60750-37-0

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,4-Tetrahydro-6-methyl-2-oxo-4-phenyl-5-pyrimidinecarboxylic acid is used as a potential pharmaceutical agent for its possible medicinal properties. Its unique structural features, including the methyl and phenyl groups, suggest that it could be utilized in the development of new drugs or therapeutic agents. However, further research and development are necessary to fully understand and harness its potential applications in this field.

Upstream product

• 123237-03-6 ethyl 6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate 
• 188780-24-7 5-methoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one 
• 674-82-8 4-methyleneoxetan-2-one 
• 100-52-7 benzaldehyde 
• 57-13-6 urea 
• 2440-60-0 2-methyl-isourea 
• 60750-23-4 benzyl 6-methyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 100-51-6 benzyl alcohol 
• 541-50-4 2-acetoacetic acid 

Downstream Products

• 30570-16-2 6-methyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidine 
• 1442442-64-9 C₁₉H₁₈N₂O₄ 
• 1442442-75-2 C₂₀H₂₁N₃O₃ 
• 1314801-55-2 N-cyclohexyl-4-phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide 
• 1250832-26-8 C₁₁H₁₁IN₂O 
• 1250832-25-7 C₁₁H₁₁BrN₂O 

Relevant academic research and scientific papers

One pot synthesis of micromolar BACE-1 inhibitors based on the Dihydropyrimidinone scaffold and their Thia and Imino analogues

A library of dihydropyrimidinones was synthesized via a “one-pot” three component Biginelli reaction using different aldehydes in combination with β-dicarbonyl compounds and urea. Selected 2-thiooxo and 2-imino analogs were also obtained with the Biginell

Pyrimidines as block units in heterocycles: novel synthesis of pyrimidines and condensed pyrimidine derivatives

Compound 1 condensed with benzaldehyde to produce styryl pyrimidine 2. Pyridopyrimidines 5, 8 and 10 resulted from [4 + 2] cycloaddition (condensation) of 1 with malononitrile, ethyl cyanoacetate and/or ethyl acetoacetate. Compound 1 was also concerted to

Design, Synthesis, and Anti-HIV-1 Evaluation of a Novel Series of 1,2,3,4-Tetrahydropyrimidine-5-Carboxylic Acid Derivatives

A series of tetrahydropyrimidine derivatives (2a – 2l) were designed, synthesized, and screened for anti-HIV-1 properties based on the structures of HIV-1 gp41 binding site inhibitors, NB-2 and NB-64. A computational study was performed to predict the pharmacodynamics, pharmacokinetics, and drug-likeness features of the studied molecules. Docking studies revealed that the carboxylic acid group in the molecules forms salt bridges with either Lys574 or Arg579. Physiochemical properties (e.g., molecular weight, number of hydrogen bond donors, number of hydrogen bond acceptors, and number of rotatable bonds) of the synthesized compounds confirmed and exhibited that these compounds were within the range set by Lipinski's rule of five. Compounds 2e and 2k with 4-chlorophenyl substituent and 4-methylphenyl group at C(4) position of the tetrahydropyrimidine ring was the most potent one among the tested compounds. This suggests that these compounds may serve as leads for development of novel small-molecule HIV-1 inhibitors.

Synthesis method of 3,4-dihydropyrimidin-2-ketone compounds catalyzed by ionic liquid at room temperature

The present invention discloses a synthesis method of 3,4-dihydropyrimidin-2-ketone compounds catalyzed by ionic liquid at room temperature. Key technology is as follows: nano-silicon-loaded bronsted acid functional group ionic liquid is used as a catalys

Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions

The Biginelli reaction was combined with the Passerini reaction for the first time in a sequential multicomponent tandem reaction approach. After evaluation of all possible linker components and a suitable solvent system, highly functionalized dihydropyrimidone-α-acyloxycarboxamide compounds were obtained in good to excellent yields. In a first reaction step, different 3,4-dihydropyrimidin-2(1H)-one acids were synthesized, isolated and fully characterized. These products were subsequently used in a Passerini reaction utilizing a dichloromethane/dimethyl sulfoxide solvent mixture. By variation of the components in both multicomponent reactions, a large number of structurally diverse compounds could be synthesized. In addition, a one-pot Biginelli-Passerini tandem reaction was demonstrated. All products were carefully characterized via 1D and 2D NMR as well as IR and HRMS.

DIHYDROPYRIMIDIN-2(1H)-ONES AND DIHYDROPYRIMIDIN-2(1H)-THIONES AS INHIBITORS OF SODIUM IODIDE SYMPORTER

The invention relates to novel dihydropyrimidin-2(lH)-ones and dihydropyrimidin- 2(lH)-thiones of formula (la). The invention also relates to the use of such compounds as medicaments, and in particular as inhibitors of sodium iodide symporter (NIS) and reducers of iodine transport and/or accumulation into NIS expressing cells. The invention also concerns a pharmaceutical composition comprising at least one compound of formula (la) as active principle.

Dihydropyrimidin-2(1H)-ones and dihydropyrimidin-2(1H)-thiones as inhibitors of sodium iodide symporter

The invention relates to novel dihydropyrimidin-2(1H)-ones and dihydropyrimidin-2(1H)-thiones of formula (I): for use as medicaments, and in particular as inhibitors of sodium iodide symporter (NIS) and reducers of iodine transport and/or accumulation into NIS-expressing cells. The invention also relates to a pharmaceutical composition comprising at least one compound of formula (I) as active principle. Finally, the present invention relates to specific dihydropyrimidin-2(1H)-ones and dihydropyrimidin-2(1H)-thiones of formula (I) as such.

Synthesis and Evaluation of 3,4-Dihydropyrimidin-2(1H)-ones as Sodium Iodide Symporter Inhibitors

The sodium iodide symporter (NIS) is responsible for the accumulation of iodide in the thyroid gland. This transport process is involved in numerous thyroid dysfunctions and is the basis for human contamination in the case of exposure to radioactive iodine species. 4-Aryl-3,4-dihydropyrimidin-2(1H)-ones were recently discovered by high-throughput screening as the first NIS inhibitors. Described herein are the synthesis and evaluation of 115 derivatives with structural modifications at five key positions on the pyrimidone core. This study provides extensive structure-activity relationships for this new class of inhibitors that will serve as a basis for further development of compounds with invivo efficacy and adequate pharmacokinetic properties. In addition, the SAR investigation provided a more potent compound, which exhibits an IC50 value of 3.2nM in a rat thyroid cell line (FRTL5).

6 - METHYL - 4 - PHENYL - 5 - ( PHENYL OR CYCLOALKYL) CARBAMOYL - 1,2,3, 4 - TETRAHYDROPYRIMIDIN- 2 - ONE DERIVATIVES AS ANTITUBERCULAR AGENTS

The present invention discloses antitubercular compounds selected from tetrahydropyrimidones/ tetrahydrothiopyrimidone derivatives of Formula (1) and its pharmaceutically acceptable salts for the treatment of Mycobacterium in the dormant phase. Formula (1) wherein, R is H, halogen, dihalogen, O-alkyl, di- O-alkyl, R1 is phenyl, chlorophenyl, nitrophenyl, diclorophenyl, cycloalkyl, preferably cyclohexyl, X is O or S.

Synthesis and Suzuki-Miyaura reactions of 5-halo-3,4-dihydropyrimidin-2(1H) -ones

A novel synthesis of 6-methyl-4-phenyl-5-substituted-3,4-dihydropyrimidin- 2(1H)-ones from 6-methyl-4-phenyl-5-halo-3,4-dihydropyrimidin-2(1H)-ones via the Suzuki-Miyaura reaction is reported. These previously unknown heterocyclic halides are easily prepared using the Biginelli multicomponent reaction followed by halodecarboxylation. The effect of varied substitution at the C-4 position on the cross-coupling reaction is also examined.