18337-64-9

Basic information

• Product Name: 4(1H)-Pyrimidinone, 6-hydroxy-5-phenyl-
• Synonyms: 4(1H)-Pyrimidinone, 6-hydroxy-5-phenyl-;5-phenylpyrimidine-4,6-diol
• CAS NO: 18337-64-9
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.18
• Mol File: 18337-64-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 373-375 °C (decomp)
• Appearance: /
• Density: 1.33±0.1 g/cm3(Predicted)
• PKA: 5.30±0.10(Predicted)
• CAS DataBase Reference: 4(1H)-Pyrimidinone, 6-hydroxy-5-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(1H)-Pyrimidinone, 6-hydroxy-5-phenyl-(18337-64-9)
• EPA Substance Registry System: 4(1H)-Pyrimidinone, 6-hydroxy-5-phenyl-(18337-64-9)

Safety Data

• Hazardous Substances Data: 18337-64-9(Hazardous Substances Data)

Usage

General Description

4(1H)-Pyrimidinone, 6-hydroxy-5-phenyl- is a chemical compound with the molecular formula C10H8N2O2. It is a heterocyclic organic compound that contains a pyrimidine ring structure with a hydroxyl group at the 6th position and a phenyl group at the 5th position. This chemical compound is often used in the pharmaceutical and agricultural industries as a building block for the synthesis of various compounds with potential biological activities. It has been studied for its potential use in the development of new drugs or agrochemicals due to its diverse reactivity and pharmacological properties. Additionally, it has also been investigated for its potential antimicrobial, antiviral, and anticancer activities.

Upstream product

• 3473-63-0 formamidine acetic acid 
• 83-13-6 diethyl 2-phenylmalonate 
• 10255-95-5 2-phenylmalonamide 
• 109-94-4 formic acid ethyl ester 
• 37434-59-6 dimethyl 2-phenylmalonate 
• 6313-33-3 formamidine hydrochloride 
• 101-41-7 benzeneacetic acid methyl ester 
• 103-82-2 phenylacetic acid 
• 77287-34-4 formamide 

Downstream Products

• 3974-16-1 4,6-dichloro-5-phenyl-pyrimidine 
• 926008-65-3 [4-(6-chloro-5-phenylpyrimidin-4-ylethynyl)phenyl]dimethylamine 
• 885948-54-9 1-[(2-acetoxyethoxy)methyl]-4-hydroxy-5-phenylpyrimidin-6(1H)-one 
• 1240108-41-1 4,6-dibromo-5-phenyl-pyrimidine 
• 441797-36-0 C₁₇H₁₅ClN₄O₂S 
• 1393813-57-4 C₂₃H₂₁BrN₆O₄S 

Relevant articles and documents

The discovery of N -[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy] ethoxy]-4-pyrimidinyl]- N ′-propylsulfamide (macitentan), an orally active, potent dual endothelin receptor antagonist

Starting from the structure of bosentan (1), we embarked on a medicinal chemistry program aiming at the identification of novel potent dual endothelin receptor antagonists with high oral efficacy. This led to the discovery of a novel series of alkyl sulfamide substituted pyrimidines. Among these, compound 17 (macitentan, ACT-064992) emerged as particularly interesting as it is a potent inhibitor of ETA with significant affinity for the ET B receptor and shows excellent pharmacokinetic properties and high in vivo efficacy in hypertensive Dahl salt-sensitive rats. Compound 17 successfully completed a long-term phase III clinical trial for pulmonary arterial hypertension.

4-Amino-5-aryl-6-arylethynylpyrimidines: Structure-activity relationships of non-nucleoside adenosine kinase inhibitors

A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT-702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-ylpyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed.

Triazolopyrimidine cannabinoid receptor 1 antagonists

The present application describes compounds according to both Formulas I and II, pharmaceutical compositions comprising at least one compound according to either Formula I or II and optionally one or more additional therapeutic agents, and methods of treatment using the compounds according to Formulas I and II both alone and in combination with one or more additional therapeutic agents. The compounds have the following general formulas: including all prodrugs, solvates, pharmaceutically acceptable salts and stereoisomers, wherein R1, R2, R3, R4 and R5 are described herein.