TY  - JOUR
AU  - Opsenica, Dejan
AU  - Pocsfalvi, Gabriella
AU  - Juranić, Zorica
AU  - Tinant, Bernard
AU  - Declercq, J.-P.
AU  - Kyle, D.E.
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan
PY  - 2000
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/21
AB  - Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be ~2 times as active as the trans against Plasmodium falciparum D6 and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PHA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity
VL  - 43
IS  - 17
SP  - 3274
EP  - 3282
DO  - 10.1021/jm000952f
ER  - 

@article{
author = "Opsenica, Dejan and Pocsfalvi, Gabriella and Juranić, Zorica and Tinant, Bernard and Declercq, J.-P. and Kyle, D.E. and Milhous, Wilbur K. and Šolaja, Bogdan",
year = "2000",
abstract = "Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be ~2 times as active as the trans against Plasmodium falciparum D6 and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PHA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity",
volume = "43",
number = "17",
pages = "3274-3282",
doi = "10.1021/jm000952f"
}

Opsenica, D., Pocsfalvi, G., Juranić, Z., Tinant, B., Declercq, J.-P., Kyle, D.E., Milhous, W. K.,& Šolaja, B.. (2000). Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 43(17), 3274-3282.
https://doi.org/10.1021/jm000952f

Opsenica D, Pocsfalvi G, Juranić Z, Tinant B, Declercq J, Kyle D, Milhous WK, Šolaja B. Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity. in Journal of Medicinal Chemistry. 2000;43(17):3274-3282.
doi:10.1021/jm000952f .

Opsenica, Dejan, Pocsfalvi, Gabriella, Juranić, Zorica, Tinant, Bernard, Declercq, J.-P., Kyle, D.E., Milhous, Wilbur K., Šolaja, Bogdan, "Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity" in Journal of Medicinal Chemistry, 43, no. 17 (2000):3274-3282,
https://doi.org/10.1021/jm000952f . .

TY  - JOUR
AU  - Tinant, Bernard
AU  - Declercq, J P
AU  - Dabović, Milan
AU  - Krstić, Natalija
AU  - Lorenc, Ljubinka
AU  - Mihailović, Milhailo Lj.
PY  - 1993
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2704
AB  - The molecular structure of the title compound, which might be a possible intermediate in the synthesis of 5,10:8,9‐diseco‐steroids (=steroklastanes), was determined by X‐ray analysis. Hydrogen bonding between the 5α‐hydroxyl group and the 9‐oxo function attached to the ten‐membered ring, and the presence of two conformational forms of the side‐chain in the solid state structure of 2 are established. Copyright © 1993 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
PB  - Comltb van Beheer van het Bulletin V.Z.W.
T2  - Bulletin des Sociétés Chimiques Belges
T1  - Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate
VL  - 102
IS  - 8
SP  - 539
EP  - 544
DO  - 10.1002/bscb.19931020806
ER  - 

@article{
author = "Tinant, Bernard and Declercq, J P and Dabović, Milan and Krstić, Natalija and Lorenc, Ljubinka and Mihailović, Milhailo Lj.",
year = "1993",
abstract = "The molecular structure of the title compound, which might be a possible intermediate in the synthesis of 5,10:8,9‐diseco‐steroids (=steroklastanes), was determined by X‐ray analysis. Hydrogen bonding between the 5α‐hydroxyl group and the 9‐oxo function attached to the ten‐membered ring, and the presence of two conformational forms of the side‐chain in the solid state structure of 2 are established. Copyright © 1993 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim",
publisher = "Comltb van Beheer van het Bulletin V.Z.W.",
journal = "Bulletin des Sociétés Chimiques Belges",
title = "Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate",
volume = "102",
number = "8",
pages = "539-544",
doi = "10.1002/bscb.19931020806"
}

Tinant, B., Declercq, J. P., Dabović, M., Krstić, N., Lorenc, L.,& Mihailović, M. Lj.. (1993). Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate. in Bulletin des Sociétés Chimiques Belges
Comltb van Beheer van het Bulletin V.Z.W.., 102(8), 539-544.
https://doi.org/10.1002/bscb.19931020806

Tinant B, Declercq JP, Dabović M, Krstić N, Lorenc L, Mihailović ML. Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate. in Bulletin des Sociétés Chimiques Belges. 1993;102(8):539-544.
doi:10.1002/bscb.19931020806 .

Tinant, Bernard, Declercq, J P, Dabović, Milan, Krstić, Natalija, Lorenc, Ljubinka, Mihailović, Milhailo Lj., "Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate" in Bulletin des Sociétés Chimiques Belges, 102, no. 8 (1993):539-544,
https://doi.org/10.1002/bscb.19931020806 . .