ChemInform Abstract: Antifungal Quinazolinones from Marine-Derived Bacillus cereus and Their Preparation.

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.
Bioorganic & medicinal chemistry letters (Impact Factor: 2.42). 07/2011; 21(13):4005-7. DOI: 10.1016/j.bmcl.2011.05.002
Source: PubMed


Two new quinazolinones alkaloids, R(+)-2-(heptan-3-yl)quinazolin-4(3H)-one (1) and (2R,3'R)+(2S,3'R)-2-(heptan-3-yl)-2,3-dihydroquinazolin-4(1H)-one (2) (a pair of epimers), as well as seven known analogues, 2-methylquinazolin-4(3H)-one (3), 2-benzylquinazolin-4(3H)-one (4), cyclo-(Pro-Ile), cyclo-(Pro-Leu), cyclo-(Pro-Val), cyclo-(Pro-Phe), and cyclo-(Tyr-Pro) were isolated from the n-butyl alcohol extract of the marine-derived bacterium Bacillus cereus 041381. The new compounds were identified by spectroscopic analysis and chemical synthesis. Four optical isomers 5-8 were also synthesized. Compounds 1-8 all showed moderate antifungal activity against Candida albicans with MIC values of 1.3-15.6 μM. Compound 5 exhibits the most powerful antifungal activity, which may reveal that S-configuration and 2,3-double bond were necessary for antifungal activity, and the racemization at C-2 and C-3' reduced the antifungal activity.

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    • "The six known compounds were identified as quinazolin-4(3H)- one (2) (Chang et al., 2003), 2-methylquinazolin-4(3H)-one (3) (Chang et al., 2003), 2-(4-hydroxyphenyl) quinazolin-4(3H)-one (4) (Chen et al., 2008), 2-acetamido benzamide (Phay et al., 1996), 1H-indole-3carbaldehyde (Wang et al., 2013), and 2-phenylace- tamide (Amal et al., 2007), respectively, by analysis of their spectroscopic data, which were identical in all respects to those appeared in the literature data. Although many quinazolinone derivatives, including compounds 3 and 4, were reported to have various pharmaceutical and biological properties (Khan et al., 2014; Kumar et al., 2011b; Xu et al., 2011), the isolated quinazolinone 1 and also compound 5 have never been reported for their biological activities. Therefore, these two compounds were subjected to assay for antifungal against Candida albicans, antibacterial activity against Bacillus cereus and Staphylococcus aureus, and cytotoxic activities against KB, MCF-7, NCI-H187, and Vero cells. "
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    ABSTRACT: Four quinazolinones, new naturally occurring 1 and three known derivatives 2-4, along with previously synthesized 4-phenylbut-3-enamide (5) and three known compounds, 2-acetamido benzamide, 1H-indole-3-carbaldehyde, and 2-phenylacetamide, were isolated from an actinomycete, Streptomyces sp. BCC 21795. The structures were elucidated based on the analysis of NMR spectroscopic and mass spectrometric data. Compound 1 exhibited strong cytotoxic activity to Vero cells with IC50 3.30 μg/mL. © 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
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