36946-75-5Relevant academic research and scientific papers
Design, Synthesis, Molecular Docking, and Evaluation Antioxidant and Antimicrobial Activities for Novel 3-Phenylimidazolidin-4-One and 2-Aminothiazol-4-One Derivatives
Abdellattif, Magda H.,Assy, Mohamed G.,Aziz, Maged A.,Elhoseni, Nourhan Kh. R.,Hamed, Eman O.,Shehab, Wesam S.
, (2022/01/31)
On our way to discovering and developing compounds that have an antioxidant impact compared to ascorbic acid and other biological activities, we designed, synthesized, and evaluated a new series of heterocyclic moieties drugs (1–11) as antioxidants and antimicrobial agents. As starting moieties, these new candidates were derived from two promising heterocyclic compounds, imidazoldin-4-one and thiazol-4-one. Firstly, diphenylimidazol 1 was obtained because of the cyclo condensation one-pot ternary reaction of urea, aniline, and chloroacetic acid under thermal conditions. Out of this starting compound, we could design and create new vital rings such as purine and triazine as in compounds 5 and 6, respectively. Secondly, the start thiazole derivative 7 was obtained from the intermolecular cyclization of thiourea, chloroacetic acid, p-nitobezaldehyde in the presence of sodium acetate. We synthesized various derivatives from this second starting compound 7 by being subjected to different reagents such as aniline, phenylenediamine, phenylhydrazine, and barbituric acid to yield 8, 9, 10, and 11, respectively. Using ascorbic acid as the standard compound, the pharmacological testing for antioxidant activity assessment of the produced derivatives was evaluated against ABTS (2,20-azinobis (3-ethylbenzothiazoline-6-sulfonic acid). Candidate 6 exhibited the best activity as an antioxidant agent compared to ascorbic acid as a reference compound. Moreover, all compounds were evaluated as antimicrobial agents against a series of bacteria and fungi. Among all synthesized compounds, compound 6 achieved high efficiency against two types of fungi and four kinds of bacteria, as Clotrimazole and Ampicillin were used as the reference agents, respectively. All chemical structures of the novel synthesized candidates were unequivocally elucidated and confirmed utilizing spectroscopical and elemental investigations.
A facile synthesis of 5-arylidene-2-imino-4-thiazolidinones under microwave irradiation
Zhou, Jian-Feng,Sun, Xiao-Jun,Zhu, Feng-Xia,Li, Yan-Lun,Gong, Gui-Xia
experimental part, p. 4182 - 4187 (2009/04/11)
A series of 5-arylidene-2-imino-4-thiazolidinone derivatives were synthesized by the cross-aldol condensation of aromatic aldehydes with 2-imino-4-thiazolidinone in sodium acetate/acetic acid under microwave irradiation. The reactions were completed in 10 min with 63-91% yields, were environmental benign, and had easy workup. Copyright Taylor & Francis Group, LLC.
Heterophase N-aminomethylation of 5-arylidenepseudothiohydantoins by arylamines and aqueous formaldehyde in aromatic solvents: Effect of substituents in the heterocyclic substrate and the aryl amine on the efficiency of the process
Ramsh,Medvedskiy,Uryupov
, p. 948 - 954 (2008/03/12)
We have obtained a series of 3-aryl-7-arylidene-3,4-dihydro-2H-[1,3] thiazolo[3,2-a][1,3,5]triazin-6(7H)-ones by means of heterophase aminomethylation of 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones with aqueous formaldehyde and aromatic amines in benzene or toluene. We explain the effect of substituents in the heterocyclic substrate and the aryl amine on the efficiency of the process within a detailed scheme for one of the possible aminomethylation reaction routes.
STRUCTURE OF 2-IMINO-5-ARYLIDENE-4-THIAZOLIDINONES
Ramsh, S. M.,Solov'eva, S. Yu.,Ginak, A. I.
, p. 611 - 614 (2007/10/02)
It was established by means of PMR spectroscopy that, depending on the method of preparation, 2-imino-5-arylidene-4-thiazolidones exist in the form of various geometrical isomers relative to the exocyclic C=N bond.The E isomers are obtained as a result of condensation of 2-imino-4-thiazolidone with the corresponding benzaldehydes, whereas the Z isomers are formed in the solvolysis of hydroxymethyl and piperidinomethyl derivatives.The geometrical isomers retain their individuality in solutions in d6-DMSO and in ethanol.Upon dissolving in alkali with subsequent neutralization the E isomer of 2-imino-5-benzylidene-4-thiazolidinone is converted to the Z isomer.Reverse conversion of the Z isomer to the E isomer occurs when a solid sample is heated to 180 deg C.
