Synthesis, Characterization Of Thiazolidin-4-one, Oxazolidin-4-one And Imidazolidin-4-one Derivatives From 6-Amino-1, 3-dimethyluraciland Evaluation Of Their Antioxidant And Antimicrobial Agent

Abstract

In this study, a new series of 6-amino-1,3-dimethyluracil derivative with 6-(3-substituted N-benzylidene)-1,3-dimethyl pyrimidine-2,4-dione-6-yl derivatives which were synthesized by using one pot synthesis. The reaction of 6-amino-1,3-dimethyluracil and different aromatic aldehyde in ethanol yielded Schiff bases (1-6). In the subsequent step reaction of Schiff bases )1-6) with 2-mercaptoacetic acid, 2-chloroacetic acid and 2-amino acetic acidn in Tetrahydrofuran yielded five membered heterocyclic rings of 6-amino-1,3-dimethyluracil derivative which includes: 2,3-thiazolidin-4-one (7-12), 2,3-oxazolidin-5-one (13-18), 2,3-imidazolidin-4-one (19-24) derivatives. The structures of newly synthesized compounds were confirmed by their physicochemical and spectral means FTIR, 1HNMR and 13CNMR. The synthesized compounds were evaluated in vitro for antioxidant and antimicrobial activities against four types of bacteria and four types of fungi

Synthesis, identification of some new tetrazoline, thiazolidin-4-one and imidazolidin-4-one derivatives and evaluation anticancer of their molecular docking and anti-oxidant experimental

“…of 2-mercaptoacetic acid were added dropwise to THF (10 mL). After that, the reaction mixture was heated to reflux temperature (20)(21)(22)(23)(24). The mixture was filtered, washed, and purified further with ethanol to recrystallization.…”

“…Table 4. the physical properties as well as the FTIR spectral data cm-1 of the compounds that were produced (16)(17)(18)(19)(20).…”

“…as a result of their ease of synthesis, uracil derivatives are regarded as promising compounds in drug discovery. The pyrimidine core is an important pharmacophore moiety of biologically active natural and synthetic compounds that compete for the same binding sites [15] the most conmen biological activities of uracil derivatives in the last years application Antioxidan t [2], Anti-flamatory [16], Anticaner [17], Anti-leukemia [18], Antibacterial [19,20], anti-tumour [21], anti-angiogenesis [22] and Anti-diabetic [23].…”

Utility of 6-Aminouracils for Building Substituted and Heteroannulated Pyrimidines: A Comprehensive Review

“…Due to the presence of free amino group and activated CH group (C-5 position) in 6-aminouracils nuclei, they act as excellent nucleophiles and therefore the more common reactions are the condensation with aldehydes as well as electrophilic substitution reactions. The chemical reactivity of 6-amino-1,3dimethyluracil (1) towards aldehydic compounds proceeds in different ways because minor articles described the condensation reactions occurred between the amino group in compound 1 with the aldehydic function, [21][22][23][24] while major articles reported the condensation occurred between C-5 in compound 1 with the aldehyde groups. [25][26][27][28][29][30] Many authors support the condensation occurred at C-5 due to the electron repelling mesomeric effect of the amino group which enhances the nucleophilicity of C-5 and therefore induced the nucleophilic attack at the aldehyde carbon.…”

“…The nucleophilic condensation reactions of 6-amino-1,3-dimethyluracil (1) with various aromatic aldehyde 2, in absolute ethanol in the presence of glacial acetic acid as catalyst, provided 6-(benzylideneamino)-1,3dimethylpyrimidine-2,4-dione derivatives 3 which have antibacterial and antioxidant activity (Scheme 1). 21 Scheme 1…”