New heterocyclic chalcones. Part 6. Synthesis and cytotoxic activities of 5- or 6-(3-aryl- 2-propenoyl)-2(3H)-benzoxazolones

Abstract

A number of chalcones bearing an oxazole cycle were synthesized by Claisen-Schmidt condensation of 5-acetyl-2(3 H )-benzoxazolone or 6-acetyl-2(3 H )-benzoxazolone and the appropriate aldehydes. The chalcones were evaluated for cytotoxic activity against several tumor cell lines -BV-173 (human B cell precursor leukemia), MCF-7 and MDA-MB-231 (human breast adenocarcinoma) using the MTT-dye reduction assay. The tested compounds exhibit concentration-dependent cytotoxic effects at micromolar concentrations. Exposure of the BV-173 tumor cell line to compound 3f results in strong monoand oligonucleosomal fragmentation of genomic DNA, as evidenced by a ' cell death detection ' ELISA kit, which unambiguously indicates that the induction of apoptosis is implicated in the cytotoxic mode of action of the tested compound.

New halogenated chalcones with cytotoxic and carbonic anhydrase inhibitory properties: 6‐(3‐Halogenated phenyl‐2‐propen‐1‐oyl)‐2(3H)‐benzoxazolones

“…As shown in Scheme 1, 2(3 H )‐benzoxazolone was acylated by Friedel–Crafts reaction. A direct acylation of the 2(3 H )‐benzoxazolone ring is regioselective and always leads to a 6‐acetyl derivative [ 62 ] in good yield and purity. Chalcones 2a , 2b , 2d – g , and 2j – l were synthesized by classical Claisen–Schmidt condensation reaction, whereas chalcones 2c , 2h , 2m , and 2n were synthesized by a microwave irradiation method.…”

“…In a very limited number of studies, some chalcones bearing 2(3 H )‐benzoxazolone with different substituents on the phenyl ring were reported with their strong cytotoxic activities. [ 3,58,61,62 ] Both the selective and strong anticancer activities of these compounds pointed out the importance of this chemical moiety in designing new chalcone compounds for possible drug candidate molecules. Thus, we chose the chalcone structure bearing the 2(3 H )‐benzoxazolone heterocycle as the main chemical skeleton for further investigation.…”

Novel Hybrid Molecules of Isoxazole Chalcone Derivatives: Synthesis and Study of in vitro Cytotoxic Activities

“…Bulky substituents (Br or OMe group) in meta position of benzylidene affect anti-proliferative effects of chalcone analogues due to interaction with biological targets [19]. Less contribution of substituents (Cl, Br, NO 2 , OH, CN, or CF 3 ) to antitumour activity was reported with chalcones containing quinazolines [20] and quinoxaline [21].…”

6-[1-Acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-yl]-2(3H)-benzoxazolone

“…All chemicals were purchased from Acros Organics (Geel, Belgium). 6-[3-(4-Methoxyphenyl)-2propenoyl]-2(3H)-benzoxazolone (1) was synthesized as described previously [6,7]. Reactions and purity of the final compound were monitored by thin-layer chromatography (TLC) on silica gel plates (Kieselgel 60 F 254 ), using ethyl acetate/cyclohexane (3:2 v/v) as eluent.…”