Olawode, Emmanuel O.Tandlich, RomanPrinsloo, EarlIsaacs, MichelleHoppe, Heinrich C.Seldon, RonnettWarner, Digby F.Steenkamp, VanessaKaye, Perry T.2019-10-172019-10-172018-09-09Olawode, 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. 110-118.1551-7004 (online)1551-7012 (print)10.24820/ark.5550190.p010.534http://hdl.handle.net/2263/71874A 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©2018 ARKAT-USA, Inc. Published with a Creative Commons Attribution Non-Commercial License.2-(2-Chloroacetamido)thiazolesN-(thiazol-2-yl)carbamoyl]methylphosphonatesSynthesisBiological activitiesIsoprenoid biosynthesisArylAcidDerivativesBindingLocal anestheticsArticle