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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

Matthias D'hooghe UGent, Stephanie Vandekerckhove UGent, Karen Mollet UGent, Karel Vervisch UGent, Stijn Dekeukeleire UGent, Liesbeth Lehoucq UGent, Carmen Lategan, Peter J Smith, Kelly Chibale and Norbert De Kimpe UGent (2011) BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 7. p.1745-1752
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
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
journal title
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Beilstein J. Org. Chem.
volume
7
pages
1745 - 1752
Web of Science type
Article
Web of Science id
000298638400001
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
2.517 (2011)
JCR rank
22/56 (2011)
JCR quartile
2 (2011)
ISSN
1860-5397
DOI
10.3762/bjoc.7.205
language
English
UGent publication?
yes
classification
A1
copyright statement
I have retained and own the full copyright for this publication
id
1988675
handle
http://hdl.handle.net/1854/LU-1988675
date created
2012-01-17 09:32:21
date last changed
2012-09-28 13:47:28
@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 {\textlangle}= 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},
  keyword      = {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},
}

Chicago
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.
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.
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.
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.