2950-93-8

Basic information

• Product Name: ethyl 4-(5-amino-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)butanoate
• CAS NO: 2950-93-8
• Molecular Formula: C₁₀H₁₅N₃O₄
• Molecular Weight: 241.2438
• Mol File: 2950-93-8.mol
• Article Data: 1

Chemical Properties

• Density: 1.253g/cm³
• Refractive Index: 1.518
• CAS DataBase Reference: ethyl 4-(5-amino-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-(5-amino-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)butanoate(2950-93-8)
• EPA Substance Registry System: ethyl 4-(5-amino-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)butanoate(2950-93-8)

Safety Data

• Hazardous Substances Data: 2950-93-8(Hazardous Substances Data)

Upstream product

• 2969-81-5 Ethyl 4-bromobutyrate 
• 2950-89-2 ethyl ω-N1-[5-nitro-2,4-(1H,3H)pyrimidinedione]butanoate 

Downstream Products

• 148-09-4 4-(5--3,4-dihydro-2,4-dioxo-1(2H)-pyrimidin)-buttersaeure 

Relevant articles and documents

Design, synthesis, and biological activity of hybrid compounds between uramustine and DNA minor groove binder distamycin A

The design, synthesis, characterization, DNA binding properties, and cytotoxic activity of a novel series of hybrids, namely, a molecular combination of the natural antibiotic distamycin A and the antineoplastic agent uramustine, are reported, and the structure-activity relationships are discussed. This homologous series 29-34 consisted of the minor groove binder distamycin A joined to uramustine (uracil mustard) by suitable aliphatic carboxylic acid moieties containing a flexible polymethylene chain that is variable in length [(CH2)n, where n = 1-6). All the hybrid compounds in this series exhibit enhanced activity compared to both distamycin A and uramustine derivatives 22-27 used for conjugation, giving IC50 values in the range 7.26-0.07 μM following a 1 h exposure of human leukemic K562 cells, with maximal activity shown when n = 6. The distance between the uramustine and distamycin frame is crucial for the cytotoxicity, with compounds having linker lengths of four to six being at least 20-fold more cytotoxic than liker lengths one to three. Taq polymerase stop experiments demonstrated selective covalent binding of uramustine-distamycin hybrids to A/T rich DNA sequences, which was again more efficent with compounds 32-34 with a longer linker length. Two consequences can be derived from our study: (a) the distamycin moiety directs binding to the minor groove of A/T rich DNA sequences and, consequently, is responsible for the alkylation regioselectivity found in footprinting studies; (b) the higher flexibility due to a longer linker between the distamycin and uracil moieties allows the formation of complexes with the mustard moiety situated more deeply in the minor groove and, hence, with better alkylating properties.