TY  - JOUR
AU  - Bondžić, Bojan
AU  - Eilbracht, Peter
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6806
AB  - A novel one-pot synthesis of tetrahydro-β-carboline systems via tandem hydroformylation–Pictet–Spengler reaction starting from olefins and aryl ethylamines is described. This tandem procedure allows fast and convenient synthesis of various substituted tetrahydro-β-carbolines.
PB  - Royal Society of Chemistry
T2  - Organic and Biomolecular Chemistry
T1  - Syntheses of Tetrahydro-β-Carbolines via Tandem Hydformylation / Pictet-Spengler Reaction, Scope and limitations
VL  - 6
SP  - 4059
EP  - 4063
DO  - 10.1039/B809157A
ER  - 

@article{
author = "Bondžić, Bojan and Eilbracht, Peter",
year = "2008",
abstract = "A novel one-pot synthesis of tetrahydro-β-carboline systems via tandem hydroformylation–Pictet–Spengler reaction starting from olefins and aryl ethylamines is described. This tandem procedure allows fast and convenient synthesis of various substituted tetrahydro-β-carbolines.",
publisher = "Royal Society of Chemistry",
journal = "Organic and Biomolecular Chemistry",
title = "Syntheses of Tetrahydro-β-Carbolines via Tandem Hydformylation / Pictet-Spengler Reaction, Scope and limitations",
volume = "6",
pages = "4059-4063",
doi = "10.1039/B809157A"
}

Bondžić, B.,& Eilbracht, P.. (2008). Syntheses of Tetrahydro-β-Carbolines via Tandem Hydformylation / Pictet-Spengler Reaction, Scope and limitations. in Organic and Biomolecular Chemistry
Royal Society of Chemistry., 6, 4059-4063.
https://doi.org/10.1039/B809157A

Bondžić B, Eilbracht P. Syntheses of Tetrahydro-β-Carbolines via Tandem Hydformylation / Pictet-Spengler Reaction, Scope and limitations. in Organic and Biomolecular Chemistry. 2008;6:4059-4063.
doi:10.1039/B809157A .

Bondžić, Bojan, Eilbracht, Peter, "Syntheses of Tetrahydro-β-Carbolines via Tandem Hydformylation / Pictet-Spengler Reaction, Scope and limitations" in Organic and Biomolecular Chemistry, 6 (2008):4059-4063,
https://doi.org/10.1039/B809157A . .

TY  - JOUR
AU  - Bondžić, Bojan
AU  - Eilbracht, Peter
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6808
AB  - The two component one-pot hydroformylation/Fischer indole synthesis sequence of 2,5 dihydropyrroles and phenyl hydrazines allows a facile and convenient access to tetrahydro-β-carbolines in moderate to good yields.
PB  - American Chemical Society (ACS)
T2  - Organic Letters
T1  - A Novel Access to Tetrahydro β-Carbolines via One-Pot Hydroformylation / Fischer Indole Synthesis: Rearrangement of 3,3- Spiroindoleninium Cations
VL  - 10
IS  - 16
SP  - 3433
EP  - 3436
DO  - 10.1021/ol801071y
ER  - 

@article{
author = "Bondžić, Bojan and Eilbracht, Peter",
year = "2008",
abstract = "The two component one-pot hydroformylation/Fischer indole synthesis sequence of 2,5 dihydropyrroles and phenyl hydrazines allows a facile and convenient access to tetrahydro-β-carbolines in moderate to good yields.",
publisher = "American Chemical Society (ACS)",
journal = "Organic Letters",
title = "A Novel Access to Tetrahydro β-Carbolines via One-Pot Hydroformylation / Fischer Indole Synthesis: Rearrangement of 3,3- Spiroindoleninium Cations",
volume = "10",
number = "16",
pages = "3433-3436",
doi = "10.1021/ol801071y"
}

Bondžić, B.,& Eilbracht, P.. (2008). A Novel Access to Tetrahydro β-Carbolines via One-Pot Hydroformylation / Fischer Indole Synthesis: Rearrangement of 3,3- Spiroindoleninium Cations. in Organic Letters
American Chemical Society (ACS)., 10(16), 3433-3436.
https://doi.org/10.1021/ol801071y

Bondžić B, Eilbracht P. A Novel Access to Tetrahydro β-Carbolines via One-Pot Hydroformylation / Fischer Indole Synthesis: Rearrangement of 3,3- Spiroindoleninium Cations. in Organic Letters. 2008;10(16):3433-3436.
doi:10.1021/ol801071y .

Bondžić, Bojan, Eilbracht, Peter, "A Novel Access to Tetrahydro β-Carbolines via One-Pot Hydroformylation / Fischer Indole Synthesis: Rearrangement of 3,3- Spiroindoleninium Cations" in Organic Letters, 10, no. 16 (2008):3433-3436,
https://doi.org/10.1021/ol801071y . .

TY  - JOUR
AU  - Bondžić, Bojan
AU  - Farwick, Andreas
AU  - Liebich, Jens
AU  - Eilbracht, Peter
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6807
AB  - Combination of enantioselective allylation reactions with a tandem hydroformylation–Fischer indole synthesis sequence as a highly diversity-oriented strategy for the synthesis of tryptamines and homologues was explored. This modular approach allows the substituents at C3 of the indole core, the type of the amine moiety, and the distance of the amine moiety to the indole core in the final synthetic step to be defined. The starting materials required for the hydroformylation step were synthesized viairidium catalyzed enantioselective allylic substitution reactions in high yields and excellent enantioselectivities. The Rh catalyzed hydroformylation step in the presence of phenyl hydrazine, allows the in situ formed aldehyde to be trapped as the hydrazone. Subsequent acid catalyzed indolization furnishes the desired indole structures in moderate to good yields.
PB  - Royal Society of Chemistry
T2  - Organic and Biomolecular Chemistry
T1  - Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis
VL  - 6
SP  - 3723
EP  - 3731
DO  - 10.1039/B809143A
ER  - 

@article{
author = "Bondžić, Bojan and Farwick, Andreas and Liebich, Jens and Eilbracht, Peter",
year = "2008",
abstract = "Combination of enantioselective allylation reactions with a tandem hydroformylation–Fischer indole synthesis sequence as a highly diversity-oriented strategy for the synthesis of tryptamines and homologues was explored. This modular approach allows the substituents at C3 of the indole core, the type of the amine moiety, and the distance of the amine moiety to the indole core in the final synthetic step to be defined. The starting materials required for the hydroformylation step were synthesized viairidium catalyzed enantioselective allylic substitution reactions in high yields and excellent enantioselectivities. The Rh catalyzed hydroformylation step in the presence of phenyl hydrazine, allows the in situ formed aldehyde to be trapped as the hydrazone. Subsequent acid catalyzed indolization furnishes the desired indole structures in moderate to good yields.",
publisher = "Royal Society of Chemistry",
journal = "Organic and Biomolecular Chemistry",
title = "Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis",
volume = "6",
pages = "3723-3731",
doi = "10.1039/B809143A"
}

Bondžić, B., Farwick, A., Liebich, J.,& Eilbracht, P.. (2008). Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis. in Organic and Biomolecular Chemistry
Royal Society of Chemistry., 6, 3723-3731.
https://doi.org/10.1039/B809143A

Bondžić B, Farwick A, Liebich J, Eilbracht P. Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis. in Organic and Biomolecular Chemistry. 2008;6:3723-3731.
doi:10.1039/B809143A .

Bondžić, Bojan, Farwick, Andreas, Liebich, Jens, Eilbracht, Peter, "Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis" in Organic and Biomolecular Chemistry, 6 (2008):3723-3731,
https://doi.org/10.1039/B809143A . .

TY  - JOUR
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Dejan
AU  - Angelovski, Goran
AU  - Lehnig, Manfred
AU  - Eilbracht, Peter
AU  - Tinant, Bernard
AU  - Juranić, Zorica
AU  - Smith, Kirsten S.
AU  - Yang, Young S.
AU  - Diaz, Damaris S.
AU  - Smith, Philip L.
AU  - Milhous, Wilbur K.
AU  - Đoković, Dejan
AU  - Šolaja, Bogdan
PY  - 2006
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3096
AB  - Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4'') methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg, kg(-1), day(-1), and 2/5 mice at 50 mg, kg(-1), day(-1), showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO center dot radicals were detected by EPR experiments. This finding and the indication of Fe(IV)=O species led us to propose that RO center dot radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Tetraoxane antimalarials and their reaction with Fe(II)
VL  - 49
IS  - 13
SP  - 3790
EP  - 3799
DO  - 10.1021/jm050966r
ER  - 

@article{
author = "Opsenica, Igor and Terzić-Jovanović, Nataša and Opsenica, Dejan and Angelovski, Goran and Lehnig, Manfred and Eilbracht, Peter and Tinant, Bernard and Juranić, Zorica and Smith, Kirsten S. and Yang, Young S. and Diaz, Damaris S. and Smith, Philip L. and Milhous, Wilbur K. and Đoković, Dejan and Šolaja, Bogdan",
year = "2006",
abstract = "Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4'') methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg, kg(-1), day(-1), and 2/5 mice at 50 mg, kg(-1), day(-1), showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO center dot radicals were detected by EPR experiments. This finding and the indication of Fe(IV)=O species led us to propose that RO center dot radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Tetraoxane antimalarials and their reaction with Fe(II)",
volume = "49",
number = "13",
pages = "3790-3799",
doi = "10.1021/jm050966r"
}

Opsenica, I., Terzić-Jovanović, N., Opsenica, D., Angelovski, G., Lehnig, M., Eilbracht, P., Tinant, B., Juranić, Z., Smith, K. S., Yang, Y. S., Diaz, D. S., Smith, P. L., Milhous, W. K., Đoković, D.,& Šolaja, B.. (2006). Tetraoxane antimalarials and their reaction with Fe(II). in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 49(13), 3790-3799.
https://doi.org/10.1021/jm050966r

Opsenica I, Terzić-Jovanović N, Opsenica D, Angelovski G, Lehnig M, Eilbracht P, Tinant B, Juranić Z, Smith KS, Yang YS, Diaz DS, Smith PL, Milhous WK, Đoković D, Šolaja B. Tetraoxane antimalarials and their reaction with Fe(II). in Journal of Medicinal Chemistry. 2006;49(13):3790-3799.
doi:10.1021/jm050966r .

Opsenica, Igor, Terzić-Jovanović, Nataša, Opsenica, Dejan, Angelovski, Goran, Lehnig, Manfred, Eilbracht, Peter, Tinant, Bernard, Juranić, Zorica, Smith, Kirsten S., Yang, Young S., Diaz, Damaris S., Smith, Philip L., Milhous, Wilbur K., Đoković, Dejan, Šolaja, Bogdan, "Tetraoxane antimalarials and their reaction with Fe(II)" in Journal of Medicinal Chemistry, 49, no. 13 (2006):3790-3799,
https://doi.org/10.1021/jm050966r . .