ChemInform Abstract: Graphite Catalyzed Solvent Free Synthesis of Dihydropyrimidin-2(1H)-ones/thiones and Their Antidiabetic Activity (original) (raw)
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Bioorganic & medicinal chemistry letters, 2014
A solvent free three component condensation reaction between an aldehyde, ethyl acetoacetate and urea catalyzed by graphite, a green catalyst is described for the synthesis of dihydropyrimidin-2(1H)-ones. This protocol is scalable and the catalyst is reusable. This method is also applied for the synthesis of dihydropyrimidin-2(1H)-thiones. α-Amylase, a key enzyme in carbohydrate metabolism is generally targeted for management of type 2 diabetes. The therapeutic potential of the dihydropyrimidinones and dihydropyrimidinthiones to inhibit α-amylase activity was evaluated by in vitro assay. Of the synthesized compounds 3,4-dihydropyrimidin-2(1H)-thione (1k) demonstrated highest inhibition of α-amylase activity.
Frontiers in Endocrinology
In an attempt to find new targets for α-amylase and α-glucosidase for the treatment of type 2 diabetes mellitus, the present study aims in determining the anti-diabetic potential of synthesized dihydropyrimidinone derivatives. The in vitro α-glucosidase and α-amylase inhibitory activity was performed and the molecular docking analysis of the ligand in the active binding site of target protein was determined. The results revealed significant percent inhibition of α-glucosidase by the compound 6-benzyl-4-(4-hydroxyphenyl)-3,4,6,7-tetrahydro-1H-pyrrolo[3,4-d]pyrimidine-2,5-dione (compound A). The active compound showed 81.99% inhibition when compared to standard ascorbic acid having percent inhibition 81.18%. The IC50 of active compound (A) showed to be 1.02 µg/ml. The molecular docking analysis revealed that the ligand bound to the active binding site of protein with the lowest binding energy of -7.9 kcal/mol that was also significantly similar to standard having -7.8 kcal/mol binding...
Synthesis of 3, 4-Dihydropyrimidin-2 (1H)-Ones and Their
2012
Trichloroacetic acid was found to be a convenient catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and their corresponding 2(1H)-thiones through a one-pot three-component reaction of aldehydes, alkyl acetoacetate, and urea or thiourea at 70°C under solvent-free conditions.
Journal of Heterocyclic Chemistry, 2015
in Wiley Online Library (wileyonlinelibrary.com). 2-Thioxo/oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives 2a-d were prepared by the reaction of ethyl acetoacetate and thiourea or urea with aldehydes using NH 4 Cl as a catalyst. Compounds 2a and 2c reacted with mono and bihalogenated compounds such as ethyl iodide, chloroacetonitrile, epichlorohydrin, acetyl chloride, ethyl bromoacetate, chloroacetic acid, chloroacetylchloride, and/or oxalyl chloride to afford compounds 3-9 and 10, respectively. Compounds 2a, 2c, and 7 were allowed to react with p-fluorobenzaldehyde to yield the corresponding products 11a, 11b, and 12, respectively. Oxidation of 2a and 2c gave 2b, 13-16 dependent on the oxidizing agent used. Vilsmeiere-Haack formylation of 2a and 2b with POCl 3 /DMF afforded 17a and 17b. Chlorination of 2b and 2d gave the chlorinated derivative 18a and 18b, which reacted with thiourea to give thioureidopyrimidine 19a and 19b. Reactions of 2a with hydrazine monohydrate, semicarbazide hydrochloride, and sodium hydroxide gave compounds 20-22, respectively. The cytotoxicity and in vitro anticancer evaluation of some prepared compounds have been assessed against two different human tumor cell lines including breast adenocarcinoma MCF-7 and human hepatocellular carcinoma HepG2. Antimicrobial and antioxidant activities of some compounds were investigated. The newly synthesized compounds were characterized by IR, 1 H-NMR, 13 C-NMR, and mass spectral data.
Chemistry, anti-diabetic activity and structural analysis of substituted dihydropyrimidine analogues
Journal of Molecular Structure, 2021
In an effort to identify an anti-diabetic agent, a series of methyl/ethyl 4-(hydroxyphenyl)-6-methyl-2oxo/thioxo-1,2,3,4 tetrahydropyrimidine-5-carboxylate analogues (4a-h) have been synthesized, purified, and characterized by using Fourier-Transform Infrared Spectroscopy (FT-IR) and NMR (1 H and 13 C). The synthesized compounds were screened for anti-hyperglycemic activity using Streptozotocin (STZ) induced diabetic rat model. The anti-hyperglycemic activity of dihydropyrimidine (DHPM) compound is mainly analyzed with the variation of substituents present on the phenyl ring and urea/thiourea group on pharmacophoric features. Further, the crystal structure and supramolecular characteristics of two compounds 4c and 4f were analyzed through a single-crystal X-ray method and the Hirshfeld Surface Analysis, which shows hydrogen bonding through N-H •••O and N-H •••S interactions with the formation of ring motif in the crystal structure. It is interesting to note that among the title compounds, the 4a, 4e, 4f, and 4g significantly displayed a better hypoglycemic effect in vivo rat model study.
Research Journal of Chemistry and Environment, 2022
Four new Ni(II) complexes of general formula [Ni(H 2-Qtsc-R) 2 ](NO 3) 2 (H 2-Qtsc-R ¼ 4N-substituted thiosemicarbazones of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde, where R ¼ H (1), Me (2), Et (3), or Ph (4)) have been synthesized and characterized. The geometry of the complexes was confirmed by single crystal X-ray crystallography for one of the complexes (3). The binding affinity of the complexes with DNA and protein have been studied which indicate that they could interact with calf thymus DNA and bovine serum albumin protein. Investigations of antioxidative properties showed that all the complexes have strong radical scavenging properties. Cytotoxic studies showed that the complexes exhibited effective cytotoxic activity against a panel of human cancer cells without affecting the normal cells much.
MILD ACIDIC CHARCOAL CATALYZED SYNTHESIS OF 3,4-DIHYDROPYRIMIDIN-2(1H)-ONE/-THIONE DERIVATIVES
Chemistry Journal of Moldova, 2022
A mild catalyst system with comparative reduction in amount of catalyst was demonstrated. The multicomponent synthesis of 3,4-dihydropyrimidin-2(1H)-ones and-thiones using acetic acid supported on activated charcoal as a mild acid catalyst in ethanol under both conventional as well as microwave irradiation conditions has been achieved. The obtained catalyst system is more efficient under microwave irradiation than under conventional conditions with shorter reaction times (3-9 min) and excellent yields (78-94 %).
An efficient bakers’ yeast catalyzed synthesis of 3,4-dihydropyrimidin-2-(1H)-ones
Tetrahedron Letters, 2007
Pyrimidine derivatives R 0510 An Efficient Bakers' Yeast Catalyzed Synthesis of 3,4-Dihydropyrimidin-2-(1H)-ones.-Fermenting bakers' yeast provides a good catalytic medium for the synthesis of various dihydropyrimidine derivatives via Biginelli-type three-component coupling of aldehydes, acetoacetates and urea derivatives. Interestingly, when 2-hydroxybenzaldehyde is used, a tricyclic product (VIII) is obtained instead of the expected dihydropyrimidinone.-(KUMAR*, A.;