Antibacterial activities against Ralstonia solanacearum and Xanthomonas oryzae pv. oryzae of 6-chloro-4-(4-substituted piperazinyl)quinazoline derivatives. Issue 4 (15th February 2020)

• Record Type: Journal Article
• Authors: Shao, Wu-Bin; Zheng, Yu-Tao; Liu, Jia-Min; Fu, Yi-Hong; Qi, Pu-Ying; Zhou, Xiang; Wu, Zhi-Bing; Wang, Pei-Yi; Yang, Song
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 30:Issue 4(2020)
• Publication Date: 2020-02-15
• Subjects: Quinazoline -- Synthesis -- Antibacterial -- 3D-QSAR -- Morphological studies; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2019.126912
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Highlights: Twenty-eight simple 6-chloro-4-(4-substituted piperazinyl)quinazoline derivatives were constructed. Most of the title molecules showed significant antibacterial activities. Compound 5g exerted the strongest activity against Ralstonia solanacearum with EC50 of 2.72 µg/mL. A good predictive 3D-QSAR model was established to direct the future structural modification. Abstract: In this letter, a variety of simple 6-chloro-4-(4-substituted piperazinyl)quinazoline derivatives was prepared. Preliminary bioassays revealed that these compounds showed good antibacterial activities toward phytopathogens Ralstonia solanacearum and Xanthomonas oryzae pv. oryzae ( Xoo ). Among these derivatives, compounds 5a, 5d, 5e, 5f, 5p, 5q, 6b, and 6d exhibited potent inhibition effects against R. solanacearum with EC50 within 4.60–9.94 µg/mL, especially, compound 5g exerted the strongest activity with EC50 of 2.72 µg/mL; compound 6b possessed the best inhibitory activity toward Xoo with EC50 of 8.46 µg/mL. Subsequently, a good predictive three-dimensional quantitative structure–activity relationship (3D-QSAR) model was constructed via CoMFA to direct the future structural modification and optimization. Furthermore, the pathogens' topological studies were performed to explore the possible antibacterial mechanism. Given their simple frameworks and facile synthesis, title compounds can serve as the potential antibacterial leads.