Synthesis of Curcumin Analogues as Potential Antioxidant, Cancer Chemopreventive Agents

Abstract

New series of 3, 5-bis(substituted benzylidene)-4-piperidones, 2, 7-bis(substituted benzylidene)cycloheptanones, 1, 5-bis(substituted phenyl)-1, 4-pentadien-3-ones, 1, 7-bis(substituted phenyl)-1, 6-heptadien-3, 5-diones, 1, 1-bis(substituted cinnamoyl)-cyclopentanes, and 1, 1-bis(substituted cinnamoyl)cyclohexanes have been synthesized and tested for their antioxidant activity. Among the tested compounds, compounds II(4), II(9) II(10), II(11), V(1), and V(4) exhibited higher free radical scavenger activity with % inhibition values of 90.71, 91.24, 96.91, 94.26, 99.23, and 99.85%, respectively. Moreover, compound V(1) is the safest member toward peripheral multinuclear neutrophils (PMNs) with a % viability value of 91%. Detailed synthesis, spectroscopic, and biological data are reported.

Synthesis and biological analysis of new curcumin analogues bearing an enhanced potential for the medicinal treatment of cancer

“…However, it has some short points, including its low bioavailability claimed in vivo. These characters of curcumin are encouraging investigators to modify it into more aggressive forms to induce tumor suppression (23,26,27). Our strategy is to develop the new curcumin analogues systemically.…”

1,5-Diaryl-3-oxo-1,4-pentadienes: A Case for Antineoplastics with Multiple Targets

“…The series of compounds 29 and 30 were prepared as antioxidants and their relative ability to scavenge free radicals was determined towards diphenylpicrylhydrazyl [58]. The pseudo first order rate constants (K min −1 × 10 −2 ) were determined from which the following correlations between structure and antioxidant properties were noted.…”

“…Series 55 were prepared as candidate antioxidants and shown to possess radical-scavenging properties as determined towards diphenylpicrylhydrazyl [58]. Other studies with compounds related to 55 displayed good antioxidant properties and maximum potencies are displayed by compounds possessing two small substituents ortho to the aryl hydroxy group [75].…”

Copper‐Mediated Selective Oxidation of a CH Bond

“…[3][4][5] A number of synthetic routes to HDB starting from 2,4,6-trimethylphenol (TMP) involving stoichiometric amounts or an excess of oxidant are known. [6][7][8][9][10] So far, the only catalytic oxidation of TMP to HDB was achieved by Takehira and co-workers.…”