10166-39-9

Basic information

• Product Name: N-(2-CHLOROPHENYL)ANTHRANILIC ACID
• Synonyms: N-(2-CHLOROPHENYL)ANTHRANILIC ACID
• CAS NO: 10166-39-9
• Molecular Formula: C₁₃H₁₀ClNO₂
• Molecular Weight: 247.68
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 10166-39-9.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(2-CHLOROPHENYL)ANTHRANILIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-CHLOROPHENYL)ANTHRANILIC ACID(10166-39-9)
• EPA Substance Registry System: N-(2-CHLOROPHENYL)ANTHRANILIC ACID(10166-39-9)

Safety Data

• Hazardous Substances Data: 10166-39-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 2077, 1989 DOI: 10.1080/00397918908052600

Upstream product

• 95-51-2 o-chloroaniline 
• 445-29-4 o-fluoro-benzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 123-51-3 i-Amyl alcohol 
• 16463-38-0 potassium 2-chlorobenzoate 
• 17264-73-2 sodium o-bromobenzoate 
• 88-65-3 2-bromobenzoic-acid 
• 118-91-2 ortho-chlorobenzoic acid 
• 16497-87-3 potassium o-bromobenzoate 

Downstream Products

• 78938-56-4 2-(2-Chloro-phenylamino)-benzoic acid 2-[(E)-2,4-dioxo-imidazolidin-1-ylimino]-ethyl ester 
• 18201-67-7 2-(2-chloroanilino)benzamide 
• 18201-84-8 2-[(2-chlorophenyl)amino]benzonitrile 
• 23310-34-1 (E)-1,1'-bis-(2-chloro-phenyl)-1H,1'H-[3,3']bi[benzo[c]isothiazolylidene] 
• 16095-38-8 1-(2-chloro-phenyl)-1,2-dihydro-benzo[d][1,3]oxazin-4-one 
• 1205-40-9 N-phenyl-2-chloroaniline 
• 10166-44-6 4,9-dichloroacridine 
• 860530-18-3 N-(2-chloro-phenyl)-anthranilic acid-anhydride 

Relevant articles and documents

Binding of N-phenylanthranilic acid derivatives to bovine serum albumin

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Design, synthesis, biological evaluation, and docking study of acetylcholinesterase inhibitors: New acridone-1,2,4-oxadiazole-1,2,3-triazole hybrids

In this study, novel acridone-1,2,4-oxadiazole-1,2,3-triazole hybrids were designed, synthesized, and evaluated for their acetylcholinesterase and butyrylcholinesterase inhibitory activity. Among various synthesized compounds, 10-((1-((3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)acridin-9(10H)-one 10b showed the most potent anti-acetylcholinesterase activity (IC50 = 11.55 μm) being as potent as rivastigmine. Also docking outcomes were in good agreement with in vitro results confirming the dual binding inhibitory activity of compound 10b. A novel series of acridone-1,2,4-oxadiazole-1,2,3-triazole hybrids were synthesized and evaluated in vitro for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities.

Design, synthesis and biological evaluation of N-anthraniloyl tryptamine derivatives as pleiotropic molecules for the therapy of malignant glioma

COX-2 and STAT3 are two key culprits in the glioma microenvironment. Herein, to inhibit COX-2 and block STAT3 signaling, we disclosed 27 N-anthraniloyl tryptamine compounds based on the combination of melatonin derivatives and N-substituted anthranilic acid derivatives. Among them, NP16 showed the best antiproliferative activity and moderate COX-2 inhibition. Of note, NP16 decreased the level of p-JAK2 and p-STAT3, and blocked the nuclear translocation of STAT3 in GBM cell lines. Moreover, NP16 downregulated the MMP-9 expression of BV2 cells in a co-culture system of BV2 and C6 glioma cells, abrogated the proliferative/invasive/migratory abilities of GBM cells, induced apoptosis by ROS and the Bcl-2-regulated apoptotic pathway, and induced obvious G2/M arrest in glioma cells in vitro. Furthermore, NP16 displayed favorable pharmacokinetic profiles covering long half-life (11.43 ± 0.43 h) and high blood-brain barrier permeability. Finally, NP16 effectively inhibited tumor growth, promoted the survival rate, increased the expression of E-cadherin and reduced overproduction of PGE2, MMP-9, VEGF-A and the level of p-STAT3 in tumor tissue, and improved the anxiety-like behavior in C6 glioma model. All these evidences demonstrated N-anthraniloyl tryptamine derivatives as multifunctional anti-glioma agents with high potency could drain the swamp to beat glioma.