35339-66-3Relevant academic research and scientific papers
Synthesis of oxygenated cholesterols as structural mimics of phorbol ester-type tumor promoters
Endo,Fukasawa,Hashimoto,Shudo
, p. 462 - 469 (1994)
We designed several oxygenated steroids in which functional groups including a hydrophobic group are arranged analogously to those of phorbol ester (12-O-tetradecanoylphorbol-13-acetate, TPA), with the aim of finding compounds with TPA-like activity, but having a different skeleton and a rigid conformation. The designed steroids, 1β,5α-dihydroxy-3β- hydroxymethylcholestan-6-one (4), 3β,5α-dihydroxycholestan-6-one (5), 3β- hydroxymethylcholestan-5α-ol-6-one (6) and 1β,3β,5α-trihydroxycholestan- 6-one (7), were synthesized. A related oxygenated steroid isolated from soft coral, cholestane-1β,3β,5α,6β-tetrol (8), was also synthesized. Among these analogs, compound 7 showed weak TPA-like activities in three biological tests: inhibition of [3H]TPA binding to protein kinase C and to cytosolic- nuclear tumor promoter-binding protein (CN-TPBP), and induction of differentiation of human promyelocytic leukemia cells (HL-60) to monocyte- like cells. On the other hand, compound 5 was found to be a specific ligand for CN-TPBP, but lacked the other TPA-like activities.
Sterols in Marine Invertebrates. 49. Isolation and Structure Elucidation of Eight New Polyhydroxylated Sterols from the Soft Coral Sinularia dissecta
Jagodzinska, Barbara M.,Trimmer, James S.,Fenical, William,Djerassi, Carl
, p. 1435 - 1439 (1985)
A new group of polyhydroxylated sterols - all of them possessing an 11α-hydroxy substituents of potential utility as corticosteroid intermediates - has been isolated from the soft coral Sinularia dissecta.Their general structure was deduced from spectral data (500-MHz and 360-MHz 1H and 13C NMR and MS) and their stereochemistry was determined by correlating the respective spectral data (1H and 13C NMR) with those of synthetic sterols with similar structure and known configuration.
