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Complete chemical shift assignment and molecular modeling studies of two chromene derivatives as potential leads for new anticancer drugs
Journal of Biomolecular Structure and Dynamics ( IF 2.7 ) Pub Date : 2020-07-13 , DOI: 10.1080/07391102.2020.1790419
Priscila Ivo Rubim de Santana 1 , Denise Cristian Ferreira Neto 1 , Arlan da Silva Goncalves 2, 3 , Joyce Sobreiro Francisco Diz de Almeida 2 , Tanos Celmar Costa França 2, 3 , José Daniel Figueroa-Villar 1
Affiliation  

Abstract

The compounds 7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one (5) and 5-[-7-chloro-2,4-dioxo-1H, 2H, 3H, 4H, 5H-chromeno[2,3-d]pyrimidin-5-yl)]-1,3-diazinane-2,4,6-trione (7), were synthesized from dimedone and barbituric acid and had their three-dimensional structures and precise chemical shifts assignments obtained by Nuclear Magnetic Resonance (NMR) from 1H, 13C, APT, COSY, HSQC, and HMBC spectra. Additional HOMO-LUMO DFT calculations corroborated the NMR results and pointed to the most stable stereoisomers of each compound. Besides, further docking and molecular dynamic studies suggest that the stereoisomers (9S)-7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one, and 5-[(5S)-7-chloro-2,4-dioxo-1H, 2H, 3H, 4H, 5H-chromeno[2,3-d]pyrimidin-5-yl)]-1,3-diazinane-2,4,6-trione of these compounds may act as DNA intercalators and qualify as potential leads for the development of new anticancer drugs.

Communicated by Ramaswamy H. Sarma



中文翻译:

两种色烯衍生物作为新型抗癌药物的潜在先导物的完整化学位移分配和分子建模研究

摘要

化合物7-氯-9-(2-羟基-4,4-二甲基-6-氧代环己-1-烯-1-基)-3,3-二甲基-2,3,4,9-四氢-1H- xanthen-1-one ( 5 ) 和 5-[-7-chloro-2,4-dioxo-1H, 2H, 3H, 4H, 5H-chromeno[2,3-d]pyrimidin-5-yl)]-1 ,3-diazinane-2,4,6-trione ( 7 ) 由二甲酮和巴比妥酸合成,并通过核磁共振 (NMR) 从1 H, 13获得了它们的三维结构和精确的化学位移分配C、APT、COSY、HSQC 和 HMBC 光谱。额外的 HOMO-LUMO DFT 计算证实了 NMR 结果,并指出了每种化合物最稳定的立体异构体。此外,进一步的对接和分子动力学研究表明立体异构体 (9S)-7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-二甲基-2,3,4,9-四氢-1H-xanthen-1-one 和 5-[(5S)-7-chloro-2,4-dioxo-1H, 2H, 3H, 4H, 5H-chromeno[这些化合物中的 2,3-d]pyrimidin-5-yl)]-1,3-diazinane-2,4,6-trione 可以作为 DNA 嵌入剂,并有资格作为开发新抗癌药物的潜在线索。

由 Ramaswamy H. Sarma 交流

更新日期:2020-07-13
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