154146-07-3

Basic information

• Product Name: CHEMBRDG-BB 5157250
• Synonyms: CHEMBRDG-BB 5157250;2-AMINO-5-PHENYL-4,6-PYRIMIDINEDIOL;2-amino-5-phenyl-4,6-pyrimidinediol(SALTDATA: FREE);2-Amino-5-phenylpyrimidine-4,6-diol
• CAS NO: 154146-07-3
• Molecular Formula: C₁₀H₉N₃O₂
• Molecular Weight: 203.2
• Mol File: 154146-07-3.mol

Chemical Properties

• Boiling Point: 493.7°C at 760 mmHg
• Flash Point: 252.4°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 2.27E-10mmHg at 25°C
• Refractive Index: 1.703
• CAS DataBase Reference: CHEMBRDG-BB 5157250(CAS DataBase Reference)
• NIST Chemistry Reference: CHEMBRDG-BB 5157250(154146-07-3)
• EPA Substance Registry System: CHEMBRDG-BB 5157250(154146-07-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 154146-07-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H9N3O2/c11-10-12-8(14)7(9(15)13-10)6-4-2-1-3-5-6/h1-5H,(H4,11,12,13,14,15)

Upstream product

• 50-01-1 guanidine hydrochloride 
• 83-13-6 diethyl 2-phenylmalonate 

Downstream Products

• 65004-49-1 4,6-dichloro-5-phenylpyrimidin-2-amine 
• 1395343-07-3 4,6-dichloro-2-{[(dimethylamino)methylene]amino}-5-phenylpyrimidine 

Relevant articles and documents

5-substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4, 6-dichloropyrimidines: Synthesis and inhibitory effects on immune-activated nitric oxide production

A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino- 4,6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4,6- dichloropyrimidine with an IC50 of 2 μM (higher activity than the most potent reference compound) while the IC50s of other derivatives were within the range of 9-36 l M. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.

5-Substituted 2-amino-4, 6-dihydroxypyrimidines and 2-amino-4, 6-dichloropyrimidines: Synthesis and inhibitory effects on immune-activated nitric oxide production

A series of 5-substituted 2-amino-4, 6-dihydr-oxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4, 6-dihydroxypyrimi-dine analogs to novel 5-substituted 2-amino-4, 6-dichloro-pyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino-4, 6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4, 6-dichloropyrimidine with an IC50 of 2 lM (higher activity than the most potent reference compound) while the IC50s of other derivatives were within the range of 9-36 μM. The 2-amino-4, 6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.

PYRIMIDINE COMPOUNDS INHIBITING THE FORMATION OF NITRIC OXIDE AND PROSTAGLANDIN E2, METHOD OF PRODUCTION THEREOF AND USE THEREOF

The invention provides pyrimidine compounds of general formula (I), which reduce simultaneously the production of nitric oxide (NO) and prostaglandin E2 (PGE2). They have no negative effect on the viability of cells in concentrations decreasing the production of these factors by up to 50%; they are not cytotoxic. Furthermore, a method of preparation of the pyrimidine compounds of general formula (I), carrying 2-formamido group, a pharmaceutical composition comprising the substituted pyrimidine compounds according to the invention, and the use of these compounds for the treatment of inflammatory and cancer diseases are provided.˙