18620-73-0

Basic information

• Product Name: 2,4-DIAMINO-5-NITROPYRIMIDINE
• Synonyms: 2,4-DIAMINO-5-NITROPYRIMIDINE;5-NITROPYRIMIDINE-2,4-DIAMINE;5-Nitro-2,4-pyriMidinediaMine;NSC 122004
• CAS NO: 18620-73-0
• Molecular Formula: C₄H₅N₅O₂
• Molecular Weight: 155.11
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides
• Mol File: 18620-73-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 345-350°C
• Boiling Point: 509°Cat760mmHg
• Flash Point: 261.6°C
• Appearance: /
• Density: 1.68g/cm³
• Vapor Pressure: 1.77E-10mmHg at 25°C
• Refractive Index: 1.746
• Storage Temp.: -20?C Freezer
• Solubility: DMSO, Hot Methanol, Hot 2N Hydrochloric Acid
• CAS DataBase Reference: 2,4-DIAMINO-5-NITROPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIAMINO-5-NITROPYRIMIDINE(18620-73-0)
• EPA Substance Registry System: 2,4-DIAMINO-5-NITROPYRIMIDINE(18620-73-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 18620-73-0(Hazardous Substances Data)

Usage

Description

2,4-DIAMINO-5-NITROPYRIMIDINE is an organic compound characterized by its fine yellow powder appearance. It is known for its strong preferential binding to the enzyme dihydrofolate reductase, competing with the substrate Dihydrofolic Acid.

Uses

Used in Pharmaceutical Industry:
2,4-DIAMINO-5-NITROPYRIMIDINE is used as a pharmaceutical compound for its ability to bind with dihydrofolate reductase, an enzyme involved in the synthesis of DNA and RNA. This interaction makes it a potential candidate for the development of drugs targeting various diseases, particularly those related to the inhibition of this enzyme.
Used in Enzyme Inhibition Studies:
In the field of biochemistry and molecular biology, 2,4-DIAMINO-5-NITROPYRIMIDINE is utilized as a research tool for studying the function and inhibition of dihydrofolate reductase. Its strong binding properties allow scientists to investigate the enzyme's role in cellular processes and the potential therapeutic applications of inhibiting its activity.
Used in Drug Development:
2,4-DIAMINO-5-NITROPYRIMIDINE is employed as a key component in the development of new drugs, particularly those aimed at treating conditions where dihydrofolate reductase plays a significant role. Its chemical properties and binding affinity make it a valuable starting point for designing and synthesizing novel therapeutic agents.

InChI:InChI=1/C4H5N5O2/c5-3-2(9(10)11)1-7-4(6)8-3/h1H,(H4,5,6,7,8)

Upstream product

• 7664-41-7 ammonia 
• 49845-33-2 2,4-Dichloro-5-nitropyrimidine 
• 98027-74-8 2-chloro-5-nitro-4-thiocyanatopyrimidine 
• 160948-35-6 2-amino-4-chloro-5-nitropyrimidine 
• 84097-27-8 4-amino-2-guanidino-5-nitropyrimidine hydrochloride 
• 1920-66-7 4-amino-2-chloro-5-nitropyrimidine 

Downstream Products

• 1086214-44-9 C₁₈H₁₃N₅O₄ 
• 3546-50-7 pyrimidine-2,4,5-triamine 

Relevant articles and documents

Folate-Synthesizing Enzyme System as Target for Development of Inhibitors and Inhibitor Combinations against Candida albicans - Synthesis and Biological Activity of New 2,4-Diaminopyrimidines and 4′-Substituted 4-Aminodiphenyl Sulfones

The paper describes the design, synthesis, and testing of inhibitors of folate-synthesizing enzymes and of whole cell cultures of Candida albicans. The target enzymes used were dihydropteroic acid synthase (SYN) and dihydrofolate reductase (DHFR). Several series of new 2,4-diaminopyrimidines were synthesized and tested as inhibitors of DHFR and compared with their activity against DHFR derived from mycobacteria and Escherichia coli. To test for selectivity, also rat DHFR was used. A series of substituted 4-aminodiphenyl sulfones was tested for inhibitory activity against SYN and the I50 values compared to those obtained previously against Plasmodium berghei- and E. coll-derived SYN. Surprisingly, QSAR equations show very similar structural dependencies. To find an explanation for the large difference in the I50 values observed for enzyme inhibition (SYN, DHFR) and for inhibition of cell cultures of Candida, mutant strains with overexpressed efflux pumps and strains in which such pumps are deleted were included in the study and the MICs compared. Efflux pumps were responsible for the low activity of some of the tested derivatives, others showed no increase in activity after pumps were knocked out. In this case it may be speculated that these derivatives are not able to enter the cells.

Synthesis of Some Substituted Guanidinopyrimidines and their Structural Assignment by 13C and 1H NMR

A series of substituted 2- and 4-guanidinopyrimidines were prepared by reaction of halopyrimidines with guanidine; alkylamino and amino substituents were introduced by subsequent halogen replacement by primary amines or ammonia or the catalytic reduction of nitro groups.Structural assignments were made on the basis of 13C and 1H nmr.A guanidinopteridine and a bispyrimidinylguanidine were also synthesized.Some unsuccessful reaction illustrated the low nucleophilic reactivity and thermal instability of the guanidine group.