749906-87-4

Basic information

• Product Name: ethyl-6-(bromomethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• Synonyms: ethyl-6-(bromomethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• CAS NO: 749906-87-4
• Molecular Weight: 373.634
• Mol File: 749906-87-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ethyl-6-(bromomethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl-6-(bromomethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate(749906-87-4)
• EPA Substance Registry System: ethyl-6-(bromomethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate(749906-87-4)

Safety Data

• Hazardous Substances Data: 749906-87-4(Hazardous Substances Data)

Upstream product

• 141-97-9 ethyl acetoacetate 
• 104-88-1 4-chlorobenzaldehyde 
• 5948-71-0 4-(4-chlorophenyl)-5-(ethoxycarbonyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one 

Downstream Products

• 866340-17-2 C₂₀H₁₉ClN₂O₅S 
• 902277-69-4 ethyl 4-(4-chlorophenyl)-2-oxo-6-(tosylmethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1446846-45-2 ethyl-6-(aminomethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydro pyrimidine-5-carboxylate 

Relevant articles and documents

Design, synthesis, in-vitro thymidine phosphorylase inhibition, in-vivo antiangiogenic and in-silico studies of C-6 substituted dihydropyrimidines

Thymidine phosphorylase (TP) is an angiogenic enzyme. It plays an important role in angiogenesis, tumour growth, invasion and metastasis. In current research work, we study the effect of structural modification of dihydropyrimidine-2-ones (DHPM-2-ones) on TP inhibition. A series of eighteen new derivatives of 3,4-dihydropyrimidone-2-one were designed and synthesized through the structural modification at C-6 position. All these new derivatives were then assessed for in-vitro inhibition of thymidine phosphorylase (TP) from E. coli. Oxadiazole derivatives 4a-e exhibited excellent TP-inhibition at low micromolar concentration levels better than standard drug 7-deazaxanthine (7-DX). Among all these compounds, 4b was found to be the most potent with IC50 = 1.09 ± 0.004 μM. Anti-angiogenesis potential of representative compounds were also studied in a chorioallantoic membrane (CAM) assay. Here again, compound 4b was found to be the potent anti-angiogenesis compound in a CAM assay. Docking studies were also performed with Molecular Operating Environment (MOE) to further analyse the mode of inhibition of these compounds. Binding mode analysis of the most active inhibitors showed that these are well accommodated into the binding site of enzyme though stable hydrogen bonding and hydrophobic interactions.