Su, Shijun; Chen, Mei; Li, Qin; Wang, Yihui; Chen, Shuai; Sun, Nan; Xie, Chengwei; Huai, Ziyou; Huang, Yinjiu; Xue, Wei published the artcile< Novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments: Design, synthesis and bioactivity>, Reference of 611-19-8, the main research area is quinazolinyl pentadieneone oxime ether preparation diastereoselective antitumor SAR drug; Anticancer; Oxime ether; Penta-1, 4-diene-3-one; Quinazoline; SMMC-7721 cells.
A series of novel penta-1,4-diene-3-one derivatives I [R = H, [(2,4-dichlorophenyl)methyl]oxidanyl, [(2-chlorophenyl)methyl]oxidanyl, [(4-chlorophenyl)methyl]oxidanyl, [(2-fluorophenyl)methyl]oxidanyl; R1 = thiophen-2-yl, pyridin-2-yl; R2 = H, [(2-fluorophenyl)methyl]oxidanyl, [(2,4-dichlorophenyl)methyl]oxidanyl, [(3-methylphenyl)methyl]oxidanyl, etc.; R3 = H, 6-Cl, 8-Me] containing quinazoline and oxime ether moieties were designed and synthesized. Their anticancer activities were evaluated by MTT assay, and the results showed that most compounds exhibited extremely inhibitory effects against hepatoma SMMC-7721 cells. In particular, compounds I [R = R3 = H; R1 = pyridin-2-yl; R2 = [(3-methylphenyl)methyl]oxidanyl] (II) and I [R = H; R1 = pyridin-2-yl; R2 = [(4-chlorophenyl)methyl]oxidanyl; R3 = 6-Cl] (III) displayed the more potent inhibitory activity with IC50 values of 0.64 and 0.63μM, which were better than that of gemcitabine (1.40μM). Further mechanism studies indicated that compounds II, III, I [R = [(2,4-dichlorophenyl)methyl]oxidanyl; R1 = pyridin-2-yl; R2 = R3 = H] and I [R = [(2,4-dichlorophenyl)methyl]oxidanyl; R1 = pyridin-2-yl; R2 = H; R3 = 6-Cl] could control the migration of SMMC-7721 cells effectively, and inhibit the proliferation of cancer cells by inhibiting the DNA replication. Western-blot results showed that compounds II and III induced irreversible apoptosis of SMMC-7721 cells by regulating the expression level of apoptose-related proteins. Those studies demonstrated that the penta-1,4-diene-3-one derivatives I containing quinazoline and oxime ether fragments merited further research as potential anticancer agents.
Bioorganic & Medicinal Chemistry published new progress about Antitumor agents. 611-19-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C7H6Cl2, Reference of 611-19-8.
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Chlorides – an overview | ScienceDirect Topics