Synthesis of S-(28a-homobetulin-28a-yl) thiophosphate, thiophosphonate, and thiophosphinate

0464036 - ÚEB 2017 RIV GB eng J - Journal Article
Sidoryk, K. - Cmoch, P. - Rárová, L. - Oklešťková, Jana - Pakulski, Z. - Strnad, Miroslav
Synthesis of S-(28a-homobetulin-28a-yl) thiophosphate, thiophosphonate, and thiophosphinate.
Phosphorus, Sulfur and Silicon and the Related Elements. Roč. 191, č. 9 (2016), s. 1240-1244. ISSN 1042-6507. E-ISSN 1563-5325
R&D Projects: GA MŠMT(CZ) LO1204; GA ČR GA14-19590S
Institutional support: RVO:61389030
Keywords : terpenoids * homothiophosphabetulin * Homothiobetulin
Subject RIV: EB - Genetics ; Molecular Biology
Impact factor: 0.809, year: 2016

A concise synthesis of thiophosphate, phenylthiophosphonate, and diphenylthiophosphinate esters bearing a 28a-homolupane residue is reported. The new triterpenes were obtained from the readily available 3-O-acetylichopanol by a nucleophilic substitution of the corresponding mesylate with thiocyanate ion followed by a Michaelis-Arbuzov reaction. These results open the way to new lupane-type derivatives having a thiophosphorus moiety at the lupane core as potential anticancer compounds. Additionally, the cytotoxic activities of the new homolupane compounds were evaluated in vitro.
Permanent Link: http://hdl.handle.net/11104/0263101