Synthesis of dehydroepiandrosterone analogues modified with phosphatidic acid moiety.
Dehydroepiandrosterone (DHEA) and its metabolite 7α-OH DHEA have many diverse physiological, biological and biochemical effects encompassing various cell types, tissues and organs. In in vitro studies, DHEA analogues have myriad biological actions, but in vivo, especially in oral administration, DHEA produces far more limited clinical effects. One of the possible solutions of this problem is conversion of DHEA to active analogues and/or its transformation into prodrug form. In this article, the studies on the conversion of DHEA and 7α-OH DHEA into their phosphatides by the phosphodiester approach are described. In this esterification, N,N-dicyclohexylcarbodiimide (DCC) was the most efficient coupling agent as well as p-toluenesulphonyl chloride (TsCl).
Smuga
Damian A
DA
Department of Chemistry, Wrocław University of Environmental and Life Sciences,Wrocław, Poland.
Smuga
Małgorzata
M
Swizdor
Alina
A
Panek
Anna
A
Wawrzeńczyk
Czesław
C
D000818:Animals; D001711:Biotransformation; D003687:Dehydroepiandrosterone / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000138:chemical synthesis* / Q000378:metabolism; D005670:Fusarium / Q000378:metabolism; D054709:Lecithins / Q000378:metabolism; D010712:Phosphatidic Acids / Q000737:chemistry*; D010739:Phospholipase D / Q000378:metabolism; D011355:Prodrugs / Q000378:metabolism; D013302:Streptomyces / Q000201:enzymology
D054709:Lecithins; D010712:Phosphatidic Acids; D011355:Prodrugs; D003687:Dehydroepiandrosterone; D010739:Phospholipase D