20719-43-1

Basic information

• Product Name: N⁴-(4-aminophenyl)-6-methyl-2,4-diamino-pyrimidine
• Synonyms: N⁴-(4-aminophenyl)-6-methyl-2,4-diamino-pyrimidine
• CAS NO: 20719-43-1
• Molecular Weight: 215.258
• Mol File: 20719-43-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N⁴-(4-aminophenyl)-6-methyl-2,4-diamino-pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: N⁴-(4-aminophenyl)-6-methyl-2,4-diamino-pyrimidine(20719-43-1)
• EPA Substance Registry System: N⁴-(4-aminophenyl)-6-methyl-2,4-diamino-pyrimidine(20719-43-1)

Safety Data

• Hazardous Substances Data: 20719-43-1(Hazardous Substances Data)

Upstream product

• 100-01-6 4-nitro-aniline 
• 5600-21-5 2-amino-6-methyl-4-chloropyrimidine 
• 20719-42-0 6-methyl-N⁴-(4-nitrophenyl)-2,4-diamino-pyrimidine 

Downstream Products

• 1020087-05-1 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-nitrobenzamide 
• 1020149-73-8 N-[4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl]-4-(4-quinolinylamino)benzamide 
• 1020150-22-4 4-amino-N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]benzamide 
• 1535187-96-2 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-N-4-(2-amino-6-methylpyrimidin-4-ylamino)benzamide 
• 1586047-36-0 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(pyrimidin-2-ylamino)benzamide 
• 1586047-35-9 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(pyridin-4-ylamino)benzamide 
• 1586047-49-5 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(pyridin-3-ylmethylamino)benzamide 
• 1586047-48-4 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(pyridin-4-ylmethylamino)benzamide 
• 1586047-46-2 N-[4-((2-amino-6-methylpyrimidin-4-yl)amino)phenyl]-4-(quinoline-4-carboxamide)benzamide 
• 1586047-45-1 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(2-hydroxynicotinamide)benzamide 
• 1586047-44-0 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(nicotinamide)benzamide 
• 1586047-43-9 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(isonicotinamide)benzamide 
• 1586047-42-8 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(acrindin-9-ylamino)benzamide 
• 1586047-41-7 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(7H-purin-6-ylamino)benzamide 

Relevant articles and documents

Selective non-nucleoside inhibitors of human DNA methyltransferases active in cancer including in cancer stem cells

DNA methyltransferases (DNMTs) are important enzymes involved in epigenetic control of gene expression and represent valuable targets in cancer chemotherapy. A number of nucleoside DNMT inhibitors (DNMTi) have been studied in cancer, including in cancer stem cells, and two of them (azacytidine and decitabine) have been approved for treatment of myelodysplastic syndromes. However, only a few non-nucleoside DNMTi have been identified so far, and even fewer have been validated in cancer. Through a process of hit-to-lead optimization, we report here the discovery of compound 5 as a potent non-nucleoside DNMTi that is also selective toward other AdoMet-dependent protein methyltransferases. Compound 5 was potent at single-digit micromolar concentrations against a panel of cancer cells and was less toxic in peripheral blood mononuclear cells than two other compounds tested. In mouse medulloblastoma stem cells, 5 inhibited cell growth, whereas related compound 2 showed high cell differentiation. To the best of our knowledge, 2 and 5 are the first non-nucleoside DNMTi tested in a cancer stem cell line.

Synthetic approaches to DNMT inhibitor SGI-1027 and effects on the U937 leukemia cell line

The known DNMT inhibitor SGI-1027 4 has been synthesized using as key steps Pd-catalyzed Ar-N bond formation reactions performed in a sequential or convergent manner. In the former approach, a by-product, which corresponds to the incorporation of two units of 4-chloroquinoline, was also isolated. The biological effects of compound 4 in the U937 human leukemia cell line are also described.

QUINOLINE DERIVATIVES FOR MODULATING DNA METHYLATION

Quinoline derivatives, particularly 4-anilinoquinoline derivatives, are provided. Such quinoline derivatives can be used for modulation of DNA methylation, such as effective inhibition of methylation of cytosine at the C-5 position, for example via selective inhibition of DNA methyltransferase DNMT1. Methods for synthesizing numerous 4-anilinoquinoline derivatives and for modulating DNA methylation are provided. Also provided are methods for formulating and administering these compounds or compositions to treat conditions such as cancer and hematological disorders.