241809-79-0

Basic information

• Product Name: 4-[(PYRIDIN-3-YLMETHOXYCARBONYLAMINO)-METHYL]-BENZOIC ACID
• Synonyms: 4-[(PYRIDIN-3-YLMETHOXYCARBONYLAMINO)-METHYL]-BENZOIC ACID;4-({[(3-Pyridinylmethoxy)Carbonyl]Amino}Methyl)Benzoic Acid;4-(((pyridin-3-ylmethoxy)carbonyl)methyl)benzoic acid;Benzoicacid,4-[[[(3-pyridinylmethoxy)carbonyl]amino]methyl]-
• CAS NO: 241809-79-0
• Molecular Formula: C₁₅H₁₄N₂O₄
• Molecular Weight: 286.28
• Mol File: 241809-79-0.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 548.3°Cat760mmHg
• Flash Point: 285.4°C
• Appearance: /
• Density: 1.316g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.23±0.10(Predicted)
• CAS DataBase Reference: 4-[(PYRIDIN-3-YLMETHOXYCARBONYLAMINO)-METHYL]-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(PYRIDIN-3-YLMETHOXYCARBONYLAMINO)-METHYL]-BENZOIC ACID(241809-79-0)
• EPA Substance Registry System: 4-[(PYRIDIN-3-YLMETHOXYCARBONYLAMINO)-METHYL]-BENZOIC ACID(241809-79-0)

Safety Data

• Hazardous Substances Data: 241809-79-0(Hazardous Substances Data)

Usage

General Description

4-[(Pyridin-3-ylmethoxycarbonylamino)methyl]-benzoic acid is a chemical compound comprising a benzoic acid molecule attached to a pyridine ring with a methoxycarbonylamino group. 4-[(PYRIDIN-3-YLMETHOXYCARBONYLAMINO)-METHYL]-BENZOIC ACID is commonly used as a building block in organic synthesis and pharmaceutical research. It acts as a potential therapeutic agent for various diseases and is also used in the synthesis of new molecules for pharmaceutical purposes. It is known for its potential medicinal properties and can be used in the development of new drugs and treatments.

InChI:InChI=1/C15H14N2O4/c18-14(19)13-5-3-11(4-6-13)9-17-15(20)21-10-12-2-1-7-16-8-12/h1-8H,9-10H2,(H,17,20)(H,18,19)

Upstream product

• 56-91-7 p-aminomethylbenzoic acid 
• 212632-27-4 pyridin-3-ylmethyl 1H-imidazole-1-carboxylate 
• 100-55-0 3-hydroxymethylpyridin 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 1013330-59-0 C₃₀H₃₀N₄O₅S 
• 1013330-57-8 1,1-dimethylethyl {3-[({4-[({[(pyridin-3-ylmethyl)oxy]carbonyl}amino)methyl]phenyl}carbonyl)amino]biphenyl-4-yl}carbamate 
• 936755-47-4 pyridin-3-ylmethyl {4-[({4-[(tert-butoxycarbonyl)amino]-1-phenyl-1H-pyrazol-3-yl}amino)carbonyl]benzyl}carbamate 
• 1201690-73-4 C₂₂H₂₀N₄O₅ 
• 1201689-77-1 N-(2-aminobenzyl)-4-[(3-pyridylmethoxycarbonyl)aminomethyl]benzamide 
• 1201689-78-2 N-(2-pyridyl)-4-[(3-pyridylmethoxycarbonyl)aminomethyl]benzamide 
• 209783-80-2 Entinostat 

Relevant articles and documents

Synthesis of n-substituted benzamide derivatives and their evaluation as antitumor agents

Background: Histone deacetylases inhibitors (HDACIs) with different chemical structures have been reported to play an important role in the treatment of cancer. Objective: The study aims to modify the structure of Entinostat (MS-275) to discover new compounds with improved anti-proliferative activities and perform SAR studies on this class of bioactive compounds. Methods: Fourteen N-substituted benzamide derivatives were synthesized and their antiproliferative activities were tested with four cancer cell lines (MCF-7, A549, K562 and MDA-MB231) by MTT assay. Results: Compared with MS-275, six compounds exhibited comparable or even better antiproliferative activities against specific/certain cancer cell lines. Conclusion: The preliminary SARs showed that (i) the 2-substituent of the phenyl ring in the R group and heteroatoms of amide which can chelate with zinc ion are critical to the antiproliferative activity and (ii) chlorine atom or nitro-group on the same benzene ring largely decreases their anti-proliferative activity. Molecular docking study illustrated the interaction (binding affinity) between the synthesized compounds and HDAC2 was observed to be similar to that of MS-275.

CRYSTALLINE FORMS OF ENTINOSTAT

Entinostat is a histone deacetylase inhibitor undergoing clinical investigation in multiple types of solid tumors, such as breast cancer, and hematologic cancers. Crystalline form D and E of Entinostat and crystal form A in high crystal purity are provided. Crystalline form D can be obtained in high chemical purity, exhibits improved water solubility and allows efficient purification of Entinostat with removal of coloured impurities. Processes for the preparation of such crystalline forms and of form A with improved chemical and crystal purity are also provided.

Novel ultrasonic synthesis method for Entinostat

The invention relates to a novel ultrasonic synthesis method for Entinostat. The method comprises the following steps: (1) 4-[N-(pyridine-3-methoxycarbonyl)aminomethyl]benzoic acid is prepared under an ultrasonic condition; (2) the compound is subjected to condensation with o-phenylenediamine under an ultrasonic condition in presence of a condensing agent and a catalyst, and a crude Entinostat product is obtained; (3) the crude Entinostat product is subjected to backflow beating in ethyl alcohol, and the final Entinostat product is prepared. The method has the advantages that the production cycle is short, the process is simple, the yield is high, and the product purity is high.