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Potential antineoplastic dihydroxy‐fatty acids
Author(s) -
Piatak David M.,
Tang PuiFun Louisa
Publication year - 1985
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02534775
Subject(s) - chemistry , moiety , aldehyde , fatty acid , ketone , organic chemistry , ethylene glycol , biochemistry , stereochemistry , catalysis
The fatty acid aglycones of two naturally occurring glycosides, one of which is reported to possess antitumor activity, were synthesized for biological evaluation. The preparation of 3,11‐dihydroxyhexadecanoic acid and 3,12‐dihydroxyhexadecanoic acid started with the monoethyl esters of nonanedioic acid and decanedioic acid, respectively, and proceeded through the corresponding C 14 ketoesters, ketalesters, and ketalaldehydes and C 16 ketalhydroxyesters and dihydroxyesters. Various products and intermediates were found to have no inhibitory action in the P388 lymphocytic leukemia screen. A rearrangement of the ethylene glycol ketal‐protecting group from the initially protected ketone group to a newly formed aldehyde moiety was observed.