6312-73-8

Usage

Uses

Used in Pharmaceutical Research:
5-Bromo-6-aminouracil is used as a precursor in the synthesis of various pharmaceuticals and agricultural chemicals, contributing to the development of new drugs and products.
Used in Biochemical Research:
As a valuable tool in biochemical research, 5-Bromo-6-aminouracil is utilized in the study of nucleic acids and their interactions, providing insights into the structure and function of these essential biomolecules.
Used in Antimicrobial Applications:
5-Bromo-6-aminouracil is employed as an antimicrobial agent, demonstrating its effectiveness in inhibiting the growth of various microorganisms and contributing to the development of new antimicrobial agents.
Used in Cancer Treatment Research:
5-Bromo-6-aminouracil has been investigated for its potential use in cancer treatment, as it exhibits the ability to inhibit the growth of tumor cells, offering a promising avenue for the development of novel cancer therapeutics.

InChI:InChI=1/C19H29FN2S/c1-2-3-4-9-14-21-19(23)22(17-11-6-7-12-17)15-16-10-5-8-13-18(16)20/h5,8,10,13,17H,2-4,6-7,9,11-12,14-15H2,1H3,(H,21,23)

Upstream product

• 873-83-6 4-Amino-2,6-dihydroxypyrimidine 
• 1439-10-7 4-amino-5-bromopyrimidine 
• 2240-25-7 6-amino-5-bromo-1H-pyrimidin-2-one 

Downstream Products

• 25507-29-3 6-amino-5-benzylaminopyrimidine-2,4(1H,3H)-dione 
• 89721-62-0 6-amino-5-(2-amino-phenylthio)-2,4(1H,3H)-pyrimidinedione 

Relevant academic research and scientific papers

Fragment Discovery for the Design of Nitrogen Heterocycles as Mycobacterium tuberculosis Dihydrofolate Reductase Inhibitors

Fragment-based drug design was used to identify Mycobacterium tuberculosis (Mtb) dihydrofolate reductase (DHFR) inhibitors. Screening of ligands against the Mtb DHFR enzyme resulted in the identification of multiple fragment hits with IC50 values in the range of 38–90 μM versus Mtb DHFR and minimum inhibitory concentration (MIC) values in the range of 31.5–125 μg/mL. These fragment scaffolds would be useful for anti-tubercular drug design.

Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors

Thymidine phosphorylase (TP) is over-expressed in various tumour types and plays an important role in tumour angiogenesis, growth, invasion and metastasis. The enzymatic activity of TP is required for the angiogenic effect of TP, therefore, inhibitors of TP are of significant interest in cancer chemotherapy. A series of xanthine oxidase (XO) activated prodrugs of known inhibitors of TP have been designed and synthesized with the ultimate intent of improving tumour selectivity and pharmacokinetic characteristics. These prodrugs were not inhibitors of TP, but were selectively oxidized by XO at C-2 and/or C-4 of the uracil ring moiety to generate the desired TP inhibitor. Molecular modelling of both the TP inhibitors and XO-activated prodrugs rationalized their binding in the active site of the human TP crystal structure.

Synthesis and enzymatic evaluation of xanthine oxidase-activated prodrugs based on inhibitors of thymidine phosphorylase

A series of xanthine oxidase-activated prodrugs of known inhibitors of thymidine phosphorylase are described. These prodrugs were oxidised by xanthine oxidase at C-2 and/or C-4 of the uracil ring to generate the desired TP inhibitor. The scheme shows the prodrug of TPI. A series of xanthine oxidase-activated prodrugs of known inhibitors of thymidine phosphorylase has been designed and synthesised to introduce tumour selectivity. These prodrugs were oxidised by xanthine oxidase at C-2 and/or C-4 of the uracil ring to generate the desired TP inhibitor.