Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity
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Todorović, Nevena M.Stefanović, Milutin
Tinant, B
Declercq, JP
Makler, MT
Šolaja, Bogdan A.
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Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5 alpha- and 5 beta-cholestan-3-ones by acid-catalyzed addition of hydrogen peroxide to the ketone. They were characterized by IR, NMR, and mass spectroscopy analysis aided by molecular mechanics calculations, and, in the instance of 5 beta-cholestane-3 alpha,3 beta-dihydroperoxide (6), by x-ray analysis. The synthesized compounds were tested in vitro against Plasmodium falciparum Sierra Leone (D6) and Indochina (W2) malaria clones. All compounds were inactive to both clones, with the exception of tetraoxane 7a, which exhibited modest activity toward D6 clone with IC50 = 155 nM. (C) 1996 by Elsevier Science Inc.
Keywords:
gem-dihydroperoxide / peroxide / tetraoxane / molecular mechanics / antimalarial activitySource:
Steroids, 1996, 61, 12, 688-696Publisher:
- Elsevier Science Inc, New York
DOI: 10.1016/S0039-128X(96)00203-6
ISSN: 0039-128X
PubMed: 8987137
WoS: A1996VY35500003
Scopus: 2-s2.0-0030477376
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Todorović, Nevena M. AU - Stefanović, Milutin AU - Tinant, B AU - Declercq, JP AU - Makler, MT AU - Šolaja, Bogdan A. PY - 1996 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2582 AB - Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5 alpha- and 5 beta-cholestan-3-ones by acid-catalyzed addition of hydrogen peroxide to the ketone. They were characterized by IR, NMR, and mass spectroscopy analysis aided by molecular mechanics calculations, and, in the instance of 5 beta-cholestane-3 alpha,3 beta-dihydroperoxide (6), by x-ray analysis. The synthesized compounds were tested in vitro against Plasmodium falciparum Sierra Leone (D6) and Indochina (W2) malaria clones. All compounds were inactive to both clones, with the exception of tetraoxane 7a, which exhibited modest activity toward D6 clone with IC50 = 155 nM. (C) 1996 by Elsevier Science Inc. PB - Elsevier Science Inc, New York T2 - Steroids T1 - Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity VL - 61 IS - 12 SP - 688 EP - 696 DO - 10.1016/S0039-128X(96)00203-6 ER -
@article{ author = "Todorović, Nevena M. and Stefanović, Milutin and Tinant, B and Declercq, JP and Makler, MT and Šolaja, Bogdan A.", year = "1996", abstract = "Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5 alpha- and 5 beta-cholestan-3-ones by acid-catalyzed addition of hydrogen peroxide to the ketone. They were characterized by IR, NMR, and mass spectroscopy analysis aided by molecular mechanics calculations, and, in the instance of 5 beta-cholestane-3 alpha,3 beta-dihydroperoxide (6), by x-ray analysis. The synthesized compounds were tested in vitro against Plasmodium falciparum Sierra Leone (D6) and Indochina (W2) malaria clones. All compounds were inactive to both clones, with the exception of tetraoxane 7a, which exhibited modest activity toward D6 clone with IC50 = 155 nM. (C) 1996 by Elsevier Science Inc.", publisher = "Elsevier Science Inc, New York", journal = "Steroids", title = "Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity", volume = "61", number = "12", pages = "688-696", doi = "10.1016/S0039-128X(96)00203-6" }
Todorović, N. M., Stefanović, M., Tinant, B., Declercq, J., Makler, M.,& Šolaja, B. A.. (1996). Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity. in Steroids Elsevier Science Inc, New York., 61(12), 688-696. https://doi.org/10.1016/S0039-128X(96)00203-6
Todorović NM, Stefanović M, Tinant B, Declercq J, Makler M, Šolaja BA. Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity. in Steroids. 1996;61(12):688-696. doi:10.1016/S0039-128X(96)00203-6 .
Todorović, Nevena M., Stefanović, Milutin, Tinant, B, Declercq, JP, Makler, MT, Šolaja, Bogdan A., "Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity" in Steroids, 61, no. 12 (1996):688-696, https://doi.org/10.1016/S0039-128X(96)00203-6 . .