Cyclohexenones Through Regioselective Addition of 1,3-Dicarbonyl Compounds to Terpenoid-Like Bischalcones

Synthesis of New C-C Linked Bichalcones and Their Antimicrobial and Antioxidant Activities

“…[3] In the literature, it has been stated that some synthetic bichalcone analogs cause apoptosis in 4 human cancer cell lines [11] and ionone-based terpenoid-like bichalcones exhibit antibacterial activities against human pathogenic microbes. [12] The synthesis of a number of novel bichalcones has been performed, and their in vitro antiplasmodial activities against the erythrocytic stages of Plasmodium falciparum have been assessed. Some bichalcones displayed significant antiplasmodial activity (Chloroquine-sensitive Pf3D7 IC50 (mM): 2.0, 1.5, and 2.5, respectively).…”

“…[11,13,19,20] The in vitro antiplasmodial activities of a series of bichalcones were reported against the erythrocytic stages of Plasmodium falciparum, and some of them displayed remarkable antiplasmodial activity sensitive to Pf3D7 with IC50 values of 1.5-2.5 mM. [12] The isolation of Rhuschalcones II-VI from the root bark of Rhus pyroides was mentioned, and their cytotoxic activity against the HT29 and HCT-116 colon tumor cell lines was reported. [10] Therefore, concerning the pharmacological significance of bichalcones, we wanted to synthesize a novel series of methoxy-substituted bichalcones with identical substitutions at various positions on the phenyl ring (A) of chalcones.…”

“…[10] Therefore, concerning the pharmacological significance of bichalcones, we wanted to synthesize a novel series of methoxy-substituted bichalcones with identical substitutions at various positions on the phenyl ring (A) of chalcones. First, we investigated the in vitro antimicrobial potencies of the synthesized bichalcones (10)(11)(12)(13)(14)(15)(16)(17)(18) against Gram-positive and Gram-negative bacteria and yeast and then determined the antioxidant activity of all the synthesized compounds (10)(11)(12)(13)(14)(15)(16)(17)(18) with DPPH and FRAP methods.…”

Claisen–Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)‐2‐oxo‐N,4,6‐triarylcyclohex‐3‐enecarboxamide derivatives with different substituents in H2O/EtOH

“…When enolates or enamines react with α,β‐unsaturated systems several new chiral centers can be generated and it is very useful to be able to carry out such reactions with good, predictable stereochemical control. Michael addition reaction of 1,3‐dicarbonyl compounds such as acetoacetic esters to chalcones leads to the synthesis of cyclohexenone derivatives, which become interesting intermediates for the synthesis of a variety of heterocyclic systems with diverse biological activities …”

“…[24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40] When enolates or enamines react with α,β-unsaturated systems several new chiral centers can be generated and it is very useful to be able to carry out such reactions with good, predictable stereochemical control. Michael addition reaction of 1,3-dicarbonyl compounds such as acetoacetic esters to chalcones leads to the synthesis of cyclohexenone derivatives, [41][42][43][44][45][46] which become interesting intermediates for the synthesis of a variety of heterocyclic systems with diverse biological activities. [47][48][49][50][51][52] As noted above, the development of a clean procedure for the preparation of organic compounds is a major challenge in modern synthetic chemistry in view of the environmental, practical, and economic issues.…”