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Synthesis and antiplasmodial evaluation of aziridine-(iso)quinoline hybrids and their ring-opening products

Stephanie Vandekerckhove, Sofie De Moor, Dries Segers UGent, Carmen de Kock, Peter J Smith, Kelly Chibale, Norbert De Kimpe UGent and Matthias D'hooghe UGent (2013) MEDCHEMCOMM. 4(4). p.724-730
abstract
Aziridine-(iso)quinoline hybrid systems were prepared as novel synthetic intermediates en route to functionalized (iso)quinolines with potential antimalarial activity. Various quinolinecarboxaldehydes were converted into quinoline-aziridine-pyrazole, -pyridazinone or -pyrimidinone hybrids, and the three-membered azaheterocyclic moiety in these compounds was finally subjected to ring opening by either methanol or water to provide the corresponding functionalized quinolines. In addition, 5-hydroxyisoquinoline was used for the preparation of isoquinoline-aziridine chimeras, which were further transformed into a variety of functionalized isoquinolines via regioselective aziridine ring opening by various nucleophiles. Antiplasmodial evaluation of these new aziridine-(iso)quinoline hybrids and their ring-opening products revealed micromolar potency (0.22-30 mu M) for all representatives against a chloroquine-sensitive strain of the malaria parasite Plasmodium falciparum. The six most potent compounds also showed micromolar activity against a chloroquine-resistant strain of P. falciparum with IC50-values ranging between 1.02 and 17.58 mu M.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
isoquinoline hybrids, ANTIMALARIAL ACTIVITY, antimalarial agents, quinoline hybrids, CHIRAL AZIRIDINES, AGENTS, MOLECULES, DESIGN, ASSAY, 2-(CYANOMETHYL)AZIRIDINES, CHEMOTHERAPY, PROPRANOLOL, DERIVATIVES
journal title
MEDCHEMCOMM
MedChemComm
volume
4
issue
4
pages
724 - 730
Web of Science type
Article
Web of Science id
000316868900014
JCR category
CHEMISTRY, MEDICINAL
JCR impact factor
2.626 (2013)
JCR rank
26/58 (2013)
JCR quartile
2 (2013)
ISSN
2040-2503
DOI
10.1039/c3md20377h
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
4238284
handle
http://hdl.handle.net/1854/LU-4238284
date created
2014-01-21 08:58:23
date last changed
2016-12-19 15:37:56
@article{4238284,
  abstract     = {Aziridine-(iso)quinoline hybrid systems were prepared as novel synthetic intermediates en route to functionalized (iso)quinolines with potential antimalarial activity. Various quinolinecarboxaldehydes were converted into quinoline-aziridine-pyrazole, -pyridazinone or -pyrimidinone hybrids, and the three-membered azaheterocyclic moiety in these compounds was finally subjected to ring opening by either methanol or water to provide the corresponding functionalized quinolines. In addition, 5-hydroxyisoquinoline was used for the preparation of isoquinoline-aziridine chimeras, which were further transformed into a variety of functionalized isoquinolines via regioselective aziridine ring opening by various nucleophiles. Antiplasmodial evaluation of these new aziridine-(iso)quinoline hybrids and their ring-opening products revealed micromolar potency (0.22-30 mu M) for all representatives against a chloroquine-sensitive strain of the malaria parasite Plasmodium falciparum. The six most potent compounds also showed micromolar activity against a chloroquine-resistant strain of P. falciparum with IC50-values ranging between 1.02 and 17.58 mu M.},
  author       = {Vandekerckhove, Stephanie and De Moor, Sofie and Segers, Dries and de Kock, Carmen and Smith, Peter J and Chibale, Kelly and De Kimpe, Norbert and D'hooghe, Matthias},
  issn         = {2040-2503},
  journal      = {MEDCHEMCOMM},
  keyword      = {isoquinoline hybrids,ANTIMALARIAL ACTIVITY,antimalarial agents,quinoline hybrids,CHIRAL AZIRIDINES,AGENTS,MOLECULES,DESIGN,ASSAY,2-(CYANOMETHYL)AZIRIDINES,CHEMOTHERAPY,PROPRANOLOL,DERIVATIVES},
  language     = {eng},
  number       = {4},
  pages        = {724--730},
  title        = {Synthesis and antiplasmodial evaluation of aziridine-(iso)quinoline hybrids and their ring-opening products},
  url          = {http://dx.doi.org/10.1039/c3md20377h},
  volume       = {4},
  year         = {2013},
}

Chicago
Vandekerckhove, Stephanie, Sofie De Moor, Dries Segers, Carmen de Kock, Peter J Smith, Kelly Chibale, Norbert De Kimpe, and Matthias D’hooghe. 2013. “Synthesis and Antiplasmodial Evaluation of Aziridine-(iso)quinoline Hybrids and Their Ring-opening Products.” Medchemcomm 4 (4): 724–730.
APA
Vandekerckhove, S., De Moor, S., Segers, D., de Kock, C., Smith, P. J., Chibale, K., De Kimpe, N., et al. (2013). Synthesis and antiplasmodial evaluation of aziridine-(iso)quinoline hybrids and their ring-opening products. MEDCHEMCOMM, 4(4), 724–730.
Vancouver
1.
Vandekerckhove S, De Moor S, Segers D, de Kock C, Smith PJ, Chibale K, et al. Synthesis and antiplasmodial evaluation of aziridine-(iso)quinoline hybrids and their ring-opening products. MEDCHEMCOMM. 2013;4(4):724–30.
MLA
Vandekerckhove, Stephanie, Sofie De Moor, Dries Segers, et al. “Synthesis and Antiplasmodial Evaluation of Aziridine-(iso)quinoline Hybrids and Their Ring-opening Products.” MEDCHEMCOMM 4.4 (2013): 724–730. Print.