Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity
Authorized Users Only
1996
Authors
Todorović, Nina
Stefanović, Milutin
Tinant, Bernard
Declercq, Jean-Paul
Makler, Michael T
Šolaja, Bogdan

Article (Published version)

Elsevier Science Inc.
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Show full item recordAbstract
Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5e~- and 5~3-cholestan3-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 5~3-cholestane3et,3~5-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 IC5o =
155 nM
Keywords:
gem-dihydroperoxide / peroxide / tetraoxane / molecular mechanics / antimalarial activitySource:
Steroids, 1996, 61, 12, 688-696Publisher:
- Elsevier
Funding / projects:
- Serbian Academy of Sciences and Arts, Research Fund of Serbia for financial support (grant 02E4)
DOI: 10.1016/S0039-128X(96)00203-6
ISSN: 0039-128X
PubMed: 8987137
WoS: A1996VY35500003
Scopus: 2-s2.0-0030477376
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IHTMTY - JOUR AU - Todorović, Nina AU - Stefanović, Milutin AU - Tinant, Bernard AU - Declercq, Jean-Paul AU - Makler, Michael T AU - Šolaja, Bogdan PY - 1996 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3995 AB - Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5e~- and 5~3-cholestan3-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 5~3-cholestane3et,3~5-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 IC5o = 155 nM PB - Elsevier 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, Nina and Stefanović, Milutin and Tinant, Bernard and Declercq, Jean-Paul and Makler, Michael T and Šolaja, Bogdan", year = "1996", abstract = "Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5e~- and 5~3-cholestan3-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 5~3-cholestane3et,3~5-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 IC5o = 155 nM", publisher = "Elsevier", 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., Stefanović, M., Tinant, B., Declercq, J., Makler, M. T.,& Šolaja, B.. (1996). Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity. in Steroids Elsevier., 61(12), 688-696. https://doi.org/10.1016/S0039-128X(96)00203-6
Todorović N, Stefanović M, Tinant B, Declercq J, Makler MT, Šolaja B. 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, Nina, Stefanović, Milutin, Tinant, Bernard, Declercq, Jean-Paul, Makler, Michael T, Šolaja, Bogdan, "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 . .