1007-99-4

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-4-CHLORO-6-HYDROXY-5-NITROPYRIMIDINE is used as an antibacterial agent for its ability to inhibit the growth and reproduction of bacteria. This makes it a common ingredient in antimicrobial formulations, contributing to the development of medicines and healthcare products designed to combat bacterial infections.
Used in Drug Development:
Due to its structure and properties, 2-AMINO-4-CHLORO-6-HYDROXY-5-NITROPYRIMIDINE serves as a valuable tool in the research and development of new drugs and medicines targeting bacterial infections. Its unique chemical composition allows for the exploration of its potential in creating novel therapeutic agents.

InChI:InChI=1/C4H3ClN4O3/c5-2-1(9(11)12)3(10)8-4(6)7-2/h1H,(H2,6,8,10)

Upstream product

• 1194-21-4 6-chloroisocytosine 
• 1194-21-4 2-amino-6-chloro-1H-pyrimidin-4-one 
• 1194-21-4 2-amino-6-chloro-4-pyrimidinol 

Downstream Products

• 1123800-12-3 2-amino-5-nitro-6-phenylsulfanyl-1H-pyrimidin-4-one 
• 883-10-3 2-amino-6-(2'-hydroxyethyl)amino-5-nitropyrimidin-4(3H)-one 
• 77903-11-8 α-<(2-Amino-4-hydroxy-5-nitropyrimidin-6-yl)thio>propiophenone 
• 115787-62-7 2-amino-α-cyano-1,6-dihydro-5-nitro-6-oxo-α-(phenylmethyl)-4-pyrimidineacetic acid ethyl ester 
• 126062-18-8 (+/-)-9-<(1β,2α,3β)-2,3-bis(hydroxymethyl)-1-cyclobutyl>guanine 
• 98510-45-3 2-amino-5-nitro-6-<(4-phenylbutyl)amino>pyrimidin-4(3H)-one 
• 141213-93-6 2-amino-6--5-nitro-4(3H)-pyrimidinone 
• 112698-39-2 2-amino-6--5-nitro-4(3H)-pyrimidinone 
• 80466-52-0 2-amino-6-amino-5-nitropyrimidin-4(3H)-one 
• 112698-42-7 2-amino-6--5-nitro-4(3H)-pyrimidinone 
• 33344-07-9 2-amino-5-nitro-6-<(2-oxo-2-phenylethyl)amino>-4(3H)-pyrimidinone 
• 113697-97-5 2-Amino-5-nitro-6-(2-oxo-4-phenyl-butylamino)-3H-pyrimidin-4-one 
• 112698-44-9 2-amino-6--5-nitro-4(3H)-pyrimidinone 
• 114113-85-8 2-amino-6-(4,4-diethoxy-3-hydroxypentylamino)-5-nitropyrimidin-4(3H)-one 

Relevant academic research and scientific papers

Syntheses of 2-amino-4,6-dichloro-5-nitropyrimidine and 2-amino-4,5,6-trichloropyrimidine: an unusual aromatic substitution

2-Amino-4,6-dichloro-5-nitropyrimidine is an intermediate required for the preparation of nitropyrimidines as inactivators of the DNA repairing protein MGMT. When attempting its synthesis, 2-amino-4,5,6-trichloropyrimidine is obtained instead, via unusual aromatic substitution of the nitro group in 2-amino-4-hydroxy-5-nitropyrimidin-6-one by chloride. The synthesis, the reactivity of 4,5,6-trichloropyrimidine and the efficient preparation of 2-amino-4,6-dichloro-5-nitropyrimidine are presented.

Synthesis and structure-activity relationships of guanine analogues as phosphodiesterase 7 (PDE7) inhibitors

The synthesis of a novel series of guanine analogues is reported. The compounds have been assessed in vitro and some analogues have been found to be inhibitors of phosphodiesterase type 7 (PDE7).

Diaminomethyleneaminocarbonyldinitromethane, formed during the preparation of 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone by nitration of 2-amino-6-chloro-4(3H)-pyrimidinone

Difficulties in the nitration of 2-amino-6-chloro-4(3H)-pyrimidinone to give the widely used heterocyclic precursor 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone are shown to be due to formation of an unusual open-chain gem-dinitro compound, identified as diaminomethyleneaminocarbonyldinitromethane. The latter is also formed by the nitration of 2-amino-4,6(3H,5H)-pyrimidinedione. It decomposes with loss of carbon dioxide in dimethyl sulfoxide, or in aqueous potassium hydroxide, to give guanidine and dinitromethane.

SOLID-PHASE SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING N6-(2-DEOXY-ALPHA,BETA-DERYTHROPENTOFURANOSYL)-2,6-DIAMINO-4-HYDROXY-5-FORMAMIDOPYRIMIDINE (Fapy.dG)

A strategy using reverse phosphoramidites for synthesizing oligonucleotides containing Fapy.dG is disclosed.

Microwave-assisted synthesis and docking studies of phenylureas as candidates for the drug design against the biological warfare agent Yersinia pestis

Background: Bubonic plague is amongst the diseases with the highest potential for being used in biological warfare attacks today. Introduction: This disease, caused by the bacterium Yersina pestis, is highly infectious and can achieve 100% of fatal victims when in its most dangerous form. Besides, there is no effective vac-cine, and the chemotherapy available today against plague is ineffective if not administered at the beginning of the infection. Willing to contribute for changing this reality we propose here new phe-nylureas as candidates for the drug design against plague meant to target the enzyme dihydrofolate reductase from Y. pestis (YpDHFR). Methods: Seven phenylureas, four of them new, were synthesized, following synthetic routes adapted from procedures available in the literature, and using microwave irradiation. After, they were submitted to docking studies inside YpDHFR and human DHFR (HssDHFR) in order to check their potential as selective inhibitors. Results & Conclusion: Our results revealed four new phenylureas and a new synthetic route for this kind of molecule using microwave irradiation. Also, our docking studies pointed to two of the phe-nylureas as selective inhibitors of YpDHFR and, therefore, candidates for the design of new drugs against plague.

Synthesis of Oligonucleotides Containing the N6-(2-Deoxy-α,β-d-erythropentofuranosyl)-2,6-diamino-4-hydroxy-5-formamidopyrimidine (Fapy?dG) Oxidative Damage Product Derived from 2′-Deoxyguanosine

N6-(2-Deoxy-α,β-d-erythropentofuranosyl)-2,6-diamino-4-hydroxy-5-formamidopyrimidine (Fapy?dG) is a major DNA lesion produced from 2′-deoxyguanosine under oxidizing conditions. Fapy?dG is produced from a common intermediate that leads to 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-OxodGuo), and in greater quantities in cells. The impact of Fapy?dG on DNA structure and function is much less well understood than that of 8-OxodGuo. This is largely due to the significantly greater difficulty in synthesizing oligonucleotides containing Fapy?dG than 8-OxodGuo. We describe a synthetic approach for preparing oligonucleotides containing Fapy?dG that will facilitate intensive studies of this lesion in DNA. A variety of oligonucleotides as long as 30 nucleotides are synthesized. We anticipate that the chemistry described herein will provide an impetus for a wide range of studies involving Fapy?dG.

TRIAZOLO [4, 5-D] PYRAMIDINE DERIVATIVES AND THEIR USE AS PURINE RECEPTOR ANTAGONISTS

Compounds of formula (I) that are capable of acting as purine receptor antagonists, pharmaceutical compositions including the compounds, and methods of making the compounds, are. disclosed. The compounds and compositions can be used in treating or preventing disorders related to purine receptor hyperfunctioning.

BIOACTIVE COMPOUNDS FOR TREATMENT OF CANCER AND NEURODEGENERATIVE DISEASES

The invention provides bioactive compounds for the treatment of various malconditions such as cancer and neurodegenerative diseases including Alzheimer's disease. The chemical compounds as disclosed herein are found to show bioactivity in bioassays related to these conditions. Pharmaceutical compositions, combinations and methods of synthesis are provided, as are methods of using the compound, compositions and combinations in the treatment of the diseases.

Synthesis and antimicrobial evaluation of guanylsulfonamides

A series of guanylsulfonamides, 2-amino-9-[2-substituted-4-(4-substituted piperidin-1-sulfonyl)phenyl]-1,9-dihydropurin-6-ones, was synthesized by adopting reductive aminoformylation of 2-amino-5-nitro-6-[4-(piperidin-1-sulfonyl)phenylamino]-3H-pyrimidin- 4-one and subsequent intramolecular ring condensation as key steps. All the guanylsulfonamides were assayed for their in vitro antibacterial activities against Klebsiella pneumoniae, Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, and Streptococcus faecalis, and their antifungal activities against Aspergillus flavus, Aspergillus niger, and Candida albicans. Of the guanylsulfonamides, 13e and 13f displayed better antibacterial activities than that of Norfloxacin against the bacterial strains S. aureus and S. faecalis except 13f against S. faecalis, which exhibited the activity similar to that of Norfloxacin. Against the fungal strains A. flavus and A. niger, 13g and 13h showed similar activities to that of Griseoflavin-16 except 13h against A. niger, which displayed a profound drop in the activity compared to that of Griseoflavin-16. The remarkable inhibition of the growth of the bacterial and fungal strains makes these substances promising microbial agents.

Synthesis of oligonucleotides containing Fapy·dG (N 6-(2-deoxy-α,β-D-erythropentofuranosyl)-2, 6-diamino-4-hydroxy-5-formamidopyrimidine) using a 5′-dimethoxytrityl dinucleotide phosphoramidite

(Chemical Equation Presented). Fapy·dG (N6-(2-deoxy- α,β-D-erythropentofuranosyl)-2,6-diamino-4-hydroxy-5- formamidopyrimidine) is a modified purine lesion produced by a variety of DNA-damaging agents, which shows interesting biochemical proper