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.
"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. "
[Show abstract][Hide abstract] ABSTRACT: Novel thiazole, pyrimidine and benzylidene derivatives derived from quinazoline scaffold have been synthesized. The antitumor evaluation of the newly synthesized products against three cancer cell lines namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460), and CNS cancer (SF-268) showed that the benzylidene–quinazoline derivative 12a showed remarkable activity against all three cell lines. The thiazolo-quinazoline derivative 10 showed greater activity than the control against breast adenocarcinoma (MCF-7) with a concentration of 0.01 μM. Moreover, the antileishmanial activity of the newly synthesized products tested on Leishmania donovani amastigotes showed that compounds 4, 14, and 18 had very promising activity.
Medicinal Chemistry Research 05/2012; 22(5). DOI:10.1007/s00044-012-0213-9 · 1.40 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: Diketopiperazines (DKPs) are a class of secondary metabolites that result from peptide bonds between two amino acids to form a lactam. Due to their rigid structure, chiral nature, and varied side chains, DKPs have been of research interest for their diverse bioactivities. However, little is known about whether DPKs stimulate the release of cytokine and chemokines in macrophage cells. The present aim was to study the effect of DKPs firstly isolated from sponge Callyspongia sp. on the release of several cytokines in murine macrophage-like cell line J774A.1 after stimulation in vitro, and their potential structure-activity relationship of five natural DKPs on four representative cytokines, interferon-γ (IFN-γ), pro-inflammatory (tumor necrosis factor, TNF-α), anti-inflammatory cytokine (interleukin-10, IL-10), and chemokine (monocyte chemoattractant protein-1, MCP-1). Results suggested that these five DKPs, especially DKP 1 bearing 3-hydroxyl-l-proline (l-Hyp), might be useful as a promising macrophage cytokines stimulator.
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