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

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

Uses

Used in Pharmaceutical Research and Development:
4-[(PYRIDIN-3-YLMETHOXYCARBONYLAMINO)-METHYL]-BENZOIC ACID is used as a building block in the synthesis of new molecules for pharmaceutical purposes, contributing to the discovery and development of innovative treatments for various diseases.
Used in Organic Synthesis:
In the field of organic synthesis, 4-[(PYRIDIN-3-YLMETHOXYCARBONYLAMINO)-METHYL]-BENZOIC ACID is employed as a key intermediate, facilitating the creation of complex organic compounds and contributing to advancements in chemical research.
Used in Medicinal Chemistry:
4-[(PYRIDIN-3-YLMETHOXYCARBONYLAMINO)-METHYL]-BENZOIC ACID is utilized as a potential therapeutic agent, exploring its efficacy in treating a range of diseases by leveraging its chemical structure to interact with biological targets.
Used in Drug Discovery:
As a component in drug discovery processes, 4-[(PYRIDIN-3-YLMETHOXYCARBONYLAMINO)-METHYL]-BENZOIC ACID is used to identify and optimize lead compounds, which may eventually progress to become new pharmaceuticals for treating specific medical conditions.

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

• 255894-58-7 1-{4-[N-(pyridin-3-ylmethoxycarbonyl)-aminomethyl]benzoyl}imidazole 
• 209783-80-2 Entinostat 
• 1026362-41-3 [4-(4-chloro-2-nitro-phenylcarbamoyl)-benzyl]-carbamic acid pyridin-3-ylmethyl ester 
• 1025886-13-8 N-(5-methyl-2-nitrophenyl)-4-benzamide 
• 1026545-09-4 [4-(4-methoxy-2-nitro-phenylcarbamoyl)-benzyl]-carbamic acid pyridin-3-ylmethyl ester 
• 1027422-59-8 [4-(5-methoxy-2-nitro-phenylcarbamoyl)-benzyl]-carbamic acid pyridin-3-ylmethyl ester 

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.

ANTICANCER AGENT DELIVERY MOLECULE

PROBLEM TO BE SOLVED: To provide a compound which can be used as an anticancer agent targeting a cancer cell that highly expresses Lysine-specific demethylase 1 (LSD1) or salt thereof. SOLUTION: The present invention provides a compound represented by the following formula (I) or a pharmaceutically acceptable salt thereof, where Ar, R1, R2, L, Z, p, q, *1 and *2 are as defined in the specifications. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

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.

SOLID FORMS OF ENTINOSTAT

Aspects of the present application relate to stable amorphous Entinostat, its amorphous solid dispersion, processes for their preparation and pharmaceutical compositions thereof. Further, aspects relate to crystalline form of Entinostat, process for its preparation and pharmaceutical compositions thereof

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.

ANTIMICROBIAL COMPOUNDS

The invention provides compounds for use in treating microbial infection in an animal. Example compounds include Pyridin-3-ylmethyl (4-((2-aminophenyl)- carbamoyl)benzyl)carbamate ("Entinostat"). The compounds can act via induction of the innate antimicrobial peptide defense system, and stimulation of autophagy.

HISTONE DEACETYLASE INHIBITORS AND USES THEREOF

The present invention discloses a group of histone deacetylase inhibitors and use thereof. The histone deacetylase inhibitors are useful in the treatment of malignant tumors and the diseases associated with differentiation and proliferation. The histone deacetylase inhibitors are the compounds represented by the following formula or salts thereof

Histone deacetylase inhibitors and uses thereof

The present invention discloses a group of histone deacetylase inhibitors and use thereof. The histone deacetylase inhibitors are useful in the treatment of malignant tumors and the diseases associated with differentiation and proliferation. The histone deacetylase inhibitors are the compounds represented by the following formula or salts thereof:

SYNTHESIS METHODS OF HISTONE DEACETYLASE INHIBITORS (HDACIS)

Simple and efficient procedures for the synthesis of histone deacetylase inhibitors. The procedure may provide MS-275 in 72% overall yields.

Improved synthesis of histone deacetylase inhibitors (HDIs) (MS-275 and CI-994) and inhibitory effects of HDIs alone or in combination with RAMBAs or retinoids on growth of human LNCaP prostate cancer cells and tumor xenografts

We have developed new, simple, and efficient procedures for the synthesis of two promising histone deacetylase inhibitors (HDIs), CI-994, (N-(2-aminophenyl)-4-acetylaminobenzamide), and MS-275 (N-(2-aminophenyl)4-[N-(pyridine-3-yl-methoxycarbonyl)aminomethyl]benzamide) from commercially available acetamidobenzoic acid and 3-(hydroxymethyl)pyridine, respectively. The procedures provide CI-994 and MS-275 in 80% and 72% overall yields, respectively. We found that the combination of four HDIs (CI-994, MS-275, SAHA, and TSA) with retinoids all-trans-retinoic acid (ATRA) or 13-cis-retinoic acid (13-CRA) or our atypical retinoic acid metabolism blocking agents (RAMBAs) 1 (VN/14-1) or 2 (VN/66-1) produced synergistic anti-neoplastic activity on human LNCaP prostate cancer cells. The combination of 2 and SAHA induced G1 and G2/M cell cycle arrest and a decrease in the S phase in LNCaP cells. 2 + SAHA treatment effectively down-regulated cyclin D1 and cdk4, and up-regulated pro-differentiation markers cytokeratins 8/18 and pro-apoptotic Bad and Bax. Following subcutaneous administration, 2, SAHA or 2 + SAHA were well tolerated and caused significant suppression/regression of tumor growth compared with control. These results demonstrate that compound 2 and its combination with SAHA are potentially useful agents that warrant further preclinical development for treatment of prostate cancer.