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Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity

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Abstract
A variety of 2-amino-3-arylpropan-1-ols, anti-2-amino-3-aryl-3-methoxypropan-1-ols and anti-2-amino-1-arylpropan-1,3-diols were prepared selectively through elaboration of trans-4-aryl-3-chloro-beta-lactams. In addition, a number of 2-(azidomethyl)aziridines was converted into novel 2-[(1,2,3-triazol-1-yl)methyl]aziridines by Cu(I)-catalyzed azide-alkyne cycloaddition, followed by microwave-assisted, regioselective ring opening by dialkylamine towards 1-(2,3-diaminopropyl)-1,2,3-triazoles. Although most of these compounds exhibited weak antiplasmodial activity, six representatives showed moderate antiplasmodial activity against both a chloroquine-sensitive and a chloroquine-resistant strain of Plasmodium falciparum with IC(50)-values of <= 25 mu M.
Keywords
antimalarial activity, aminopropanes, aziridines, beta-lactams, ring opening, BETA-LACTAM ANTIBIOTICS, ERYTHROCYTE G-PROTEIN, ASYMMETRIC-SYNTHESIS, BUILDING-BLOCKS, CHIRAL AZIRIDINES, SYNTHON METHOD, DERIVATIVES, REACTIVITY, CHEMISTRY, EPOXIDES

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MLA
D’hooghe, Matthias, Stephanie Vandekerckhove, Karen Mollet, et al. “Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and Evaluation of Their Antimalarial Activity.” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 7 (2011): 1745–1752. Print.
APA
D’hooghe, M., Vandekerckhove, S., Mollet, K., Vervisch, K., Dekeukeleire, S., Lehoucq, L., Lategan, C., et al. (2011). Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 7, 1745–1752.
Chicago author-date
D’hooghe, Matthias, Stephanie Vandekerckhove, Karen Mollet, Karel Vervisch, Stijn Dekeukeleire, Liesbeth Lehoucq, Carmen Lategan, Peter J Smith, Kelly Chibale, and Norbert De Kimpe. 2011. “Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and Evaluation of Their Antimalarial Activity.” Beilstein Journal of Organic Chemistry 7: 1745–1752.
Chicago author-date (all authors)
D’hooghe, Matthias, Stephanie Vandekerckhove, Karen Mollet, Karel Vervisch, Stijn Dekeukeleire, Liesbeth Lehoucq, Carmen Lategan, Peter J Smith, Kelly Chibale, and Norbert De Kimpe. 2011. “Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and Evaluation of Their Antimalarial Activity.” Beilstein Journal of Organic Chemistry 7: 1745–1752.
Vancouver
1.
D’hooghe M, Vandekerckhove S, Mollet K, Vervisch K, Dekeukeleire S, Lehoucq L, et al. Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2011;7:1745–52.
IEEE
[1]
M. D’hooghe et al., “Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity,” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 7, pp. 1745–1752, 2011.
@article{1988675,
  abstract     = {A variety of 2-amino-3-arylpropan-1-ols, anti-2-amino-3-aryl-3-methoxypropan-1-ols and anti-2-amino-1-arylpropan-1,3-diols were prepared selectively through elaboration of trans-4-aryl-3-chloro-beta-lactams. In addition, a number of 2-(azidomethyl)aziridines was converted into novel 2-[(1,2,3-triazol-1-yl)methyl]aziridines by Cu(I)-catalyzed azide-alkyne cycloaddition, followed by microwave-assisted, regioselective ring opening by dialkylamine towards 1-(2,3-diaminopropyl)-1,2,3-triazoles. Although most of these compounds exhibited weak antiplasmodial activity, six representatives showed moderate antiplasmodial activity against both a chloroquine-sensitive and a chloroquine-resistant strain of Plasmodium falciparum with IC(50)-values of <= 25 mu M.},
  author       = {D'hooghe, Matthias and Vandekerckhove, Stephanie and Mollet, Karen and Vervisch, Karel and Dekeukeleire, Stijn and Lehoucq, Liesbeth and Lategan, Carmen and Smith, Peter J and Chibale, Kelly  and De Kimpe, Norbert},
  issn         = {1860-5397},
  journal      = {BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {antimalarial activity,aminopropanes,aziridines,beta-lactams,ring opening,BETA-LACTAM ANTIBIOTICS,ERYTHROCYTE G-PROTEIN,ASYMMETRIC-SYNTHESIS,BUILDING-BLOCKS,CHIRAL AZIRIDINES,SYNTHON METHOD,DERIVATIVES,REACTIVITY,CHEMISTRY,EPOXIDES},
  language     = {eng},
  pages        = {1745--1752},
  title        = {Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity},
  url          = {http://dx.doi.org/10.3762/bjoc.7.205},
  volume       = {7},
  year         = {2011},
}

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