179343-43-2

Basic information

• Product Name: 3-Pyridinecarboxaldehyde,4,6-diamino-(9CI)
• Synonyms: 3-Pyridinecarboxaldehyde,4,6-diamino-(9CI);4,6-Diamino-3-pyridinecarboxaldehyde
• CAS NO: 179343-43-2
• Molecular Formula: C₆H₇N₃O
• Molecular Weight: 137.13928
• Product Categories: PYRIDINE
• Mol File: 179343-43-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Pyridinecarboxaldehyde,4,6-diamino-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarboxaldehyde,4,6-diamino-(9CI)(179343-43-2)
• EPA Substance Registry System: 3-Pyridinecarboxaldehyde,4,6-diamino-(9CI)(179343-43-2)

Safety Data

• Hazardous Substances Data: 179343-43-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
3-Pyridinecarboxaldehyde,4,6-diamino-(9CI) is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and reactivity contribute to the development of new compounds with potential therapeutic and pesticidal properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3-Pyridinecarboxaldehyde,4,6-diamino-(9CI) is utilized as a building block for the preparation of complex organic molecules. Its presence in the synthesis process can lead to the creation of novel compounds with improved pharmacological properties.
Used in Organic Synthesis:
3-Pyridinecarboxaldehyde,4,6-diamino-(9CI) also serves as a reagent in chemical reactions, playing a crucial role in organic synthesis. Its ability to participate in various chemical transformations allows for the production of a diverse array of organic compounds for different applications.

Upstream product

• 75776-47-5 2,4-diamino-5-cyanopyridine 

Downstream Products

• 78433-88-2 2-(2,6-dichlorophenyl)acetamide 
• 293301-35-6 3-(3,5-Dimethoxyphenyl)-7-{[3-(4-methylpiperazin-1-yl)propyl]amino}-1,6-naphthyridin-2-amine 
• 293301-24-3 3-(3,5-Dimethoxyphenyl)-7-fluoro-1,6-naphthyridin-2-amine 
• 293301-29-8 2,7-Difluoro-3-(3,5-dimethoxyphenyl)-1,6-naphthyridine 
• 179342-45-1 3-(2,6-Dichlorophenyl)-1,6-naphthyridine-2,7-diamine 
• 293301-09-4 3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamine 

Relevant articles and documents

Synthesis and structure-activity relationships of 7-substituted 3-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-ones as selective inhibitors of pp60(c-src)

7-Substituted 3-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-ones are potent inhibitors of protein tyrosine kinases, with some selectivity for c-Src. The compounds were prepared by condensing 4,6-diaminonicotinaldehyde with 2,6-dichlorophenylacetonitrile and selectively converting the 2- and 7-amino groups of the product to hydroxy and fluoro groups, respectively, by prolonged diazotization in 50% aqueous fluoboric acid. N-Methylation, followed by treatment with aliphatic diamines, aromatic amines, or their derived lithium anions, gave the desired compounds. Selected isomeric 1,8-naphthyridin-2(1H)-ones were also prepared in order to evaluate the relative contributions of both ring A aza atoms of the related pyrido[2,3-d]pyrimidin-7(8H)-ones to the inhibitory activity. The compounds were evaluated for their ability to prevent phosphorylation of a model substrate by c-Src, FGF-1 receptor, and PDGF-β receptor enzymes. Overall, there was a high degree of correlation of the activities against the different kinases, with c-Src being generally the most sensitive to structural changes. 1,6-Naphthyridin-2(1H)-one analogues bearing basic aliphatic side chains [7-NH(CH2)(n)NRR, 7-NHPhO(CH2)(n)NRR, or 7-NHPhN(CH2)4NMe] were the most potent against c-Src (IC50s of 10-80 nM), showing good selectivity with respect to PDGFR (10-300-fold) but less with respect to FGFR. The 1,6-naphthyridin-2(1H)-ones showed broadly similar activity to the analogous pyrido[2,3-d]-pyrimidin-7(8H)-ones, whereas the 1,8-naphthyridin-2(1H)-ones were at least 103-fold less potent. These results, indicating that the 3-aza atom in the pyrido[2,3-d]pyrimidin-7(8H)-ones is mandatory, whereas the 1-aza atom is not, support the published binding model for these compounds to c-Src (J. Med. Chem. 1998, 41, 1752), where the 3-aza and 2-NH atoms form a bidentate H-bond donor - acceptor motif that interacts with Met341 and the 1-aza atom is not involved in specific binding interactions.

Naphthyridinones for inhibiting protein tyrosine kinase and cell cycle kinase mediated cellular proliferation

PCT No. PCT/US98/16848 Sec. 371 Date Jan. 26, 2000 Sec. 102(e) Date Jan. 26, 2000 PCT Filed Aug. 13, 1998 PCT Pub. No. WO99/09030 PCT Pub. Date Feb. 25, 1999This invention relates to the inhibition of protein tyrosine kinase (PTK) and cell cycle kinase mediated cellular proliferation. More specifically, this invention relates to naphthyridinones and their use in inhibiting cellular proliferation and PTK or cell cycle kinase enzymatic activity.