31385-63-4

Usage

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 
• 79-08-3 bromoacetic acid 
• 4113-97-7 uracilacetic acid 
• 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 

Relevant academic research and scientific papers

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 and DNA/RNA complementation studies of peptide nucleic acids containing 5-halouracils

The monomers of peptide nucleic acids containing 5-halouracils (5-XU-PNA), incorporated into heptameric PNA in the middle position, have been synthesized. Thermodynamic analyses revealed that the heptameric PNA oligomer with DNA and RNA showed higher duplex stability compared to the unmodified PNA counterpart. NMR studies suggested that the electron withdrawing effect of the halogen atom increased the strength of the XU-A hydrogen bond.

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.

Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility

A novel class of compounds known as peptide nucleic acids, bind complementary DNA and RNA strands, and generally do so more strongly than the corresponding DNA or RNA strands while exhibiting increased sequence specificity and solubility. The peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases, including 2,6-diaminopurine, attached to a polyamide backbone, and contain alkyl amine side chains.

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.

Peptide nucleic acids having 2,6-diaminopurine nucleobases

A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than a corresponding DNA strand, and exhibit increased sequence specificity and binding affinity. The peptide nucleic acids of the invention comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone. Some PNAs of the invention also contain C1-C8alkylamine side chains.

Linked peptide nucleic acids

Novel peptide nucleic acids and novel linked peptide nucleic acids, form triple stranded structures with nucleic acids. The peptide nucleic acids include ligands such as naturally occurring nucleobases attached to the peptide backbone through a suitable linker. Other nucleobases including C-pyrimidines and iso-pyrimidines can be used as the ligands in Hoogsteen strands to increase binding affinity. Two peptide nucleic acid strands are joined together with a linker to form a bis-peptide nucleic acid. The individual strands of the peptide nucleic acids in the bis compounds can be oriented either parallel or antiparallel to each other.

Peptide nucleic acids

Novel peptide nucleic acids and novel linked peptide nucleic acids, form triple stranded structures with nucleic acids. The peptide nucleic acids include ligands such as naturally occurring nucleobases attached to a peptide backbone through a suitable linker. Other nucleobases including C-pyrimidines and iso-pyrimidines can be used as the ligands in Hoogsteen strands to increase binding affinity. Two peptide nucleic acid strands are joined together with a linker to form a bis-peptide nucleic acid. The individual strands of the peptide nucleic acids in the bis compounds can be orientated either parallel or antiparallel to each other.

Double-stranded peptide nucleic acids

A novel class of compounds, known as peptide nucleic acids, form double-stranded structures with one another and with ssDNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.

Synthesis and hybridization properties of DNA-PNA chimeras carrying 5- bromouracil and 5-methylcytosine

The preparation of 5-bromouracil and 5-methylcytosine peptide nucleic acid (PNA) monomers is described. These PNA monomers were used for the preparation of several DNA-PNA chimeras and their hybridization properties are described. The substitution of cyto