Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives

Starting from dehydroepiandrosterone ( 1) 17-picolyl ( 2), 17-picolinylidene ( 7), 17-picolinylidene-16-one ( 10 and 11), and 17-picolyl-16-one ( 15) derivatives of androst-5-ene were synthesized in one, two, four and five steps respectively. By the Oppenauer oxidation or dehydration of 2, 7, 10, an...

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Bibliographic Details
Published in:	Steroids Vol. 72; no. 1; pp. 31 - 40
Main Authors:	Gaši, Katarina M. Penov, Brenesel, Maja Dj. Djurendić, Djurendić, Evgenija A., Sakač, Marija N., Čanadi, Janoš J., Daljev, Jovana J., Armbruster, Thomas, Andrić, Silvana, Sladić, Dušan M., Božić, Tatjana T., Novaković, Irena T., Juranić, Zorica D.
Format:	Journal Article
Language:	English
Published:	New York, NY Elsevier Inc 2007 Elsevier Science
Subjects:	Androst-5-ene derivatives Androstenes - chemical synthesis Androstenes - chemistry Androstenes - pharmacology Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial activity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antitumor activity Aromatase - metabolism Aromatase inhibition Aromatase Inhibitors - chemical synthesis Aromatase Inhibitors - chemistry Aromatase Inhibitors - pharmacology Biological and medical sciences Cell Line, Tumor Female Fundamental and applied biological sciences. Psychology Humans Inhibitory Concentration 50 Melanoma - drug therapy Molecular Structure Picolyl and picolinylidene derivatives Structure-Activity Relationship Vertebrates: endocrinology X-ray analysis Antibacterial activity Antitumor activity X-ray analysis Androst-5-ene derivatives Picolyl and picolinylidene derivatives Aromatase inhibition Antineoplastic agent Enzyme Biosynthesis X ray Estrogen synthase derivatives Inhibition Antibacterial agent Picolyl and picolinylidene
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Summary:	Starting from dehydroepiandrosterone ( 1) 17-picolyl ( 2), 17-picolinylidene ( 7), 17-picolinylidene-16-one ( 10 and 11), and 17-picolyl-16-one ( 15) derivatives of androst-5-ene were synthesized in one, two, four and five steps respectively. By the Oppenauer oxidation or dehydration of 2, 7, 10, and 11 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), the corresponding A and B ring modified derivatives 3, 5, 6, 8, 9, and 12– 14 were obtained. The structure of 2 was unambiguously proved by the appropriate X-ray structural analysis. Compounds 3, 5, 9, 12– 14 showed inhibitory activity against the enzyme aromatase. Antibacterial activity, toxicity to brine shrimp Artemia salina, antitumor activity against three tumor cell lines (human cervix carcinoma HeLa cells, human melanoma FemX cells, and human myelogenous leukemia K562 cells) and toxicity against peripheral blood mononuclear cells were evaluated. Three tested compounds, namely 11, 13, and 15, showed strong activity against all three cell lines, the IC 50 values being in the range of 4–10 μM.
ISSN:	0039-128X 1878-5867
DOI:	10.1016/j.steroids.2006.10.002