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Design, synthesis, in vitro cytotoxicity evaluation and structure–activity relationship of Goniothalamin analogs

Author:
Mohideen, Mazlin, Zulkepli, Suraya, Nik-Salleh, Nik-Salmah, Zulkefeli, Mohd, Weber, Jean-Frédéric Faizal Abdullah, Rahman, A. F. M. Motiur
Source:
Archives of pharmacal research 2013 v.36 no.7 pp. 812-831
ISSN:
0253-6269
Subject:
T-lymphocytes, cytotoxicity, inhibitory concentration 50, lactones, naphthalene, pyridines, structure-activity relationships
Abstract:
A series of six/five member (E/Z)-Goniothalamin analogs were synthesized from commercially available (3,4-dihydro-2H-pyran-2-yl)methanol/5-(hydroxymethyl)dihydrofuran-2(3H)-one in three steps with good to moderate overall yields and their cytotoxicity against lymphoblastic leukemic T cell line (Jurkat E6.1) have been evaluated. Among the synthesized analogs, (Z)-Goniothalamin appeared to be the most active in cytotoxicity (IC₅₀ = 12 μM). Structure–activity relationship study indicates that introducing substituent in phenyl ring or replacing phenyl ring by pyridine/naphthalene, or decreasing the ring size of lactones (from six to five member) do not increase the cytotoxicity.
Agid:
224410