Work

Synthesis and biological screening of diethyl [N-(thiazol-2-yl)carbamoyl]methylphosphonates

Year: 2018

Type: article

Abstract: A three-step synthesis, involving condensation of bromomethyl aryl ketones with urea to afford 2aminothiazoles, 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 4carboxythiazole analogue 3g was obtained by selective hydrolysis of the corresponding ethyl ester 3f.The phosphonate esters exhibited significant anti-cancer activity (nM -low µM IC 50 values) against SH-SY5Y cells and, in one case, 7.6 µM MIC90 anti-TB activity against the virulent M. tuberculosis H 37 Rv strain; the chloroacetamido precursors all exhibited some antimalarial (PfLDH) activity, three with IC 50 values in the range 1.0 -8.9 µΜ.

Source: ARKIVOC

DOI: 10.24820/ark.5550190.p010.534