31385-63-4

Basic information

• Product Name: (5-BROMO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)ACETIC ACID
• Synonyms: 1-carboxymethyl-5-bromouracil;2-(5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acid
• CAS NO: 31385-63-4
• Molecular Formula: C₆H₅BrN₂O₄
• Molecular Weight: 249.02
• Mol File: 31385-63-4.mol
• Article Data: 14

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.001g/cm³
• Refractive Index: 1.623
• CAS DataBase Reference: (5-BROMO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (5-BROMO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)ACETIC ACID(31385-63-4)
• EPA Substance Registry System: (5-BROMO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)ACETIC ACID(31385-63-4)

Safety Data

• Hazardous Substances Data: 31385-63-4(Hazardous Substances Data)

Usage

Description

(5-BROMO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)ACETIC ACID is a chemical compound with the molecular formula C6H5BrN2O4. It is a derivative of pyrimidine and contains a bromo group, two carbonyl groups, and an acetic acid moiety. (5-BROMO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)ACETIC ACID may have potential applications in medicinal chemistry and pharmaceutical research due to its structural features and potential biological activities. Further studies and research are needed to fully understand the properties and potential uses of this compound.

Uses

Used in Pharmaceutical Research:
(5-BROMO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)ACETIC ACID is used as a research compound for exploring its potential biological activities and applications in the development of new drugs. Its unique structural features may contribute to its interaction with various biological targets, making it a promising candidate for further investigation.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (5-BROMO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)ACETIC ACID is used as a starting material or a building block for the synthesis of more complex molecules with potential therapeutic properties. Its structural diversity and functional groups can be exploited to design and develop novel pharmaceutical agents.

InChI:InChI=1/C6H5BrN2O4/c7-3-1-9(2-4(10)11)6(13)8-5(3)12/h1H,2H2,(H,10,11)(H,8,12,13)

Upstream product

• 51-20-7 5-bromouracil 
• 79-11-8 chloroacetic acid 
• 4113-98-8 1-(ethylcarboxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione 
• 5236-64-6 (2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetic acid butyl ester 
• 4113-97-7 uracilacetic acid 
• 79-08-3 bromoacetic acid 

Relevant articles and documents

Synthesis and antitumor activity of novel substituted uracil-1′(N)-acetic acid ester derivatives of 20(S)-camptothecins

A series of novel substituted uracil-1′(N)-acetic acid esters (6–20) of camptothecins (CPTs) were synthesized by the acylation method. These new compounds were evaluated for in vitro antitumor activity against tumor cell lines, A549, Bel7402, BGC-823, HCT-8 and A2780. In vitro results showed that most of the derivatives exhibited comparable or superior cytotoxicity compare to CPT (1) and topotecan (TPT, 2), with 12 and 13 possessing the best efficacy. Four compounds, 9, 12, 13 and 16, were selected to be evaluated for in vivo antitumor activity against H22, BGC-823 and Bel-7402 in mice. In vivo testing results indicated that 12 and 13 had antitumor activity against mouse liver carcinoma H22close to Paclitaxel and cyclophosphamide. 12 had similar antitumor activity against human gastric carcinoma BGC-823 in nude mice compared to irinotecan (3) and possessed better antitumor activity against human hepatocarcinoma Bel-7402 in nude mice than 2. It is also discovered that 12 showed a similar mechanism but better inhibitory activity on topoisomerase I (Topo I) compared to 2. These findings indicate that 20(S)-O-fluorouracil-1′(N)-acetic acid ester derivative of CPTs, 12, could be developed as an antitumor drug candidate for clinical trial.

Synthesis of novel uracil based 2,5-diaminofurans using multi-component reactions

A simple synthesis of highly functionalized 2,5-diaminofurans based pyrimidine derivatives from 1-(carboxymethyl)uracil via a multi-component reaction is described. The reactive 1:1 intermediate produced from the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates was trapped at room temperature by 1-(carboxymethyl)uracil derivatives to yield polyfunctionalized furan rings in fairly good yields.

Synthetic procedures for peptide nucleic acids

A novel class of compounds, known as peptide nucleic acids, bind complementary ssDNA and RNA strands more strongly than a corresponding DNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.