Abstract

In order to develop motifs with the potential applications as drugs and dyes, a series of novel quinoline–pyrimidine monoazo hybrids have been synthesized via the Biginelli reaction followed by diazo coupling. Molecular docking study of the synthesized compounds was performed against Topoisomerase IV from E. coli K-12 and CYP51 from C. albicans. The ADMET properties of the synthesized compounds were also investigated in order to understand the efficacy of drug candidates. The compounds bearing naphthol and orcinol substitutions showed excellent antifungal and antibacterial properties. The α-naphthol derivative displayed the highest binding affinity score (8.46 against Topoisomerase IV and 7.50 against CYP51) and an acceptable drug score (0.53) in toxicological and pharmacokinetics studies. The orcinol derivative showed a very good docking score but a low drug score in the ADMET study. Additionally, the dye ability of the synthesized compounds was assessed by dyeing cotton and silk fabrics. The compound containing a paracetamol moiety displayed excellent performance in terms of color and rubbing fastness and is promising for use in the textile industry for dyeing clothes.

中文翻译：

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喹啉-嘧啶单偶氮染料杂化物：合成、催化剂优化、分子对接和 ADMET 研究、生物活性和染料能力评估

摘要

为了开发具有药物和染料潜在应用的基序，通过 Biginelli 反应和重氮偶联合成了一系列新型喹啉-嘧啶单偶氮杂化物。针对大肠杆菌K-12 的拓扑异构酶 IV 和白色念珠菌的 CYP51对合成的化合物进行了分子对接研究。还研究了合成化合物的 ADMET 特性，以了解候选药物的功效。带有萘酚和苔黑酚取代基的化合物显示出优异的抗真菌和抗菌特性。α-萘酚衍生物在毒理学和药代动力学研究中显示出最高的结合亲和力评分（针对拓扑异构酶 IV 为 8.46，针对 CYP51 为 7.50）和可接受的药物评分（0.53）。苔黑酚衍生物在 ADMET 研究中显示出非常好的对接分数，但药物分数较低。此外，通过对棉和丝织物染色来评估合成化合物的染色能力。该含有扑热息痛部分的化合物在颜色和摩擦牢度方面表现出优异的性能，有望用于纺织工业的衣服染色。