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Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity

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Authors
Šolaja, Bogdan A.
Terzić-Jovanović, Nataša
Pocsfalvi, G
Gerena, L
Tinant, B
Opsenica, Dejan M.
Milhous, WK
Article (Published version)
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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 tr...ansformed into corresponding acids and amides.

Source:
Journal of Medicinal Chemistry, 2002, 45, 16, 3331-3336
Publisher:
  • Amer Chemical Soc, Washington

DOI: 10.1021/jm020891g

ISSN: 0022-2623

PubMed: 12139444

WoS: 000177142800002

Scopus: 2-s2.0-0036682037
[ Google Scholar ]
121
107
URI
https://cherry.chem.bg.ac.rs/handle/123456789/500
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - 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
UR  - Kon_1474
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",
url = "Kon_1474"
}
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
Kon_1474
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
Kon_1474 .
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 .,
Kon_1474 .

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