TY  - JOUR
AU  - Milić, Dragana
AU  - Kop, Tatjana
AU  - Juranić, Z.
AU  - Gasic, MJ
AU  - Tinant, B
AU  - Pocsfalvi, G
AU  - Šolaja, Bogdan A.
PY  - 2005
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/748
AB  - A simple approach to aromatization of steroidal quinols and epoxyquinols using a catalytic amount of TMSOTf is reported. Beside acetylation of the angular OH, the acid-catalyzed (TfOH) dienone-phenol rearrangement occurred affording "para" products, or in the case of blocked position 4, the acetoxy group 1,2-migration leads to the formation of "meta" products. Using epoxyquinol derivative as a substrate, the acetoxy group elimination was observed, followed by acid-catalyzed epoxy-ring opening and subsequent double bond migration, giving as a final product Delta(9,11) A-ring aromatized compounds. Synthesis of conduritol-like compounds and structure confirmation by X-ray crystallography of the precursor of steroidal conduritol is also described. In addition, the results of extensive antiproliferative screening against a panel of 60 cancer cell lines are presented. (c) 2005 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Steroids
T1  - Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds
VL  - 70
IS  - 14
SP  - 922
EP  - 932
DO  - 10.1016/j.steroids.2005.07.001
ER  - 

@article{
author = "Milić, Dragana and Kop, Tatjana and Juranić, Z. and Gasic, MJ and Tinant, B and Pocsfalvi, G and Šolaja, Bogdan A.",
year = "2005",
abstract = "A simple approach to aromatization of steroidal quinols and epoxyquinols using a catalytic amount of TMSOTf is reported. Beside acetylation of the angular OH, the acid-catalyzed (TfOH) dienone-phenol rearrangement occurred affording "para" products, or in the case of blocked position 4, the acetoxy group 1,2-migration leads to the formation of "meta" products. Using epoxyquinol derivative as a substrate, the acetoxy group elimination was observed, followed by acid-catalyzed epoxy-ring opening and subsequent double bond migration, giving as a final product Delta(9,11) A-ring aromatized compounds. Synthesis of conduritol-like compounds and structure confirmation by X-ray crystallography of the precursor of steroidal conduritol is also described. In addition, the results of extensive antiproliferative screening against a panel of 60 cancer cell lines are presented. (c) 2005 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Steroids",
title = "Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds",
volume = "70",
number = "14",
pages = "922-932",
doi = "10.1016/j.steroids.2005.07.001"
}

Milić, D., Kop, T., Juranić, Z., Gasic, M., Tinant, B., Pocsfalvi, G.,& Šolaja, B. A.. (2005). Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds. in Steroids
Elsevier Science Inc, New York., 70(14), 922-932.
https://doi.org/10.1016/j.steroids.2005.07.001

Milić D, Kop T, Juranić Z, Gasic M, Tinant B, Pocsfalvi G, Šolaja BA. Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds. in Steroids. 2005;70(14):922-932.
doi:10.1016/j.steroids.2005.07.001 .

Milić, Dragana, Kop, Tatjana, Juranić, Z., Gasic, MJ, Tinant, B, Pocsfalvi, G, Šolaja, Bogdan A., "Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds" in Steroids, 70, no. 14 (2005):922-932,
https://doi.org/10.1016/j.steroids.2005.07.001 . .

TY  - JOUR
AU  - Kop, Tatjana
AU  - Pocsfalvi, G
AU  - Šolaja, Bogdan A.
PY  - 2004
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/669
AB  - Synthesis of a steroidal dendrimercore possessing various functional termini, such as ester, carboxy and hydroxy, is presented. The approach described enables further simple manipulations for the introduction of more complex functionalities.
AB  - U ovom radu prikazana je sinteza dendrimerskog steroidnog jezgra sa estarskim karboksilnim i hidroksilnim završecima. Opisani pristup sintezi omogućava dalju, kompleksniju funkcionalizaciju jednostavnim manipulacijama.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis of a steroidal dendrimer core
T1  - Sinteza dendrimerskog steroidnog jezgra
VL  - 69
IS  - 10
SP  - 769
EP  - 775
DO  - 10.2298/JSC0410769K
ER  - 

@article{
author = "Kop, Tatjana and Pocsfalvi, G and Šolaja, Bogdan A.",
year = "2004",
abstract = "Synthesis of a steroidal dendrimercore possessing various functional termini, such as ester, carboxy and hydroxy, is presented. The approach described enables further simple manipulations for the introduction of more complex functionalities., U ovom radu prikazana je sinteza dendrimerskog steroidnog jezgra sa estarskim karboksilnim i hidroksilnim završecima. Opisani pristup sintezi omogućava dalju, kompleksniju funkcionalizaciju jednostavnim manipulacijama.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis of a steroidal dendrimer core, Sinteza dendrimerskog steroidnog jezgra",
volume = "69",
number = "10",
pages = "769-775",
doi = "10.2298/JSC0410769K"
}

Kop, T., Pocsfalvi, G.,& Šolaja, B. A.. (2004). Synthesis of a steroidal dendrimer core. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 69(10), 769-775.
https://doi.org/10.2298/JSC0410769K

Kop T, Pocsfalvi G, Šolaja BA. Synthesis of a steroidal dendrimer core. in Journal of the Serbian Chemical Society. 2004;69(10):769-775.
doi:10.2298/JSC0410769K .

Kop, Tatjana, Pocsfalvi, G, Šolaja, Bogdan A., "Synthesis of a steroidal dendrimer core" in Journal of the Serbian Chemical Society, 69, no. 10 (2004):769-775,
https://doi.org/10.2298/JSC0410769K . .

TY  - JOUR
AU  - Opsenica, Dejan M.
AU  - Angelovski, G
AU  - Pocsfalvi, G
AU  - Juranić, Z.
AU  - Žižak, Željko S.
AU  - Kyle, D
AU  - Milhous, WK
AU  - Šolaja, Bogdan A.
PY  - 2003
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/559
AB  - Several cis and trans bis-steroidal 1,2,4,5-tetraoxanes possessing amide terminus were synthesised and evaluated as antimalarials and antiproliferatives. The compounds exhibited submicromolar antimalarial activity against Plasmodium falciparum D6 and W2 strains. The existence of HN-C(O) moiety was found necessary for pronounced antimalarial and antiproliferative activity. In antiproliferative screen, the trans tetraoxane 6 was found to exhibit a pronounced cytotoxicity on 14 cancer cell lines. In addition, tetraoxanes 11 and 12 exhibited significant cytotoxic activity too; microscopic examination of treated HeLa cells showed morphological appearance reminiscent for apoptosis (condensed and/or fragmented nuclei). (C) 2003 Elsevier Science Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic and Medicinal Chemistry
T1  - Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes
VL  - 11
IS  - 13
SP  - 2761
EP  - 2768
DO  - 10.1016/S0968-0896(03)00224-4
ER  - 

@article{
author = "Opsenica, Dejan M. and Angelovski, G and Pocsfalvi, G and Juranić, Z. and Žižak, Željko S. and Kyle, D and Milhous, WK and Šolaja, Bogdan A.",
year = "2003",
abstract = "Several cis and trans bis-steroidal 1,2,4,5-tetraoxanes possessing amide terminus were synthesised and evaluated as antimalarials and antiproliferatives. The compounds exhibited submicromolar antimalarial activity against Plasmodium falciparum D6 and W2 strains. The existence of HN-C(O) moiety was found necessary for pronounced antimalarial and antiproliferative activity. In antiproliferative screen, the trans tetraoxane 6 was found to exhibit a pronounced cytotoxicity on 14 cancer cell lines. In addition, tetraoxanes 11 and 12 exhibited significant cytotoxic activity too; microscopic examination of treated HeLa cells showed morphological appearance reminiscent for apoptosis (condensed and/or fragmented nuclei). (C) 2003 Elsevier Science Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry",
title = "Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes",
volume = "11",
number = "13",
pages = "2761-2768",
doi = "10.1016/S0968-0896(03)00224-4"
}

Opsenica, D. M., Angelovski, G., Pocsfalvi, G., Juranić, Z., Žižak, Ž. S., Kyle, D., Milhous, W.,& Šolaja, B. A.. (2003). Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes. in Bioorganic and Medicinal Chemistry
Pergamon-Elsevier Science Ltd, Oxford., 11(13), 2761-2768.
https://doi.org/10.1016/S0968-0896(03)00224-4

Opsenica DM, Angelovski G, Pocsfalvi G, Juranić Z, Žižak ŽS, Kyle D, Milhous W, Šolaja BA. Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes. in Bioorganic and Medicinal Chemistry. 2003;11(13):2761-2768.
doi:10.1016/S0968-0896(03)00224-4 .

Opsenica, Dejan M., Angelovski, G, Pocsfalvi, G, Juranić, Z., Žižak, Željko S., Kyle, D, Milhous, WK, Šolaja, Bogdan A., "Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes" in Bioorganic and Medicinal Chemistry, 11, no. 13 (2003):2761-2768,
https://doi.org/10.1016/S0968-0896(03)00224-4 . .

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
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 . .

TY  - JOUR
AU  - Opsenica, Dejan M.
AU  - Pocsfalvi, G
AU  - Milhous, WK
AU  - Šolaja, Bogdan A.
PY  - 2002
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/502
AB  - An intramolecular steroidal 1,2,4,5-tetraoxane has been synthesised in six steps starting from methyl 3-oxo-7alpha,12alpha-diacetoxy-5beta-cholan-24-pate. The synthesised 1,2,4,5-tetra-aoxane has moderate in vitro antimalarial activity against P. falciparum Strains (IC50) (D-6) = 0.35 mug/mL: (IC50 (W2) = 0.29 mug/ML).
AB  - Polazeći od methyl 3-oxo-7α,12α-diacetoxy-5β-cholan-24-oate sintetisan je u šest faza intramolekulski steroidni 1,2,4,5-tetraoksan. Proizvod ima umerenu in vitro antimalarijsku aktivnost prema P. falciparum sojevima (IC50 (D6) = 0.35 µg/mL; IC50 (W2) = 0.29 µg/mL).
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Antimalarial peroxides: the first intramolecular 1,2,4,5-tetraoxane
T1  - Antimalarijski peroksidi - prvi intramolekulski 1,2,4,5-tetraoksan
VL  - 67
IS  - 7
SP  - 465
EP  - 471
DO  - 10.2298/JSC0207465O
ER  - 

@article{
author = "Opsenica, Dejan M. and Pocsfalvi, G and Milhous, WK and Šolaja, Bogdan A.",
year = "2002",
abstract = "An intramolecular steroidal 1,2,4,5-tetraoxane has been synthesised in six steps starting from methyl 3-oxo-7alpha,12alpha-diacetoxy-5beta-cholan-24-pate. The synthesised 1,2,4,5-tetra-aoxane has moderate in vitro antimalarial activity against P. falciparum Strains (IC50) (D-6) = 0.35 mug/mL: (IC50 (W2) = 0.29 mug/ML)., Polazeći od methyl 3-oxo-7α,12α-diacetoxy-5β-cholan-24-oate sintetisan je u šest faza intramolekulski steroidni 1,2,4,5-tetraoksan. Proizvod ima umerenu in vitro antimalarijsku aktivnost prema P. falciparum sojevima (IC50 (D6) = 0.35 µg/mL; IC50 (W2) = 0.29 µg/mL).",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Antimalarial peroxides: the first intramolecular 1,2,4,5-tetraoxane, Antimalarijski peroksidi - prvi intramolekulski 1,2,4,5-tetraoksan",
volume = "67",
number = "7",
pages = "465-471",
doi = "10.2298/JSC0207465O"
}

Opsenica, D. M., Pocsfalvi, G., Milhous, W.,& Šolaja, B. A.. (2002). Antimalarial peroxides: the first intramolecular 1,2,4,5-tetraoxane. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 67(7), 465-471.
https://doi.org/10.2298/JSC0207465O

Opsenica DM, Pocsfalvi G, Milhous W, Šolaja BA. Antimalarial peroxides: the first intramolecular 1,2,4,5-tetraoxane. in Journal of the Serbian Chemical Society. 2002;67(7):465-471.
doi:10.2298/JSC0207465O .

Opsenica, Dejan M., Pocsfalvi, G, Milhous, WK, Šolaja, Bogdan A., "Antimalarial peroxides: the first intramolecular 1,2,4,5-tetraoxane" in Journal of the Serbian Chemical Society, 67, no. 7 (2002):465-471,
https://doi.org/10.2298/JSC0207465O . .

TY  - JOUR
AU  - Opsenica, Dejan M.
AU  - Pocsfalvi, G
AU  - Juranić, Z.
AU  - Tinant, B
AU  - Declercq, JP
AU  - Kyle, DE
AU  - Milhous, WK
AU  - Šolaja, Bogdan A.
PY  - 2000
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/441
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 similar to 2 times as active as the trans against Plasmodium falciparum DG 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 PRA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.
PB  - Amer Chemical Soc, Washington
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 M. and Pocsfalvi, G and Juranić, Z. and Tinant, B and Declercq, JP and Kyle, DE and Milhous, WK and Šolaja, Bogdan A.",
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 similar to 2 times as active as the trans against Plasmodium falciparum DG 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 PRA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.",
publisher = "Amer Chemical Soc, Washington",
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. M., Pocsfalvi, G., Juranić, Z., Tinant, B., Declercq, J., Kyle, D., Milhous, W.,& Šolaja, B. A.. (2000). Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity. in Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 43(17), 3274-3282.
https://doi.org/10.1021/jm000952f

Opsenica DM, Pocsfalvi G, Juranić Z, Tinant B, Declercq J, Kyle D, Milhous W, Šolaja BA. 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 M., Pocsfalvi, G, Juranić, Z., Tinant, B, Declercq, JP, Kyle, DE, Milhous, WK, Šolaja, Bogdan A., "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 . .