Design, structure activity relationship, cytotoxicity and evaluation of antioxidant activity of curcumin derivatives/analogues.
New fourteen 3,4-dihydropyrimidine derivatives/analogues of curcumin (2a-2n) were designed, synthesized and biologically evaluated for their cytotoxicity and antioxidant activity. Cytotoxicity effect has been evaluated against three cell lines HeLa, HCT-116 and QG-56 by MTT assay method. From SAR study, it has been revealed that particularly, compound 2e and 2j (IC50 value 12.5 μM) have shown better cytotoxicity effect against three cell lines. According to results of SAR study, it was found that 3,4-dihydropyrimidines of curcumin, 2c, 2d, 2j and 2n exhibited better antioxidant activity than curcumin. A correlation of structure and activities relationship of these compounds with respect to drug score profiles and other physico-chemical properties of drugs are described and verified experimentally. Therefore, we conclude that physico-chemical analyses may prove structural features of curcumin analogues with their promising combined cytotoxicity/antioxidant activity and it is also concluded from virtual and practical screening that the compounds were varied to possess a broad range of lipophilic character, revealed by Log P values.
School of Studies in Chemistry, Jiwaji University, Gwalior 474011, Madhya Pradesh, India; Department of Industrial Chemistry, Jiwaji University, Gwalior 474011, Madhya Pradesh, India. Electronic address: sahu.chemistry@gmail.com.
Pramod K
PK
Sahu
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000737:chemistry; D045744:Cell Line, Tumor; D003474:Curcumin / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015195:Drug Design; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D009569:Nitric Oxide / Q000737:chemistry; D010851:Picrates / Q000737:chemistry; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D010851:Picrates; D009569:Nitric Oxide; C004931:1,1-diphenyl-2-picrylhydrazyl; D003474:Curcumin
Antioxidant activity; Curcumin derivatives/analogues; Drug design; Physico-chemical analyses; Structure-activity relationship