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

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2007
Authors
Gaši, K.M.P.
Brenesel, M.Dj.D.
Djurendić, E.A.
Sakač, Marija
Čanadi, J.J.
Daljev, J.J.
Armbruster, T.
Andrić, Silvana
Sladić, Dušan
Božić, Tatjana T.
Novaković, Irena
Juranić, Zorica
Article (Published version)
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Abstract
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 c...ell lines, the IC50 values being in the range of 4-10 μM.

Keywords:
Androst-5-ene derivatives / Antibacterial activity / Antitumor activity / Aromatase inhibition / Picolyl and picolinylidene derivatives / X-ray analysis
Source:
Steroids, 2007, 72, 1, 31-40
Publisher:
  • Elsevier Science Inc, New York
Projects:
  • Sinteza i fizičko-hemijska ispitivanja odabranih organskih jedinjenja od potencijalnog farmakološkog značaja (RS-142052)

DOI: 10.1016/j.steroids.2006.10.002

ISSN: 0039-128X

PubMed: 17118415

WoS: 000243861100004

Scopus: 2-s2.0-33846020540
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/366
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IHTM

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