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.
TY - 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 . .
