78433-88-2

Usage

Uses

Used in Chemical Synthesis:
2,6-Dichlorophenylacetamide is used as an intermediate in the synthesis of various organic compounds. Its unique structure, containing chlorine atoms and phenyl rings, makes it a valuable building block for creating a range of chemical products.
Used in Pharmaceutical Industry:
2,6-Dichlorophenylacetamide is used as a starting material for the development of new pharmaceutical compounds. Its molecular structure can be modified to create potential drug candidates with specific therapeutic properties.
Used in Pesticide Formulation:
2,6-Dichlorophenylacetamide is used as an active ingredient in the formulation of certain pesticides. Its chemical properties allow it to be effective against pests, making it a component in agricultural chemical products.
Used in Research and Development:
2,6-Dichlorophenylacetamide is used as a research compound in academic and industrial laboratories. Its unique characteristics make it an interesting subject for studies in organic chemistry, material science, and related fields.

InChI:InChI=1/C8H7Cl2NO/c9-6-2-1-3-7(10)5(6)4-8(11)12/h1-3H,4H2,(H2,11,12)

Upstream product

• 110-80-5 2-ethoxy-ethanol 
• 3215-64-3 2,6-dichlorophenylacetonitrile 
• 179343-43-2 4,6-Diaminonicotinaldehyde 

Relevant academic research and scientific papers

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.

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.