Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds.
A simple approach to aromatization of steroidal quinols and epoxyquinols using a catalytic amount of TMSOTf is reported. Beside acetylation of the angular OH, the acid-catalyzed (TfOH) dienone-phenol rearrangement occurred affording "para" products, or in the case of blocked position 4, the acetoxy group 1,2-migration leads to the formation of "meta" products. Using epoxyquinol derivative as a substrate, the acetoxy group elimination was observed, followed by acid-catalyzed epoxy-ring opening and subsequent double bond migration, giving as a final product Delta(9,11)A-ring aromatized compounds. Synthesis of conduritol-like compounds and structure confirmation by X-ray crystallography of the precursor of steroidal conduritol is also described. In addition, the results of extensive antiproliferative screening against a panel of 60 cancer cell lines are presented.
Milić
Dragana
D
Faculty of Chemistry University of Belgrade, Studentski trg 12-16, POB 158, 11000 Belgrade, Serbia and Montenegro. dmilic@chem.bg.ac.yu
Kop
Tatjana
T
Juranić
Zorica
Z
Gasić
Miroslav J
MJ
Tinant
Bernard
B
Pocsfalvi
Gabriella
G
Solaja
Bogdan A
BA
D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D053138:Cyclohexenes; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006873:Hydroquinones / Q000737:chemistry; D015394:Molecular Structure
D003511:Cyclohexanols; D053138:Cyclohexenes; D006841:Hydrocarbons, Aromatic; D006873:Hydroquinones; C090988:conduritol B