19407-42-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Acetamido-6-chlorobenzoic acid is used as a pharmaceutical intermediate for its potential role in the development of new drugs. Its anti-inflammatory properties make it a candidate for treating conditions that involve inflammation.
Used in Research and Laboratory Settings:
In the realm of scientific research, 2-Acetamido-6-chlorobenzoic acid serves as a crucial intermediate in the synthesis of a variety of organic compounds, facilitating the advancement of chemical research and the creation of novel chemical entities.

InChI:InChI=1/C9H8ClNO3/c1-5(12)11-7-4-2-3-6(10)8(7)9(13)14/h2-4H,1H3,(H,11,12)(H,13,14)

Upstream product

• 7463-35-6 N-(3-chloro-2-methylphenyl)acetamide 
• 108-24-7 acetic anhydride 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 7487-88-9 magnesium sulfate 
• 6259-40-1 3-chloro-2-methyl-aniline; hydrochloride 
• 10101-50-5 sodium permanganate 
• 2148-56-3 2-chloro-6-aminobenzoic acid 

Downstream Products

• 35118-96-8 2-acetylamino-6-anilino-benzoic acid 
• 812644-77-2 2-acetylamino-6-(3-nitro-anilino)-benzoic acid 
• 2148-56-3 2-chloro-6-aminobenzoic acid 
• 70625-65-9 methyl 2-acetamido-6-chlorobenzoate 
• 41632-04-6 methyl 6-chloroanthranilate 
• 66073-40-3 1-aminoacridin-9(10H)-one 
• 578-06-3 acridin-1-ylamine 
• 50-30-6 2,6-dichlorobenzoic acid 
• 76754-72-8 N-(3-nitro-phenyl)-m-phenylenediamine 
• 21147-93-3 1,6-Dichlor-fluorenon 
• 100960-33-6 2-amino-6-chlorobenzoic acid hydrochloride 
• 60233-66-1 5-chloroquinazolin-4-ol 
• 400784-50-1 4-hydroxy-5-chloro-8-nitro-quinazoline 

Relevant academic research and scientific papers

Synthesis and antitumor evaluation of novel 5-substituted-4-hydroxy-8- nitroquinazolines as EGFR signaling-targeted inhibitors

The synthesis and biological activity of a series of novel 5-substituted-4-hydroxy-8-nitroquinazolines that may function as inhibitors of EGFR- and/or ErbB-2-related oncogenic signaling are described. These compounds were prepared by SNAr reaction of 5-chloro-4-hydroxy-8- nitroquinazoline with alkyl or aryl amines, or alkyl alcohol as nucleophiles. Although the enzyme assay showed a weak inhibition effect against both EGFR and ErbB-2 tyrosine kinases, the cell-based antitumor activity turned out promising. Compounds having 5-anilino substituent exhibit high potency with 5-(4-methoxy)anilino-4-hydroxy-8-nitroquinazoline (1h) being the best dual EGFR/ErbB-2 inhibitors, which effectively inhibited the growth of both EGFR (MDA-MB-468, IC50 50 = 13 μM) overexpressing human tumor cell lines in vitro. More interestingly, the variation of the substituent(s) at the 3- and/or 4-position of the 5-anilino portion was found to modulate the selectivity and potency dramatically. However, compounds having an alkylamino or alkyloxy group at the 5-position of 4-hydroxy-8-nitroquinazolines are essentially inactive. These results are consistent with molecular modeling observations. This study was the first attempt to identify new structural types of dual EGFR/ErbB-2-related signaling inhibitors by incorporation of the anilino group at the 5-position of 4-hydroxy-8-nitroquinazolines' core structure, providing promising new templates for further development of potent inhibitors targeting both EGFR and ErbB-2 tyrosine kinases.

Ligand-Enabled γ-C(sp3)?H Olefination of Free Carboxylic Acids

We report the ligand-enabled C?H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.

Herbicidal substituted benzoylsulfonamides

Compound of the formula STR1 in which A is O, S, or NR3 ; G is CH or N; R and R1 are independently alkyl, alkoxy, haloalkoxy or alkylamino; R2 is phenyl, substituted phenyl, alkyl, cycloalkyl, haloalkyl or --CH2 [(R4)C(R5)n --Z; R3 and R7 are, independently, hydrogen, alkyl, --C(O)NH2 or --C(O)alkyl; R4 and R5 are independently hydrogen, alkyl, or halogen; R6 is halogen, alkyl, alkoxy, haloalkoxy, NO2, amino, alkyl substituted amino, or acyl substituted amino; n is 0 to 5; Z is cyano, amino, alkylamino, dialkylamino, --NHCO2 alkyl, alkoxy, alkylthio, alkylsulfonyl, alkenyl, alkynyl, phenyl or substituted phenyl; and Q is hydrogen, halogen, alkyl, alkoxy, haloalkoxy, nitro, amino, haloalkyl, alkythio, alkylsulfonyl, phenyl, substituted phenyl or phenoxy; or a 5 or 6 membered aromatic heterocycle having the formula STR2 in which "m" is 0 or 1; A' is O, S, or NR7 ; and X, X', Y, Y', W, W', V, V', U and Z' are independently N, O, S, --CH-- or --CR6. Intermediates for preparation of the benzoylsulfonamides are also disclosed.

Linear and Proximal Benzo-Separated Alkylated Xanthines as Adenosine-Receptor Antagonists

The linear and proximal benzo-separated derivatives of 8-phenyltheophylline, 1,3-diethyl-8-phenylxanthine, 1,3-dipropylxanthine, 1,3-dibutylxanthine, 3-isobutyl-1-methylxanthine, theophylline, caffeine, and isocaffeine have been synthesized and evaluated for affinity at the A1 and A2 adenosine receptors.Although structure-activity relationships in the benzo-separated series differed from the relationships in simple xanthines, the most potent of the benzo-separated xanthines were about equal in affinity to the most potent of the corresponding xanthines.On the basis of the present results and the diverse structures reported in the literature as non-xanthine adenosine antagonists, it appears that the primary requirement for the adenosine-receptor affinity in nonnucelosides is a flat, neutral, fused-ring heterocycle and that once this requirement is met there are numerous potential binding modes.