TY  - JOUR
AU  - Šolaja, Bogdan
AU  - Terzić, Nataša
AU  - Pocsfalvi, Gabriella
AU  - Gerena, L.
AU  - Tinant, Bernard
AU  - Opsenica, Dejan
AU  - Milhous, Wilbur K.
PY  - 2002
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/91
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 μM 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  - American Chemical Society (ACS)
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 and Terzić, Nataša and Pocsfalvi, Gabriella and Gerena, L. and Tinant, Bernard and Opsenica, Dejan and Milhous, Wilbur K.",
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 μM 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 = "American Chemical Society (ACS)",
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., Terzić, N., Pocsfalvi, G., Gerena, L., Tinant, B., Opsenica, D.,& Milhous, W. K.. (2002). Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 45(16), 3331-3336.
https://doi.org/10.1021/jm020891g

Šolaja B, Terzić N, Pocsfalvi G, Gerena L, Tinant B, Opsenica D, Milhous WK. 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, Terzić, Nataša, Pocsfalvi, Gabriella, Gerena, L., Tinant, Bernard, Opsenica, Dejan, Milhous, Wilbur K., "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 . .