13 times that of the urea. Conceptual DFT studies were carried out to determine the reactivity descriptors of the molecules.

摘要

(E)-4,6-二溴-2-[(2-氯苯基亚氨基)甲基]-3-甲氧基苯酚( I )和(E)-4,6-二溴-2-[(2,5-二氟苯基亚氨基)甲基] -3-甲氧基苯酚（Ⅱ) 采用实验XRD、FT-IR、UV-Vis合成和表征席夫碱化合物。光谱方法和计算方法。通过使用 Gaussian 09 W 中的 Gaussian 型轨道和 ADF2009 软件中的 Slater 型轨道进行几何优化。光谱研究表明，这些化合物在固体和溶剂中都倾向于烯醇形式。扫描计算揭示了烯醇形式偏好的原因和原质互变异构的能量。根据生物活性估计，确定这些化合物可能是 B 型单胺氧化酶抑制剂，并进行了与人单胺氧化酶 B 型蛋白反向对接的比较计算机内分子对接研究。理论 NLO 计算表明I的二阶极化率值和II分别是尿素的 18 和 13 倍。进行概念 DFT 研究以确定分子的反应性描述符。