Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
Regioselective synthesis of 9,10-dihydro-2,5-dimethoxyphenanthrene-1,7-diol (1) and 9,10-dihydro-2,7-dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key steps. The synthesis was successfully completed in total of 15 steps with 3.3% overall yield in case of 1 and in total of 13 steps with 9.0% overall yield in case of 2. All compounds (1-4) showed good antioxidant and anti-inflammatory activity in in vitro assays and these activities were found to be due the presence of phenolic hydroxyl groups.
Reliance Life Sciences Pvt. Ltd., Dhirubhai Ambani Life Sciences Center, Thane Belapur Road, Rabale, Navi Mumbai 400 701, India.
Yogesh
Y
Kanekar
Khalander
K
Basha
Sharad
S
Duche
Rajan
R
Gupte
Arnab
A
Kapat
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D015394:Molecular Structure; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors / Q000096:biosynthesis
D000894:Anti-Inflammatory Agents, Non-Steroidal; D000975:Antioxidants; D008070:Lipopolysaccharides; D010616:Phenanthrenes; D014409:Tumor Necrosis Factor-alpha
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