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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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 analysisSource:
Steroids, 2007, 72, 1, 31-40Publisher:
- Elsevier
Funding / 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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IHTMTY - JOUR AU - Gaši, K.M.P. AU - Brenesel, M.Dj.D. AU - Djurendić, E.A. AU - Sakač, Marija AU - Čanadi, J.J. AU - Daljev, J.J. AU - Armbruster, T. AU - Andrić, Silvana AU - Sladić, Dušan AU - Božić, Tatjana T. AU - Novaković, Irena AU - Juranić, Zorica PY - 2007 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/366 AB - 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 IC50 values being in the range of 4-10 μM. PB - Elsevier T2 - Steroids T1 - Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives VL - 72 IS - 1 SP - 31 EP - 40 DO - 10.1016/j.steroids.2006.10.002 ER -
@article{ author = "Gaši, K.M.P. and Brenesel, M.Dj.D. and Djurendić, E.A. and Sakač, Marija and Čanadi, J.J. and Daljev, J.J. and Armbruster, T. and Andrić, Silvana and Sladić, Dušan and Božić, Tatjana T. and Novaković, Irena and Juranić, Zorica", year = "2007", 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 cell lines, the IC50 values being in the range of 4-10 μM.", publisher = "Elsevier", journal = "Steroids", title = "Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives", volume = "72", number = "1", pages = "31-40", doi = "10.1016/j.steroids.2006.10.002" }
Gaši, K.M.P., Brenesel, M.Dj.D., Djurendić, E.A., Sakač, M., Čanadi, J.J., Daljev, J.J., Armbruster, T., Andrić, S., Sladić, D., Božić, T. T., Novaković, I.,& Juranić, Z.. (2007). Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives. in Steroids Elsevier., 72(1), 31-40. https://doi.org/10.1016/j.steroids.2006.10.002
Gaši K, Brenesel M, Djurendić E, Sakač M, Čanadi J, Daljev J, Armbruster T, Andrić S, Sladić D, Božić TT, Novaković I, Juranić Z. Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives. in Steroids. 2007;72(1):31-40. doi:10.1016/j.steroids.2006.10.002 .
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, "Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives" in Steroids, 72, no. 1 (2007):31-40, https://doi.org/10.1016/j.steroids.2006.10.002 . .