Synthesis of five-membered styryllactone derivatives and their cytotoxicity against jurkat-t leukemia cell line / Suraya Zulkepli

• Main Author: Zulkepli, Suraya
• Format: Thesis
• Language: English
• Published: 2013
• Subjects: Pharmaceutical technology
• Online Access: https://ir.uitm.edu.my/id/eprint/15576/1/TM_SURAYA%20ZULKEPLI%20PH%2013_5.PDF; https://ir.uitm.edu.my/id/eprint/15576/

Fourteen five-membered styryllactone derivatives were conveniently synthesized in two steps via Swem oxidation and Wittig olefination, as the key reactions.Microwave-assisted synthesis of several phosphonium salts was achieved in good to excellent yields. Five-membered lactone aldehydes were synthesized through Swem oxidation. These syntheses were accomplished by treatment of unstable aldehydes with various substituted phosphonium ylides through Wittig reaction and led to (E)- and (Z)-five-membered styryllactone derivatives in moderate yield. These new styryllactones exhibited moderate cytotoxicity against Jurkat-T leukemia cell lines.Compounds (Z)- 183a, (Zi)-183b and (Z)-183g (IC50 = 60 |j.M) were found to be the most active. A structure-activity relationship study (SAR) indicates that steric effectsof some substituents on the aromatic ring lead to reduce the cytotoxicity of styryllactone derivatives/analogues.