5822-69-5

Usage

Functional groups

two chloro groups, one phenyldiazenyl group

Potential applications

pharmaceuticals, agrochemicals
Versatile structure
Potential biological activity
Further research needed for fully understanding properties and potential uses

Upstream product

• 156-83-2 6-chloro-pyrimidine-2,4-diyldiamine 
• 2028-74-2 p-chlorobenzenediazonium chloride 
• 106-47-8 4-chloro-aniline 
• 56-06-4 2,6-diaminopyrimidin-4-ol 

Downstream Products

• 100793-47-3 6-(2-ethoxy-ethoxy)-5-(4-chloro-phenylazo)-pyrimidine-2,4-diyldiamine 
• 105339-10-4 5-(4-chloro-phenylazo)-N⁴,N⁴-dimethyl-pyrimidine-2,4,6-triyltriamine 
• 100721-75-3 5-(4-chloro-phenylazo)-N⁴,N⁴-bis-(2-hydroxy-ethyl)-pyrimidine-2,4,6-triyltriamine 
• 1194-78-1 6-chloropyrimidine-2,4,5-triamine 
• 27078-97-3 2,6-diamino-4-piperidino-5-p-chlorophenylazopyrimidine 
• 108622-61-3 2,6-diamino-4-morpholino-5-p-chlorophenylazopyrimidine 
• 247913-69-5 2,6-diamino-4-piperidino-5-p-chlorophenylazopyrimidine 
• 247913-67-3 2,6-diamino-4-diethylamino-5-p-chlorophenylazopyrimidine 
• 247913-68-4 2,6-diamino-4-dibenzylamino-5-p-chlorophenylazopyrimidine 
• 1173827-25-2 2,6-diamino-4-[(4-methoxycarbonylphenyl)methylamino]-5-(p-chlorophenyl)azopyrimidine 
• 929073-66-5 (S)-diethyl 2-{4-[2,6-diamino-5-[2-(4-chlorophenyl)-diazenyl]pyrimidin-ylamino]benzamido}pentanedioate 
• 104857-00-3 N-(4-chlorophenyl)glycine 2-<2,6-diamino-5-<(4-chlorophenyl)azo>-4-pyrimidinyl>hydrazide hemihydrate 
• 108622-61-3 5-(4-chloro-phenylazo)-6-morpholino-pyrimidine-2,4-diyldiamine 

Relevant academic research and scientific papers

Photoswitchable Intramolecular Hydrogen Bonds in 5-Phenylazopyrimidines Revealed By In Situ Irradiation NMR Spectroscopy

NMR spectroscopy with in situ irradiation uncovered unique photoswitchable intramolecular hydrogen bonds (IMHBs) in 5-phenylazopyrimidines with two hydrogen bond donors. These compounds form two stable rotamers, each with one IMHB, and the rotamer ratio changes reversibly upon UV or visible light irradiation. Strong substituent dependence of photoinduced structural changes was observed; using suitable substituents, orthogonal photoswitching can be achieved. For example, whereas UV irradiation caused switching between the two rotamers of the trans isomer of a compound with electron-donating methoxy substituent, visible light enabled to obtain the cis photoisomer. No cis isomer was detected for compounds with electro-neutral or electron-accepting substituents, but photoswitching between the two trans isomers was observed. On the other hand, compounds without hydrogen-bond donors or with one donor only formed stable cis isomers. A mechanism of the photoswitching was proposed by DFT computations.

Triazolopyrimidines identified as reversible myeloperoxidase inhibitors

Myeloperoxidase, a mammalian peroxidase involved in the immune system as an anti-microbial first responder, can produce hypochlorous acid in response to invading pathogens. Myeloperoxidase has been implicated in several chronic pathological diseases due to the chronic production of hypochlorous acid, as well as other reactive radical species. A high throughput screen and triaging protocol was developed to identify a reversible inhibitor of myeloperoxidase toward the potential treatment of chronic diseases such as atherosclerosis. The identification and characterization of a reversible myeloperoxidase inhibitor, 7-(benzyloxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine is described.

COMPOUNDS FOR IMPROVING MRNA SPLICING

Provided herein are compounds useful for improving mRNA splicing in a cell. Exemplary compounds provided herein are useful for improving mRNA splicing in genes comprising at least one exon ending in the nucleotide sequence CAA. Methods for preparing the compounds and methods of treating diseases of the central nervous system are also provided.

Synthesis and modeling study of some potential pyrimidine derivatives as HIV inhibitors

A new series of 2-amino-6-((4-aryldiazenyl)benzyloxy)-4-chloropyrimidine derivatives 4-13 and 2,6-diamino-5-arylazo-4-chloro-pyrimidine analogs 15-20 were synthesized from the pyrimidine scaffolds 3 and 14, respectively, via diazotization with various amines. Nucleophilic displacement at the 2,4-diamino-5-arylazo-6-chloro-pyrimidine 16 by different amines afforded the 4-alkylamino analogs 21-27. All new compounds were evaluated for their in vitro anti-HIV activity in MT-4 cells as non-nucleoside reverse transcriptase inhibitors on the basis of our previous work. Screening results indicated that 10 and 11 were found to be the only compounds in the series inhibiting HIV-1 replication in cell cultures with EC50 of > 1.23 and > 2.92 μgmL-1 of a CC50 of 12.30 and 17.52 μgmL -1, resulting in a selectivity index of 10 and 6, respectively. In addition, preliminary structure-activity relationships and molecular modeling of these new analogs are detailed in this manuscript.

Synthesis and biological activities of 2,4-diaminopteridine derivatives

Substituted 2,4-diaminopteridine derivatives 10a-10l were prepared in moderate to good yield. Their structures were confirmed by 1H-NMR and MS spectroscopy, as well as by elemental analysis. Their inhibitory properties against inducible nitric oxide synthase (iNOS) were evaluated in vitro. Biological tests indicated that compound 10a, 10d, 10e, 10h, 10i, and 10l showed potent inhibitory activities similar to that of methotrexate (MTX), while the activities of compound 10b, 10c, 10f, 10g, 10j, and 10k are stronger than MTX. Two compounds, i. e., 10b (IC50 = 18.85 μM) and 10i (IC 50 = 24.08 μM) were further studied for their effect on septic shock in rats and immunologically liver injured mice (in vivo). The results demonstrated that 10b and 10i had the capacity to increase the blood pressure in septic shock and showed notable protective activities on immunological hepatic injury.

N-substituted 4-aminopteridines, synthesis and use thereof as pharmaceutical agent

Compounds of formula (I), where preferably: A=a bridge of partial formula (II) or (III), R1 and R2=independently (substituted) alkyl, aryl or aralkyl, or together form a heterocycle, R3=H, —CO-Alkyl, or —CO-Aryl, R4/

Inhibition of neuronal nitric oxide synthase by 4-amino pteridine derivatives: Structure-activity relationship of antagonists of (6R)-5,6,7,8- tetrahydrobiopterin cofactor

The family of nitric oxide synthases (NOS) catalyzes the conversion of L-arginine to L-citrulline and nitric oxide (NO), an important cellular messenger molecule which has been implicated in the pathophysiology of septic shock and inflammatory and neurode

Bis (hydroxymethyl) cyclobutyl purines

Antiviral activity is exhibited by compounds having the formula STR1 and its pharmaceutically acceptable salts wherein R1 is STR2 wherein R2 is hydrogen, methyl, fluoro, chloro, bromo, iodo, hydroxy or amino; or trifluoromethyl; Rsu

Bis (hydroxymethyl) cyclobutyl triazolopyrimidines

Antiviral activity is exhibited by compounds having the formula STR1 and its pharmaceutically acceptable salts wherein R1 is STR2 R6 is hydrogen, alkyl, substituted alkyl, or aryl; and R7 and R8 are independentl