91-38-3

Basic information

• Product Name: 4-CHLORO-2-(4-METHOXY-PHENYLAMINO)-BENZOIC ACID
• Synonyms: 4-CHLORO-2-(4-METHOXY-PHENYLAMINO)-BENZOIC ACID;4-CHLORO-N-(4-METHOXYPHENYL)ANTHRANILIC ACID;4-chloro-2-(4-methoxyphenyl)anthranilic acid;4-CHLORO-2-(4-METHOXYANILINO)BENZOIC ACID;2-(4-Methoxyanilino)-4-chlorobenzoic acid
• CAS NO: 91-38-3
• Molecular Formula: C₁₄H₁₂ClNO₃
• Molecular Weight: 278.71092
• EINECS: 202-065-2
• Product Categories: pharmacetical
• Mol File: 91-38-3.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 433.6°C at 760 mmHg
• Flash Point: 216°C
• Appearance: /
• Density: 1.2527 (rough estimate)
• Vapor Pressure: 2.76E-08mmHg at 25°C
• Refractive Index: 1.6470 (estimate)
• CAS DataBase Reference: 4-CHLORO-2-(4-METHOXY-PHENYLAMINO)-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-(4-METHOXY-PHENYLAMINO)-BENZOIC ACID(91-38-3)
• EPA Substance Registry System: 4-CHLORO-2-(4-METHOXY-PHENYLAMINO)-BENZOIC ACID(91-38-3)

Safety Data

• Hazardous Substances Data: 91-38-3(Hazardous Substances Data)

Usage

General Description

4-CHLORO-2-(4-METHOXY-PHENYLAMINO)-BENZOIC ACID is a chemical compound with the molecular formula C14H11ClN2O3. It is a derivative of benzoic acid and contains a chlorine atom and a 4-methoxy-phenylamino group. 4-CHLORO-2-(4-METHOXY-PHENYLAMINO)-BENZOIC ACID is often used as an intermediate in the synthesis of pharmaceuticals and organic compounds. It has been studied for its potential anti-inflammatory and antioxidant properties and is used in research and development of new drugs. 4-CHLORO-2-(4-METHOXY-PHENYLAMINO)-BENZOIC ACID may also have applications in the field of organic chemistry and materials science due to its unique molecular structure.

InChI:InChI=1/C14H12ClNO3/c1-19-11-5-3-10(4-6-11)16-13-8-9(15)2-7-12(13)14(17)18/h2-8,16H,1H3,(H,17,18)

Upstream product

• 50-84-0 2,4 dichlorobenzoic acid 
• 104-94-9 4-methoxy-aniline 
• 74-11-3 para-chlorobenzoic acid 
• 212892-02-9 methyl 4-chloro-2-(((trifluoromethyl)sulfonyl)oxy)benzoate 
• 32082-99-8 methyl 4-chloro-2-(4-methoxyphenyl)aminobenzoate 

Downstream Products

• 857602-05-2 4-chloro-2-[(4-methoxy-2-nitrophenyl)amino]benzoic acid 

Relevant articles and documents

Design, synthesis and biological evaluation of novel phthalazinone acridine derivatives as dual PARP and Topo inhibitors for potential anticancer agents

In this study, we designed and synthesized a series of phthalazinone acridine derivatives as dual PARP and Topo inhibitors. MTT assays indicated that most of the compounds significantly inhibited multiple cancer cells proliferation. In addition, all the compounds displayed Topo II inhibition activity at 10 mol/L, and also possessed good PARP-1 inhibitory activities. Subsequent mechanistic studies showed that compound 9a induced remarkable apoptosis and caused prominent S cell cycle arrest in HCT116 cells. Our study suggested that 9a inhibiting Topo and PARP concurrently can be a potential lead compound for cancer therapy.

Design, synthesis and biological research of novel N-phenylbenzamide-4-methylamine acridine derivatives as potential topoisomerase I/II and apoptosis-inducing agents

A series of novel N-phenylbenzamide-4-methylamine acridine derivatives were designed and synthesized based initially on the structure of amsacrine (m-AMSA). Molecular docking suggested that the representative compound 9a had affinity for binding DNA topoisomerase (Topo) II, which was comparable with that of m-AMSA, and furthermore that 9a could have preferential interactions with Topo I. After synthesis of 9a and analogues 9b-9f, these were all tested in vitro and the synthesized compounds displayed potent antiproliferative activity against three different cancer cell lines (K562, CCRF-CEM and U937). Among them, compounds 9b, 9c and 9d exhibiting the highest activity with IC50 value ranging from 0.82 to 0.91 μM against CCRF-CEM cells. In addition, 9b and 9d also showed high antiproliferative activity against U937 cells, with IC50 values of 0.33 and 0.23 μM, respectively. The pharmacological mechanistic studies of these compounds were evaluated by Topo I/II inhibition, western blot assay and cell apoptosis detection. In summary, 9b effectively inhibited the activity of Topo I/II and induced DNA damage in CCRF-CEM cells and, moreover, significantly induced cell apoptosis in a concentration-dependent manner. These observations provide new information and guidance for the structural optimization of more novel acridine derivatives.

Design and synthesis of novel quinacrine-[1,3]-thiazinan-4-one hybrids for their anti-breast cancer activity

In an attempt to develop effective and safe anticancer agents, we designed, synthesized and examined 23 novel quinacrine (QC) derivatives by combining the 9-aminoacridine scaffold and the [1,3]thiazinan-4-ones group. Most of these hybrids showed strong anticancer activities, among which 3-(3-(6-chloro-2-methoxyacridin-9-ylamino)propyl)-2-(thiophen-2-yl)-1,3-thiazinan-4-one (25; VR151) effectively killed many different cancer cell types, including eight breast cancer cell lines with different genetic background, two prostate cancer and two lung cancer cell lines. In contrast, compound 25 is less effective against non-cancer cells, suggesting it may be less toxic to humans. Our data showed that cancer cells are arrested in S phase for a prolonged period due to the down-regulation of DNA replication, leading to eventual cell death. We have also shown that the S phase arrest may be resulted by the down-regulation of cyclin A coupled with the continued up-regulation of cyclin E, which coincide with the down-regulation of mTor-S6K and mTor-4EBP1 pathways.