Synthesis of curcumin analogues as potential antioxidant, cancer chemopreventive agents.
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.
Youssef
Khairia M
KM
Department of Medicinal Chemistry, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia. Khairia_m@yahoo.com
El-Sherbeny
Magda A
MA
El-Shafie
Faiza S
FS
Farag
Hassan A
HA
Al-Deeb
Omar A
OA
Awadalla
Sit Albanat A
SA
D000255:Adenosine Triphosphate; D000466:Alkadienes / Q000138:chemical synthesis / Q000633:toxicity; D000818:Animals; D016588:Anticarcinogenic Agents / Q000138:chemical synthesis*; D000975:Antioxidants / Q000138:chemical synthesis*; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D003474:Curcumin / Q000031:analogs & derivatives* / Q000737:chemistry; D003508:Cycloheptanes / Q000138:chemical synthesis / Q000633:toxicity; D003510:Cyclohexanes / Q000138:chemical synthesis / Q000633:toxicity; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000633:toxicity; D005260:Female; D005544:Forecasting; D016166:Free Radical Scavengers / Q000138:chemical synthesis; D005609:Free Radicals / Q000737:chemistry; D006801:Humans; D008163:Luminescent Measurements; D008297:Male; D015394:Molecular Structure; D009504:Neutrophils / Q000166:cytology / Q000187:drug effects; D010881:Piperidones / Q000138:chemical synthesis / Q000633:toxicity
D000466:Alkadienes; D016588:Anticarcinogenic Agents; D000975:Antioxidants; D003508:Cycloheptanes; D003510:Cyclohexanes; D003517:Cyclopentanes; D016166:Free Radical Scavengers; D005609:Free Radicals; D010881:Piperidones; D000255:Adenosine Triphosphate; D003474:Curcumin; C000363:cycloheptanone