dc.contributor.author |
Olawode, Emmanuel O.
|
|
dc.contributor.author |
Tandlich, Roman
|
|
dc.contributor.author |
Prinsloo, Earl
|
|
dc.contributor.author |
Isaacs, Michelle
|
|
dc.contributor.author |
Hoppe, Heinrich C.
|
|
dc.contributor.author |
Seldon, Ronnett
|
|
dc.contributor.author |
Warner, Digby F.
|
|
dc.contributor.author |
Steenkamp, Vanessa
|
|
dc.contributor.author |
Kaye, Perry T.
|
|
dc.date.accessioned |
2019-10-17T07:22:01Z |
|
dc.date.available |
2019-10-17T07:22:01Z |
|
dc.date.issued |
2018-09-09 |
|
dc.description.abstract |
A three-step synthesis, involving condensation of bromomethyl aryl ketones with urea to afford 2- aminothiazoles, their chloroacetylation and subsequent solvent-free Arbuzov phosphonation has afforded a series of novel diethyl [N-(thiazol-2-yl)carbamoyl]methylphosphonates 3a-3f in good overall yields; the 4- carboxythiazole analogue 3g was obtained by selective hydrolysis of the corresponding ethyl ester 3f. The phosphonate esters exhibited significant anti-cancer activity (nM - low μM IC50 values) against SH-SY5Y cells and, in one case, 7.6 μM MIC90 anti-TB activity against the virulent M. tuberculosis H37Rv strain; the chloroacetamido precursors all exhibited some antimalarial (PfLDH) activity, three with IC50 values in the range 1.0 - 8.9 μM. |
en_ZA |
dc.description.department |
Pharmacology |
en_ZA |
dc.description.sponsorship |
Rhodes University for financial support and a bursary (E.O.O.) and the South African
Medical Research Council (SAMRC) for support with funds from National Treasury under its Economic
Competitiveness and Support Package. |
en_ZA |
dc.description.uri |
http://www.arkat-usa.org |
en_ZA |
dc.identifier.citation |
Olawode, E.O., Tandlich, R., Prinsloo, E., et al. 2018, 'Synthesis and biological screening of diethyl [N-(thiazol-2-yl)carbamoyl]methylphosphonates', Arkivoc, part vii, pp. 110-118. |
en_ZA |
dc.identifier.issn |
1551-7004 (online) |
|
dc.identifier.issn |
1551-7012 (print) |
|
dc.identifier.other |
10.24820/ark.5550190.p010.534 |
|
dc.identifier.uri |
http://hdl.handle.net/2263/71874 |
|
dc.language.iso |
en |
en_ZA |
dc.publisher |
ARKAT |
en_ZA |
dc.rights |
©2018 ARKAT-USA, Inc. Published with a Creative Commons Attribution Non-Commercial License. |
en_ZA |
dc.subject |
2-(2-Chloroacetamido)thiazoles |
en_ZA |
dc.subject |
N-(thiazol-2-yl)carbamoyl]methylphosphonates |
en_ZA |
dc.subject |
Synthesis |
en_ZA |
dc.subject |
Biological activities |
en_ZA |
dc.subject |
Isoprenoid biosynthesis |
en_ZA |
dc.subject |
Aryl |
en_ZA |
dc.subject |
Acid |
en_ZA |
dc.subject |
Derivatives |
en_ZA |
dc.subject |
Binding |
en_ZA |
dc.subject |
Local anesthetics |
en_ZA |
dc.title |
Synthesis and biological screening of diethyl [N-(thiazol-2-yl)carbamoyl]methylphosphonates |
en_ZA |
dc.type |
Article |
en_ZA |