Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives
Samo za registrovane korisnike
2007
Autori
Gasi, Katarina M. PenovBrenesel, Maja Dj. Djurendic
Djurendic, Evgenija A.
Sakac, Marija N.
Canadi, Janos J.
Daljev, Jovana J.
Armbruster, Thomas
Andrić, Silvana A.
Sladić, Dušan
Božić, Tatjana T.
Novaković, Irena T.
Juranić, Zorica D.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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 mu M. (c) 2006 Elsevier Inc. All rights reserved.
Ključne reči:
androst-5-ene derivatives / picolyl and picolinylidene derivatives / aromatase inhibition / antibacterial activity / antitumor activity / X-ray analysisIzvor:
Steroids, 2007, 72, 1, 31-40Izdavač:
- Elsevier Science Inc, New York
Finansiranje / projekti:
- 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
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Gasi, Katarina M. Penov AU - Brenesel, Maja Dj. Djurendic AU - Djurendic, Evgenija A. AU - Sakac, Marija N. AU - Canadi, Janos J. AU - Daljev, Jovana J. AU - Armbruster, Thomas AU - Andrić, Silvana A. AU - Sladić, Dušan AU - Božić, Tatjana T. AU - Novaković, Irena T. AU - Juranić, Zorica D. PY - 2007 UR - https://cherry.chem.bg.ac.rs/handle/123456789/765 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 mu M. (c) 2006 Elsevier Inc. All rights reserved. PB - Elsevier Science Inc, New York 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 = "Gasi, Katarina M. Penov and Brenesel, Maja Dj. Djurendic and Djurendic, Evgenija A. and Sakac, Marija N. and Canadi, Janos J. and Daljev, Jovana J. and Armbruster, Thomas and Andrić, Silvana A. and Sladić, Dušan and Božić, Tatjana T. and Novaković, Irena T. and Juranić, Zorica D.", 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 mu M. (c) 2006 Elsevier Inc. All rights reserved.", publisher = "Elsevier Science Inc, New York", 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" }
Gasi, K. M. P., Brenesel, M. Dj. D., Djurendic, E. A., Sakac, M. N., Canadi, J. J., Daljev, J. J., Armbruster, T., Andrić, S. A., Sladić, D., Božić, T. T., Novaković, I. T.,& Juranić, Z. D.. (2007). Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives. in Steroids Elsevier Science Inc, New York., 72(1), 31-40. https://doi.org/10.1016/j.steroids.2006.10.002
Gasi KMP, Brenesel MDD, Djurendic EA, Sakac MN, Canadi JJ, Daljev JJ, Armbruster T, Andrić SA, Sladić D, Božić TT, Novaković IT, Juranić ZD. 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 .
Gasi, Katarina M. Penov, Brenesel, Maja Dj. Djurendic, Djurendic, Evgenija A., Sakac, Marija N., Canadi, Janos J., Daljev, Jovana J., Armbruster, Thomas, Andrić, Silvana A., Sladić, Dušan, Božić, Tatjana T., Novaković, Irena T., Juranić, Zorica D., "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 . .