Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity
Нема приказа
Аутори
Šolaja, Bogdan A.Terzić-Jovanović, Nataša
Pocsfalvi, G
Gerena, L
Tinant, B
Opsenica, Dejan M.
Milhous, WK
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Mixed 1,2,4,5-tetraoxanes possessing simple spirocycloalkane and spirocholic acid-derived substituents were prepared and shown to have significantly higher in vitro antimalarial activity than bis-substituted tetraoxanes. Out of 41 synthesized tetraoxanes, 12 were in vitro more potent against Plasmodium falciparum chloroquine-resistant W2 clone than artemisinin, and the most potent one was 2.4 times as active as arteether. In addition, 9 compounds exhibit higher activity than chloroquine against P. falciparum chloroquine-susceptible D6 clone. Cytotoxicity was assessed for most active compounds against the Vero cell line, showing a cytotoxicity/antimalarial potency ratio of 1/(1400-9500). For the first time, tetraoxanes were screened against Mycobacterium tuberculosis with MICs as low as 4.73 muM against H37Rv strain. Mixed tetraoxanes were synthesized in a simple procedure from cholic acid methyl esters by direct coupling of steroidal gem-dihydroperoxide to simple ketones and further tr...ansformed into corresponding acids and amides.
Извор:
Journal of Medicinal Chemistry, 2002, 45, 16, 3331-3336Издавач:
- Amer Chemical Soc, Washington
DOI: 10.1021/jm020891g
ISSN: 0022-2623
PubMed: 12139444
WoS: 000177142800002
Scopus: 2-s2.0-0036682037
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Šolaja, Bogdan A. AU - Terzić-Jovanović, Nataša AU - Pocsfalvi, G AU - Gerena, L AU - Tinant, B AU - Opsenica, Dejan M. AU - Milhous, WK PY - 2002 UR - https://cherry.chem.bg.ac.rs/handle/123456789/500 AB - Mixed 1,2,4,5-tetraoxanes possessing simple spirocycloalkane and spirocholic acid-derived substituents were prepared and shown to have significantly higher in vitro antimalarial activity than bis-substituted tetraoxanes. Out of 41 synthesized tetraoxanes, 12 were in vitro more potent against Plasmodium falciparum chloroquine-resistant W2 clone than artemisinin, and the most potent one was 2.4 times as active as arteether. In addition, 9 compounds exhibit higher activity than chloroquine against P. falciparum chloroquine-susceptible D6 clone. Cytotoxicity was assessed for most active compounds against the Vero cell line, showing a cytotoxicity/antimalarial potency ratio of 1/(1400-9500). For the first time, tetraoxanes were screened against Mycobacterium tuberculosis with MICs as low as 4.73 muM against H37Rv strain. Mixed tetraoxanes were synthesized in a simple procedure from cholic acid methyl esters by direct coupling of steroidal gem-dihydroperoxide to simple ketones and further transformed into corresponding acids and amides. PB - Amer Chemical Soc, Washington T2 - Journal of Medicinal Chemistry T1 - Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity VL - 45 IS - 16 SP - 3331 EP - 3336 DO - 10.1021/jm020891g ER -
@article{ author = "Šolaja, Bogdan A. and Terzić-Jovanović, Nataša and Pocsfalvi, G and Gerena, L and Tinant, B and Opsenica, Dejan M. and Milhous, WK", year = "2002", abstract = "Mixed 1,2,4,5-tetraoxanes possessing simple spirocycloalkane and spirocholic acid-derived substituents were prepared and shown to have significantly higher in vitro antimalarial activity than bis-substituted tetraoxanes. Out of 41 synthesized tetraoxanes, 12 were in vitro more potent against Plasmodium falciparum chloroquine-resistant W2 clone than artemisinin, and the most potent one was 2.4 times as active as arteether. In addition, 9 compounds exhibit higher activity than chloroquine against P. falciparum chloroquine-susceptible D6 clone. Cytotoxicity was assessed for most active compounds against the Vero cell line, showing a cytotoxicity/antimalarial potency ratio of 1/(1400-9500). For the first time, tetraoxanes were screened against Mycobacterium tuberculosis with MICs as low as 4.73 muM against H37Rv strain. Mixed tetraoxanes were synthesized in a simple procedure from cholic acid methyl esters by direct coupling of steroidal gem-dihydroperoxide to simple ketones and further transformed into corresponding acids and amides.", publisher = "Amer Chemical Soc, Washington", journal = "Journal of Medicinal Chemistry", title = "Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity", volume = "45", number = "16", pages = "3331-3336", doi = "10.1021/jm020891g" }
Šolaja, B. A., Terzić-Jovanović, N., Pocsfalvi, G., Gerena, L., Tinant, B., Opsenica, D. M.,& Milhous, W.. (2002). Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity. in Journal of Medicinal Chemistry Amer Chemical Soc, Washington., 45(16), 3331-3336. https://doi.org/10.1021/jm020891g
Šolaja BA, Terzić-Jovanović N, Pocsfalvi G, Gerena L, Tinant B, Opsenica DM, Milhous W. Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity. in Journal of Medicinal Chemistry. 2002;45(16):3331-3336. doi:10.1021/jm020891g .
Šolaja, Bogdan A., Terzić-Jovanović, Nataša, Pocsfalvi, G, Gerena, L, Tinant, B, Opsenica, Dejan M., Milhous, WK, "Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity" in Journal of Medicinal Chemistry, 45, no. 16 (2002):3331-3336, https://doi.org/10.1021/jm020891g . .