Synthesis of Novel Fatty Substituted 4-methyl-2HChromen-2-one via Cross Metathesis: Potential Antioxidants and Chemotherapeutic Agents

• Published in: Journal of oleo science Vol. 65; no. 12; p. 1023
• Main Authors: Yelchuri, Vyshnavi, Prasad, R B N, Karuna, Mallampalli S L, Poornachandra, Y, Kumar, Chityal Ganesh
• Format: Journal Article
• Language: English
• Published: Japan 01.12.2016
• Subjects: Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Cell Line, Tumor; Cell Proliferation - drug effects; Coumarins - chemical synthesis; Coumarins - chemistry; Coumarins - pharmacology; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Molecular Structure; Structure-Activity Relationship
• ISSN: 1347-3352

A series of novel fatty substituted 4-methyl-2H-chromen-2-one (coumarins) were synthesized by employing cross metathesis, a key step in the synthesis. The antioxidant activities of the title compounds were compared with the commercial antioxidants, namely butylated hydroxy toluene (BHT) and α-tocopherol, glycosidic and other substituted 4-methyl-2H-chromen-2-ones. Among the different 4-methyl-2H-chromen-2-ones, the glycosidic substituted 4-methyl-2H-chromen-2-ones was excellent, while those with aliphatic fatty acid chain and hydroxyl substitutents were good. Among the substituted 4-methyl-2H-chromen-2-ones, glycosidic, hydroxyl and cyano containing 4-methyl-2H-chromen-2-ones exhibited good, while fatty substituted exhibited moderate anticancer activities against the four different cancer cell lines tested, namely DU145 (Prostate carcinoma cancer cell), HepG2 (Hepato cellular carcinoma cancer cell), SKOV3 (Ovarian cancer cell) and MDA-MB 231 (Human breast cancer cell). The study reveals that these substituted coumarins can be potential candidates in a number of food and pharmaceutical formulations.