102233-94-3

Basic information

• Product Name: N,N'-1,3-bisphenylmethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
• Synonyms: N,N'-1,3-bisphenylmethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
• CAS NO: 102233-94-3
• Molecular Weight: 280.37
• Mol File: 102233-94-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N,N'-1,3-bisphenylmethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-1,3-bisphenylmethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone(102233-94-3)
• EPA Substance Registry System: N,N'-1,3-bisphenylmethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone(102233-94-3)

Safety Data

• Hazardous Substances Data: 102233-94-3(Hazardous Substances Data)

Upstream product

• 1852-17-1 3,4,5,6-tetrahydropyrimidin-2(1H)-one 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 124-38-9 carbon dioxide 
• 10239-34-6 N,N'-dibenzyl-1,3-diaminopropane 

Downstream Products

• 23458-59-5 N,N'-1,3-bisphenylmethyl-1,2,3,4,5,6-hexahydropyrimidine 

Relevant articles and documents

Novel bis-arylalkylamines as myeloperoxidase inhibitors: Design, synthesis, and structure-activity relationship study

Human myeloperoxidase (MPO) plays an important role in innate immunity but also aggravates tissue damage by oxidation of biomolecules at sites of inflammation. As a result from a recent high-throughput virtual screening approach for MPO inhibitors, bis-2,2′-[(dihydro-1,3(2H,4H) pyrimidinediyl)bis(methylene)]phenol was detected as a promising lead compound for inhibition of the MPO-typical two-electron oxidation of chloride to hypochlorous acid (IC50= 0.5 μM). In the present pharmacomodulation study, 37 derivatives of this lead compound were designed and synthesized driven by comprehensive docking studies and the impact on the chlorination activity of MPO. We describe the structural requirements for optimum (i) binding to the heme periphery and (ii) inhibition capacity. Finally, the best three inhibitors (bis-arylalkylamine derivatives) were probed for interaction with the MPO redox intermediates Compound I and Compound II. Determined apparent bimolecular rate constants together with determination of reduction potential and nucleophilicity of the selected compounds allowed us to propose a mechanism of inhibition. The best inhibitor was found to promote the accumulation of inactive form of MPO-Compound II and has IC50= 54 nM, demonstrating the successful approach of the drug design. Due to the similarity of ligand interactions between MPO and serotonine transporter, the selectivity of this inhibitor was also tested on the serotonin transporter providing a selectivity index of 14 (KiSERT/IC50MPO).

Carbon dioxide as a carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas: Scope and limitations

Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such as SOCl2, TsCl, or AcCl. The intramolecular trapping of the activated carbamate by a hydroxyl group leads to the formation of 2-oxazolidinones or 2-oxazinones in good to excellent yields. This methodology was successfully applied to the synthesis of cyclic ureas up to 7-membered rings from the corresponding diamines.