60750-23-4

Upstream product

• 5396-89-4 benzyl acetoacetate 
• 100-52-7 benzaldehyde 
• 57-13-6 urea 
• 123237-03-6 ethyl 6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 60750-37-0 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-phenylpyrimidine-5-carboxylic acid 
• 1442442-75-2 C₂₀H₂₁N₃O₃ 
• 1442442-64-9 C₁₉H₁₈N₂O₄ 

Relevant academic research and scientific papers

Synthesis and catalytic application of D-glucose derived ytterbium(III) complex in Biginelli reaction

4,6-O-Ethylidene-N-(2-hydroxybenzylidene)-β-D-glucopyranosylamine has been reacted with ytterbium(III) acetate and the resultant complex has been used as catalyst in the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones (DHPMs). Twenty-one DHPMs have been synthesised under neat reaction condition in appreciable yields (73–96percent) and reusability of the catalyst has been established.

Synthesis, biological evaluation and molecular docking study of dihydropyrimidine derivatives as potential anticancer agents

A series of dihydropyrimidine analogues were prepared via one-pot Biginelli three-component condensation reaction and characterized by NMR, FT-IR, MS spectra, and element analysis. Subsequently, they were screened for in vitro anticancer effect. These analogues revealed good cytotoxic activity against three human cancer cell lines including MCF-7, HepG-2, and A549. Among these analogues, compounds 4d and 4h were the most potent against three cell lines. Cell viability assays indicated 4a and 4c had lower cytotoxicity. In vitro cytotoxicity study on all synthesized compounds demonstrated that introduction of electron withdrawing substituents on C4 position of phenyl ring of dihydropyrimidine contributed to the antiproliferative potency. Moreover, in silico molecular docking results stipulated a sign of good correlation between experimental activity and calculated binding affinity. It proved 4d and 4h as the strongest compounds. Binding modes of analogues proposed the involvement of hydrophobic interactions and hydrogen bonds with Eg5 active site. Structure activity relationship studies indicated that incorporating electron withdrawing substituents on C4 position of phenyl ring of dihydropyrimidine are important for this biological activity.

Evaluation of alcohols as substrates for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under environmentally friendly conditions

The aim of this research was to develop a procedure for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under environmentally friendly conditions using alcohols as the starting materials in aqueous media. The developed protocol resulted in 3,4-dihydropyrimidin-2(1H)-ones derivatives, which are relevant intermediates with therapeutic and pharmacological properties. Target products were synthetized in a tandem process, which meets the requirements of pharmaceutical chemistry. The influence of the reaction conditions was investigated, and as a result, various substituted 3,4-dihydropyrimidin-2(1H)-ones were obtained with a yield of up to 81percent, free from heavy metal impurities.

A Bifunctional Metal/Acid Catalyst for One-pot Multistep Synthesis of Pharmaceuticals

Abstract: One inhibitor of the fatty acid transporter FATP4 was synthesized in a three steps one-pot process in the presence of a bifunctional metal/acid catalyst. This molecule which has potential interest for the treatment of the obesity in orlistat (Xenical TM) analogue-based therapies has a 3,4-dihydropyrimidin-2(1H)-one (DHPM) scaffold and was obtained by means of a three one-pot process through successive oxidation, cyclocondensation and transesterification reactions. The one-pot strategy was extended to the synthesis of a series of related ester DHPM derivatives.

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 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.

Targeting dormant tuberculosis bacilli: Results for molecules with a novel pyrimidone scaffold

Our inability to completely control TB has been due in part to the presence of dormant mycobacteria. This also renders drug regimens ineffective and is the prime cause of the appearance of drug-resistant strains. In continuation of our efforts to develop novel antitubercular agents that especially target dormant mycobacteria, a set of 55 new compounds belonging to the pyrimidone class were designed on the basis of CoMFA and CoMSIA studies, and these were synthesized and subsequently tested against both the dormant and virulent BCG strain of M. tuberculosis. Some novel compounds have been identified which selectively inhibit the dormant tuberculosis bacilli with significantly low IC50 values. This study reports the second molecule after TMC-207, having the ability to inhibit tuberculosis bacilli exclusively in its dormant phase. The synthesis was accomplished by a modified multicomponent Biginelli reaction. A classification model was generated using the binary QSAR approach - recursive partitioning (RP) to identify structural characteristics related to the activity. Physicochemical, structural, topological, connectivity indices, and E-state key descriptors were used for generation of the decision tree. The decision tree could provide insights into structure-activity relationships that will guide the design of more potent inhibitors. This paper reports the second molecule after TMC-207, with the ability to inhibit tuberculosis bacilli in its dormant phase. The paper reports molecules with a novel Pyrimidone Scaffold, the synthesis of which was accomplished with a modified multi-component Biginelli reaction. A classification model was generated using recursive partitioning (RP) technique to identify structural characteristics of the molecules with their varying activities.

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.

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.

Efficient, stable, and reusable Lewis acid-surfactant-combined catalyst: One-pot Biginelli and solvent-free esterification reactions

Cerium(III) trislaurylsulfonate (Ce(LS)3), a Lewis acid and surfactant combined catalyst, was prepared and characterized by SEM, SEM-EDX, XRD, NMR, FT-IR, TG, and elemental analysis. Ce(LS)3 was found to be stable and efficient to catalyze one-pot Biginelli and solvent-free esterification reactions. Furthermore, Ce(LS)3 is easy to recycle after reaction by pouring into cold water and filtration. Present work will shed deep insight into the understanding of the catalytic nature of LASCs, and extend its application in important organic transformations.