Synthesis of 4′‐Hydroxy‐3′‐piperidinomethylchalcone Derivatives and Their Cytotoxicity Against PC‐3 Cell Lines

Abstract

A new series of mono Mannich bases of 4'-hydroxychalcones 2a-e carrying a variety of aryl groups was synthesized and the in vitro cytotoxic activities of the new compounds were screened against PC-3 cell lines. Bioactivities of 2a-e, which are reported for the first time in this study, were compared against their precursor 4'-hydroxychalcones 1a-e. Compound 2b was found to be the most potent (IC(50 )= 3.7 microM) among the compounds synthesized. In addition, the compounds 1a-c and 2d showed moderate cytotoxicity. Incorporation of the 3'-piperidinomethyl group in 1b and 1d raised the potency by 1.68 and 2.19 times respectively and, therefore, seemed to be a noteworthy molecular modification. Correlations were noted between cytotoxicity and one or more physiochemical constants of the aryl ring as well as log P values for the compounds 2a-e. The significant improvement of cytotoxicity of 2b, 2d, and 2e against PC-3 cell lines compared with their chalcone precursors suggests that the incorporation of a piperidinomethyl group is a useful molecular modification and further development of these compounds as candidate cytotoxic agents may be warranted.

Synthesis, structural characterization and anti-carcinogenic activity of new cyclotriphosphazenes containing dioxybiphenyl and chalcone groups

“…Because of the ketovinylenic group in chalcones and their analogs, they exhibit numerous physical and biological properties, for instance optical and fluorescence properties [30,31], dielectric properties [32,33], antioxidant and soybean lipoxygenase inhibitory activity [34], antimicrobial activity [35], Anti-HIV activity [36], antibacterial activity [37], anti-inflammatory [38] and anti-cancer activities [39][40][41][42][43][44].…”

“…The chalcone-phosphazene compounds (2e, 2f and 2g) bearing a fluorine atom exhibited better activity than other the chalcone-phosphazene compounds. In general, chalcone derivatives exhibit anti-cancer activity [39][40][41][42][43][44]. But, there are no studies about anti-cancer properties of chalcone-cyclophosphazene compounds.…”

Study of Reactions of Two Mannich Bases Derived of 4’-Hydroxychalcones with Glutathione by RP‑TLC, RP‑HPLC and RP‑HPLC‑ESI‑MS Analysis

“…18,19 Recent literature has shown phenolic Mannich bases derived from chalcones analogues to have remarkable cytotoxic potencies towards cancer cell lines. [20][21][22][23][24] However, the exact mechanism by which chalcone compounds and derivatives exert their cytotoxic effects in cancer cells remains unclear. In order to investigate how GSH-reactivity is affected by Mannich-type modification of 4'-hydroxychalcones, bis Mannich derivatives (3 and 4) of 4'-hydroxychalcones 1 and 2 have been synthesized.…”

Coumarin derivatives: Synthesis and cation binding properties

“…Mannich bases can display varied biological activities such as antimicrobial [1][2][3][4][5] , cytotoxic [6][7][8][9][10][11][12][13] , anticancer 14,15 , anti-inflammatory 16,17 and anticonvulsant 18,19 and DNA topoisomerase properties 20,21 . In this work, novel aminomethylcoumarin derivatives have been synthesized.…”