Design, Synthesis, Antibacterial, and Antifungal Evaluation of a New Series of Quinazoline - Thiazole and/or Quinazoline - Triazole Hybrids as Bioactive Heterocycles.

Autor: El-Shahat M; Photochemistry Department, Chemical Industries Research Institute, National Research Centre, Scopus affiliation ID 60014618, 33 EL Buhouth St., Dokki, Giza, 12622, Egypt., Tawfek N; Photochemistry Department, Chemical Industries Research Institute, National Research Centre, Scopus affiliation ID 60014618, 33 EL Buhouth St., Dokki, Giza, 12622, Egypt., El-Sofany WI; Photochemistry Department, Chemical Industries Research Institute, National Research Centre, Scopus affiliation ID 60014618, 33 EL Buhouth St., Dokki, Giza, 12622, Egypt.
Jazyk: angličtina
Zdroj: Chemistry & biodiversity [Chem Biodivers] 2024 Sep 12, pp. e202402042. Date of Electronic Publication: 2024 Sep 12.
DOI: 10.1002/cbdv.202402042
Abstrakt: Herein, a one-pot reaction between cyclohexanone, thiourea, and 2,5-dimethoxybenzaldehyde allowed to prepare hexahydroquinazoline-2(1H)-thione4 firstly, which followed by reacting with hydrazine hydrate to produce the corresponding 2-hydrazinylhexahydroquinazoline 6. Interesting analogs of thiazolo[3,2-a]quinazoline 713 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 bromo cyanoacetate, 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. Numerous spectroscopy tests, including FT-IR, NMR ( 1 H & 13 C), and MS spectrum, proved all the newly produced analogs. 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 andGriseofulvin. 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.
(© 2024 Wiley-VHCA AG, Zurich, Switzerland.)
Databáze: MEDLINE
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