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 . .

TY  - JOUR
AU  - Jovanović, Bratislav Ž.
AU  - Mišić-Vuković, Milica M.
AU  - Vajs, Vlatka
AU  - Čanadi, J. J.
PY  - 1992
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2789
AB  - The 13C N.M.R. spectra of some substituted α-phenylpyridylacrylic acids, α-phenyl, α-(3-pyrydyl) and α-(3-pyrydyl-N-oxide) cinnamic acids were determined in deuterated dimethyl sulfoxide (d6-DMSO). It has been shown that the subsitutent chemical shifts (SCS) for Cβatom ethylenic bond of the examined compounds correlated linearely with the summ of the corresponding substituent constants in the both rings (σx + σY). This correlation was interpreted as evidence that the electronic effects of both substituents are involved in conjugated aromatic system. © 1992.
PB  - Elsevier Science Publishers B.V.
T2  - Journal of Molecular Structure
T1  - Substituent efects on the carbon-13 chemical shifts in α-phenylpyridylacrylic acids
VL  - 267
IS  - C
SP  - 411
EP  - 414
DO  - 10.1016/0022-2860(92)87065-4
ER  - 

@article{
author = "Jovanović, Bratislav Ž. and Mišić-Vuković, Milica M. and Vajs, Vlatka and Čanadi, J. J.",
year = "1992",
abstract = "The 13C N.M.R. spectra of some substituted α-phenylpyridylacrylic acids, α-phenyl, α-(3-pyrydyl) and α-(3-pyrydyl-N-oxide) cinnamic acids were determined in deuterated dimethyl sulfoxide (d6-DMSO). It has been shown that the subsitutent chemical shifts (SCS) for Cβatom ethylenic bond of the examined compounds correlated linearely with the summ of the corresponding substituent constants in the both rings (σx + σY). This correlation was interpreted as evidence that the electronic effects of both substituents are involved in conjugated aromatic system. © 1992.",
publisher = "Elsevier Science Publishers B.V.",
journal = "Journal of Molecular Structure",
title = "Substituent efects on the carbon-13 chemical shifts in α-phenylpyridylacrylic acids",
volume = "267",
number = "C",
pages = "411-414",
doi = "10.1016/0022-2860(92)87065-4"
}

Jovanović, B. Ž., Mišić-Vuković, M. M., Vajs, V.,& Čanadi, J. J.. (1992). Substituent efects on the carbon-13 chemical shifts in α-phenylpyridylacrylic acids. in Journal of Molecular Structure
Elsevier Science Publishers B.V.., 267(C), 411-414.
https://doi.org/10.1016/0022-2860(92)87065-4

Jovanović BŽ, Mišić-Vuković MM, Vajs V, Čanadi JJ. Substituent efects on the carbon-13 chemical shifts in α-phenylpyridylacrylic acids. in Journal of Molecular Structure. 1992;267(C):411-414.
doi:10.1016/0022-2860(92)87065-4 .

Jovanović, Bratislav Ž., Mišić-Vuković, Milica M., Vajs, Vlatka, Čanadi, J. J., "Substituent efects on the carbon-13 chemical shifts in α-phenylpyridylacrylic acids" in Journal of Molecular Structure, 267, no. C (1992):411-414,
https://doi.org/10.1016/0022-2860(92)87065-4 . .