Several dicyclohexylidene tetraoxanes were prepared in order to gain a further insight into structure-activity relationship of this kind of antimalarials. The tetraoxanes 2-5, obtained as a cis/trans mixture, showed pronounced antimalarial activity against Plasmodium falciparum chloroquine susceptible D6, chloroquine resistant W2 and multidrug-resistant TM91C235 (Thailand) strains. They have better than or similar activity to the corresponding desmethyl dicyclohexylidene derivatives. Two chimeric endoperoxides with superior antimalarial activity to the natural product ascaridole were also synthesized.
U ovom radu prikazana je sinteza nekoliko dicikiloheksilidenskih tetraoksana u cilju sagledavanja odnosa struktura-aktivnost ove vrste antimalarika. Jedinjenja 2-5 dobijena kao (cis,trans)-smese pokazala su izraženu antimalarijsku aktivnost prema D6, W2 i TM91C235 (Thailand) sojevima P. falciparum. Ona imaju bolju ili sličnu aktivnost od odgovarajućih desmetil cikloheksilidenskih derivata. Sintetisana su i dva endoperoksida himerne strukture znatno izraženije aktivnosti od prirodnog proizvoda askaridola. .
Keywords:
mixed tetraoxanes / endoperoxides / malaria / P. falciparum
Source:
Journal of the Serbian Chemical Society, 2007, 72, 12, 1181-1190
TY - JOUR
AU - Opsenica, Igor
AU - Opsenica, Dejan
AU - Jadranin, Milka
AU - Smith, Kirsten
AU - Milhous, Wilbur K.
AU - Stratakis, Manolis
AU - Šolaja, Bogdan
PY - 2007
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/303
AB - Several dicyclohexylidene tetraoxanes were prepared in order to gain a further insight into structure-activity relationship of this kind of antimalarials. The tetraoxanes 2-5, obtained as a cis/trans mixture, showed pronounced antimalarial activity against Plasmodium falciparum chloroquine susceptible D6, chloroquine resistant W2 and multidrug-resistant TM91C235 (Thailand) strains. They have better than or similar activity to the corresponding desmethyl dicyclohexylidene derivatives. Two chimeric endoperoxides with superior antimalarial activity to the natural product ascaridole were also synthesized.
AB - U ovom radu prikazana je sinteza nekoliko dicikiloheksilidenskih tetraoksana u cilju sagledavanja odnosa struktura-aktivnost ove vrste antimalarika. Jedinjenja 2-5 dobijena kao (cis,trans)-smese pokazala su izraženu antimalarijsku aktivnost prema D6, W2 i TM91C235 (Thailand) sojevima P. falciparum. Ona imaju bolju ili sličnu aktivnost od odgovarajućih desmetil cikloheksilidenskih derivata. Sintetisana su i dva endoperoksida himerne strukture znatno izraženije aktivnosti od prirodnog proizvoda askaridola. .
PB - Serbian Chemical Society
T2 - Journal of the Serbian Chemical Society
T1 - On peroxide antimalarials
T1 - O peroksidnim antimalaricima
VL - 72
IS - 12
SP - 1181
EP - 1190
DO - 10.2298/JSC0712181O
ER -
@article{
author = "Opsenica, Igor and Opsenica, Dejan and Jadranin, Milka and Smith, Kirsten and Milhous, Wilbur K. and Stratakis, Manolis and Šolaja, Bogdan",
year = "2007",
abstract = "Several dicyclohexylidene tetraoxanes were prepared in order to gain a further insight into structure-activity relationship of this kind of antimalarials. The tetraoxanes 2-5, obtained as a cis/trans mixture, showed pronounced antimalarial activity against Plasmodium falciparum chloroquine susceptible D6, chloroquine resistant W2 and multidrug-resistant TM91C235 (Thailand) strains. They have better than or similar activity to the corresponding desmethyl dicyclohexylidene derivatives. Two chimeric endoperoxides with superior antimalarial activity to the natural product ascaridole were also synthesized., U ovom radu prikazana je sinteza nekoliko dicikiloheksilidenskih tetraoksana u cilju sagledavanja odnosa struktura-aktivnost ove vrste antimalarika. Jedinjenja 2-5 dobijena kao (cis,trans)-smese pokazala su izraženu antimalarijsku aktivnost prema D6, W2 i TM91C235 (Thailand) sojevima P. falciparum. Ona imaju bolju ili sličnu aktivnost od odgovarajućih desmetil cikloheksilidenskih derivata. Sintetisana su i dva endoperoksida himerne strukture znatno izraženije aktivnosti od prirodnog proizvoda askaridola. .",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "On peroxide antimalarials, O peroksidnim antimalaricima",
volume = "72",
number = "12",
pages = "1181-1190",
doi = "10.2298/JSC0712181O"
}
Opsenica, I., Opsenica, D., Jadranin, M., Smith, K., Milhous, W. K., Stratakis, M.,& Šolaja, B.. (2007). On peroxide antimalarials. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 72(12), 1181-1190.
https://doi.org/10.2298/JSC0712181O
Opsenica I, Opsenica D, Jadranin M, Smith K, Milhous WK, Stratakis M, Šolaja B. On peroxide antimalarials. in Journal of the Serbian Chemical Society. 2007;72(12):1181-1190.
doi:10.2298/JSC0712181O .
Opsenica, Igor, Opsenica, Dejan, Jadranin, Milka, Smith, Kirsten, Milhous, Wilbur K., Stratakis, Manolis, Šolaja, Bogdan, "On peroxide antimalarials" in Journal of the Serbian Chemical Society, 72, no. 12 (2007):1181-1190,
https://doi.org/10.2298/JSC0712181O . .
