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

Simple item page
dc.contributor.authorD’hooghe, Matthias
dc.contributor.authorVandekerckhove, Stéphanie
dc.contributor.authorMollet, Karen
dc.contributor.authorVervisch, Karel
dc.contributor.authorDekeukeleire, Stijn
dc.contributor.authorLehoucq, Liesbeth
dc.contributor.authorLategan, Carmen
dc.contributor.authorSmith, Peter J
dc.contributor.authorChibale, Kelly
dc.contributor.authorDe Kimpe, Norbert
dc.date.accessioned2021-10-08T06:20:12Z
dc.date.available2021-10-08T06:20:12Z
dc.date.issued2011
dc.description.abstractA 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-β-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 IC50-values of ≤25 μM.
dc.identifier.apacitation, Vandekerckhove, S., Mollet, K., Vervisch, K., Dekeukeleire, S., Lehoucq, L., ... De Kimpe, N. (2011). Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity. <i>Beilstein Journal of Organic Chemistry</i>, 7(4), 1745 - 1752. http://hdl.handle.net/11427/34221en_ZA
dc.identifier.chicagocitation, Stéphanie Vandekerckhove, Karen Mollet, Karel Vervisch, Stijn Dekeukeleire, Liesbeth Lehoucq, Carmen Lategan, Peter J Smith, Kelly Chibale, and Norbert De Kimpe "Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity." <i>Beilstein Journal of Organic Chemistry</i> 7, 4. (2011): 1745 - 1752. http://hdl.handle.net/11427/34221en_ZA
dc.identifier.citation, Vandekerckhove, S., Mollet, K., Vervisch, K., Dekeukeleire, S., Lehoucq, L., Lategan, C. & Smith, P.J. 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. <i>Beilstein Journal of Organic Chemistry.</i> 7(4):1745 - 1752. http://hdl.handle.net/11427/34221en_ZA
dc.identifier.issn1860-5397
dc.identifier.issn2195-951X
dc.identifier.ris TY - Journal Article AU - D’hooghe, Matthias AU - Vandekerckhove, Stéphanie AU - Mollet, Karen AU - Vervisch, Karel AU - Dekeukeleire, Stijn AU - Lehoucq, Liesbeth AU - Lategan, Carmen AU - Smith, Peter J AU - Chibale, Kelly AU - De Kimpe, Norbert AB - 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-β-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 IC50-values of ≤25 μM. DA - 2011 DB - OpenUCT DP - University of Cape Town IS - 4 J1 - Beilstein Journal of Organic Chemistry LK - https://open.uct.ac.za PY - 2011 SM - 1860-5397 SM - 2195-951X T1 - Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity TI - Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity UR - http://hdl.handle.net/11427/34221 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/34221
dc.identifier.vancouvercitation, 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(4):1745 - 1752. http://hdl.handle.net/11427/34221.en_ZA
dc.language.isoeng
dc.publisher.departmentDepartment of Chemistry
dc.publisher.facultyFaculty of Science
dc.sourceBeilstein Journal of Organic Chemistry
dc.source.journalissue4
dc.source.journalvolume7
dc.source.pagination1745 - 1752
dc.source.urihttps://dx.doi.org/10.3762/bjoc.7.205
dc.subject.otherChemistry
dc.subject.otherantimalarial activity
dc.subject.otheraminopropanes
dc.subject.otheraziridines
dc.subject.otherbeta-lactams
dc.subject.otherring opening
dc.subject.otherBETA-LACTAM ANTIBIOTICS
dc.subject.otherERYTHROCYTE G-PROTEIN
dc.subject.otherASYMMETRIC-SYNTHESIS
dc.subject.otherBUILDING-BLOCKS
dc.subject.otherCHIRAL AZIRIDINES
dc.subject.otherSYNTHON METHOD
dc.subject.otherDERIVATIVES
dc.subject.otherREACTIVITY
dc.subject.otherCHEMISTRY
dc.subject.otherEPOXIDES
dc.titleSynthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity
dc.typeJournal Article
uct.type.publicationResearch
uct.type.resourceJournal Article
Files
Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
DhoogheMatthias_Synthesis2_amin_2011.pdf
Size:
318.18 KB
Format:
Adobe Portable Document Format
Description:
Download
Collections
Journal Articles