Studies on Synthesis, Chromatographic Resolution, and Antiinflammatory Activities of Some 2-Thioxo-1,2,3,4-tetrahydropyrimidines and Their Condensed Derivatives

Abstract

In this study, the synthesis of some new 2‐thioxo‐1,2,3,4‐tetrahydropyrimidines and their condensed derivatives, thiazolo[3,2‐α] pyrimidines, are described. The structures of the compounds were confirmed by IR, 1H‐NMR, 13C‐NMR, and mass spectroscopy. The direct high‐performance liquid chromatographic separation of the compounds on derivatized cellulose chiral stationary phases such as cellulose tris(3,5‐dimethylphenylcarbamate) (OD), cellulose tris(4‐methylphenylcarbamate) (OG), and cellulose tris(4‐methylbenzoate) (OJ) was studied. All of the compounds were screened for their antiinflammatory activity and also investigated histopathologically. Compounds 3 and 1a were found to be the most promising antiinflammatory agents in this group.

One-pot three-component synthesis of 4-aryl-3,4-dihydro-pyrimidin-2(1<i>H</i>)-thiones catalyzed by Ni loaded SiO₂

“…The crude product was purified by recrystallization from diethyl ether (solid products) or by chromatography using silica gel and mixtures of hexane/ethyl acetate of increasing polarity. The physical data (mp, IR, 1 H NMR, LCMS) of known compounds were found to be identical with those reported in the literature [20,21]. Some selected product characterization data.…”

“…We studied the possibility to synthesize 4-aryl-3,4-dihydropyrimidin-2(1H)-thiones by the Biginelli reaction using methyl 3-oxopentanoate, aldehydes and thiourea using Ni-SiO 2 as the catalyst (Scheme 1). Here, an efficient and simple method for the synthesis of target compounds is described and the synthesis of some compounds has been reported in our previous studies [20,21].…”

Aqueous phase synthesis of polysubstituted pyrimidines/pyrrolidines catalyzed by β-cyclodextrin

“…Pyrimidine derivatives are versatile building blocks in synthetic organic chemistry and many bioactive molecules [1][2][3][4] with pyrimidine skeleton served as M1 muscarinic receptor agonists for the treatment of Alzheimer's disease [5,6] and human immune deficiency virus (HIV) protease inhibitors [7]. Pyrimidine moiety is an important class of N-containing heterocyclic system [8,9], which exhibits wide spectrum of biological activities such as bactericidal [10], fungicidal [11], analgesic [12], anti-hypertensive [13], antimicrobial [14] and anti-infective properties [15].…”

Synthesis of 6-aryl-N,N-diethyl-4-methyl-2-sulfanylidene-1,2,3,6-tetrahydropyrimidine-5-carboxamides

“…An example of multicomponent reactions is the Biginelli reaction which ensured good results in the synthesis of biologically active pyrimidine derivatives [6][7][8]. Compounds of the pyrimidine series were found to exhibit antihypertensive [9][10][11], antitumor [12,13], anti-inflammatory [14], antioxidant [15][16][17], fungicidal [18], and antimicrobial [19] activity.…”