Design, Synthesis, Antibacterial, and Antifungal Evaluation of a New Series of Quinazoline—Thiazole and /or Quinazoline—Triazole Hybrids as Bioactive Heterocycles
Mahmoud El-Shahat, Nashwa Tawfek, Walaa I. El-Sofany
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引用次数: 0
Abstract
Herein, a one‐pot reaction between cyclohexanone, thiourea, and 2,5‐dimethoxybenzaldehyde allowed to prepare hexahydroquinazoline‐2(1H)‐thione 4 firstly, which dollowed by reacting with hydrazine hydrate to produce the corresponding 2‐hydrazinylhexahydroquinazoline 6. Interesting analogs of thiazolo[3,2‐a]quinazoline 7‐13 where obtained when hexahydroquinazoline‐2(1H)‐thione 4 reacted with 1,2‐dibromoethane, chloroacetyl chloride, bromoacetic acid, bromoacetic acid/4‐chlorobenzaldehyde, 2‐bromopropionic acid, ethyl bromocyanoacetate, and/or bromomalononitrile; respectively. While triazolo[4,3‐a] quinazoline 14‐16 were created when 2‐hydrazinylhexahydroquinazoline 6 reacted with triethyl orthoformate, acetic anhydride, and carbon disulfide respectively. Additionally, the new analogs were examined for their antibacterial and antifungal properties against Escherichia coli, Staphylococcus aureus, and Candida albicans. It was discovered that triazolo[4,3‐a] quinazoline analogs 14‐16 have superior bacterial and fungal activity when compared to the corresponding conventional doses of Streptomycin and Griseofulvin. Towards Candida albicans; compounds 14, 15, and 16 increase activity with 1.14%, 1.15%, and 1.21%, respectively more than griseofulvin.While, for Staphylococcus aureus; compounds 14, 15, and 16 increase activity with 1.5%, 1.5%, and 1.7%, respectively more than streptomycin. Morever, for Escherichia coli; compounds 14, 15, and 16 increase activity with 1.19%, 1.21%, and 1.22%, respectively more than streptomycin. Finally, structure activity relationships show that quinazoline derivatives exhibit higher activity when fused to pyrazole ring 14–16 as compared when fused thiophene ring 7–13.
期刊介绍:
Chemistry & Biodiversity serves as a high-quality publishing forum covering a wide range of biorelevant topics for a truly international audience. This journal publishes both field-specific and interdisciplinary contributions on all aspects of biologically relevant chemistry research in the form of full-length original papers, short communications, invited reviews, and commentaries. It covers all research fields straddling the border between the chemical and biological sciences, with the ultimate goal of broadening our understanding of how nature works at a molecular level.
Since 2017, Chemistry & Biodiversity is published in an online-only format.