5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)methyl]-6-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

Abstract

5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)-methyl]-6-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 3 was synthesized via a multicomponent reaction. The Aldol-Michael addition reactions of N,N-dimethylbarbituric acid, cyclohexane-1,3-dione, and 3-fluorobenzaldehyde in aqueous solution gave the product in high yield. The molecular structure of the compound was confirmed by spectroscopic methods and X-ray crystallography. The title compound (C 19 H 19 FN 2 O 5 •H 2 O) crystallizes in the Monoclinic form, P2 1 /c, a = 7.8630 (5) Å,

Enamine Barbiturates and Thiobarbiturates as a New Class of Bacterial Urease Inhibitors

“…In the present study, urease was preincubated with the inhibitors for a period of 15 min, which proved to be sufficient in our studies. In this context, and as a continuation of our extended medicinal chemistry program based on the barbituric and thiobarbituric acid moieties [30,[33][34][35][36][37][38][39][40][41][42][43][44], here we examined the in vitro anti-urease activity of a collection of 1,3-dimethylbarbiturate-enamine compounds and their analogs, thiobarbiturate derivatives. In addition, molecular docking studies were performed to evaluate the molecular interactions of the newly synthesized compounds with selected drug targets (PDB ID 4GY7).…”