144405-50-5

Basic information

• Product Name: N(3)-phenacyluridine
• Synonyms: N(3)-phenacyluridine
• CAS NO: 144405-50-5
• Molecular Formula: C₁₇H₁₈N₂O₇
• Molecular Weight: 362.336
• Mol File: 144405-50-5.mol

Chemical Properties

• Boiling Point: 633.8°Cat760mmHg
• Flash Point: 337.1°C
• Appearance: /
• Density: 1.523g/cm³
• Vapor Pressure: 6.21E-17mmHg at 25°C
• Refractive Index: 1.654
• CAS DataBase Reference: N(3)-phenacyluridine(CAS DataBase Reference)
• NIST Chemistry Reference: N(3)-phenacyluridine(144405-50-5)
• EPA Substance Registry System: N(3)-phenacyluridine(144405-50-5)

Safety Data

• Hazardous Substances Data: 144405-50-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H18N2O7/c20-9-12-14(23)15(24)16(26-12)18-7-6-13(22)19(17(18)25)8-11(21)10-4-2-1-3-5-10/h1-7,12,14-16,20,23-24H,8-9H2/t12-,14-,15-,16-/m1/s1

Upstream product

• 70-11-1 α-bromoacetophenone 
• 58-96-8 uridine 
• 532-27-4 1-chloroacetophenone 

Relevant articles and documents

Structural modifications of UMP, UDP, and UTP leading to subtype-selective agonists for P2Y2, P2Y4, and P2Y6 receptors

A large series of derivatives and analogues of the uracil nucleotides UMP, UDP, and UTP with modifications in various positions of the uracil moiety and/or the phosphate groups were synthesized and evaluated at human P2Y2, P2Y4, and P2Y6 receptors. 2-(Ar)alkylthio substitution of UMP and UDP was best tolerated by the P2Y2 receptor. 2-Phenethylthio-UMP (13e) showed an EC50 value of 1.3 μM at P2Y2 and >70-fold selectivity versus P2Y4 and P2Y 6 receptors. Substitution of the 2-keto group in UMP by NH (13g, iso-CMP) resulted in the first potent and selective P2Y4 agonist (EC50 4.98 μM, >20-fold selective vs P2Y2 and P2Y6). In contrast, replacement of the 2-keto function in UDP by NH yielded a potent P2Y2 agonist (12g, iso-CDP, EC50 = 0.604 μM, >100-fold selective). In an attempt to obtain metabolically stable UTP analogues, β,γ-dichloro- and β,γ-difluoro-methylene-UTP derivatives were synthesized. The triphosphate modifications were much better tolerated by P2Y2, and in some cases also by P2Y6, than by P2Y4 receptors. 4-Thio-β,γ-difluoromethylene-UTP (14g) was a potent P2Y2 agonist with an EC50 value of 0.134 μM and >50-fold selectivity. N3-Phenacyl-β,γ-dichloromethylene- UTP (14b) proved to be a potent P2Y6 receptor agonist (EC 50 0.142 μM) with high selectivity versus P2Y4 (50-fold) and moderate selectivity versus P2Y2 receptors (6-fold).

Synthesis and structure-activity relationships of uracil nucleotide derivatives and analogues as agonists at human P2Y2, P2Y4, and P2Y6 receptors

A series of UTP, UDP, and UMP derivatives and analogues were synthesized and evaluated at the human pyrimidinergic P2Y receptor subtypes P2Y2, P2Y4, and P2Y6 stably expressed in 1321N1 astrocytoma cells. Substituents at N3