Oxazoline derivatives of [17(20)<Emphasis Type="Italic">E</Emphasis>]-21-norpregnene – inhibitors of CYP17A1 activity and proliferation of prostate carcinoma cells

Nine new oxazolinyl derivatives of [17(20)E]-21-norpregnene, differing in the structure of steroid moiety, were investigated for their potency to inhibit the CYP17A1 catalytic activity, as well as growth and proliferation of LNCaP and PC-3 prostate carcinoma cell lines. The activity of one of the investigated compounds, 2´-{[(E)3β-hydroxyandrost-5-en-17-ylidene]methyl}-4´,5´-dihydro-1´,3´-oxazole (1), was found to be comparable with that of Abiraterone, a known inhibitor of CYP17A1 used for treatment of prostate cancer. A model of the interaction of oxazoline 1 with the active site of CYP17A1 was constructed by the molecular dynamics method. A correlation was found between the structure and the biological activity in the series of [17(20)E]-21-norpregnene oxazolinyl derivatives.     

Synthesis of nitrogen-containing derivatives of 17(20)-pregnenoic, 17β-hydroxypregnanoic,and 17α-hydroxypregnanoic acids as new potential antiandrogens

A general scheme for the synthesis of oxazoline and benzoxazole derivatives of [17(20)E]-21-norpregnene differing in the structure of the steroid moiety as well as amides of 17β-hydroxy-3-oxopregn-4-en-21-oic and 17α-hydroxy-3-oxopregn-4-en-21-oic acids was developed. The scheme involved synthesis of the steroid building blocks (appropriately protected derivatives of pregn-17(20)-en-21-oic, 17β-hydroxypregnan-21-oic, and 17α-hydroxypregnan-21-oic acids) and subsequent transformation of these building blocks into the target compounds. Following the developed scheme, synthesis of new nitrogen-containing steroid derivatives exhibiting antiandrogenic activity was enabled.     

Photosensitizing Activity of Steroid Derivatives of Pyropheophorbide in the Oxidation of Tryptophan in the Aqueous Phase

Russian Journal of Physical Chemistry A - Solubilization with pluronic F-127 gave water-soluble forms of hydrophobic photosensitizers—steroid derivatives of pyropheophorbide a. Solubilization...     

Synthesis of E- and Z-isomeric progesterone 3-O-methyloximes

Isomeric E- and Z-3-methoxyiminopregn-4-en-20-ones were obtained from progesterone by selective ketalization of 20-oxo group, subsequent oximation of the remaining 3-keto group, removal of the protecting group, and chromatographic separation of isomers.