81918-01-6

Basic information

• Product Name: Diethyl 2-[4-(chlorobenzoyl)amino]Malonate
• Synonyms: Diethyl 2-[4-(chlorobenzoyl)amino]Malonate;DIETHYL 4-CHLOROBENZAMIDOMALONATE[REBAMIPIDE INTERMEDIATE];[(4-Chlorobenzoyl)-amino]-propanedioic acid diethyl ester;Diethyl 2-(4-chlorobenzaMido)Malonate;diethyl [(4-chlorobenzoyl)amino]propanedioate;diethyl 2-[(4-chlorobenzoyl)amino]propanedioate
• CAS NO: 81918-01-6
• Molecular Formula: C₁₄H₁₆ClNO₅
• Molecular Weight: 313.73354
• Product Categories: (intermediate of rebamipide)
• Mol File: 81918-01-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 458.625°C at 760 mmHg
• Flash Point: 231.168°C
• Appearance: /
• Density: 1.264g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: 2-8°C
• PKA: 11.56±0.46(Predicted)
• CAS DataBase Reference: Diethyl 2-[4-(chlorobenzoyl)amino]Malonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl 2-[4-(chlorobenzoyl)amino]Malonate(81918-01-6)
• EPA Substance Registry System: Diethyl 2-[4-(chlorobenzoyl)amino]Malonate(81918-01-6)

Safety Data

• Hazardous Substances Data: 81918-01-6(Hazardous Substances Data)

Usage

Uses

Diethyl 2-(4-chlorobenzamido)malonate is a reagent used in the synthesis of indole-based PPARγ ligands

InChI:InChI=1/C14H16ClNO5/c1-3-20-13(18)11(14(19)21-4-2)16-12(17)9-5-7-10(15)8-6-9/h5-8,11H,3-4H2,1-2H3,(H,16,17)

Upstream product

• 6829-40-9 aminomalonic acid diethyl ester 
• 122-01-0 4-chloro-benzoyl chloride 
• 13433-00-6 diethyl aminomalonate hydrochloride 

Downstream Products

• 1028268-32-7 ethyl 2-(4-chlorobenzamido)-2-ethoxyoxo-3-[2-(1H)-quinolin-4-yl]propionate 
• 1379481-87-4 (E)-2-(p-chlorophenyl)-4,4-bis(ethoxycarbonyl)-5-dimethoxyphosphorylmethylidene-1,3-oxazoline 
• 1379481-82-9 (Z)-2-(p-chlorophenyl)-4,4-bis(ethoxycarbonyl)-5-dimethoxyphosphorylmethylidene-1,3-oxazoline 
• 90098-04-7 rebamipide 
• 81917-94-4 2-(4-Chloro-benzoylamino)-2-vinyl-malonic acid diethyl ester 

Relevant articles and documents

Phenyl and Diaryl Ureas with Thiazolo[5,4-d]pyrimidine Scaffold as Angiogenesis Inhibitors: Design, Synthesis and Biological Evaluation

Angiogenesis is crucial for tumor growth and inhibition of angiogenesis has been regarded as a promising approach for cancer therapy. Vascular endothelial growth factor receptor-2 (VEGFR-2) is an important factor in angiogenesis. In this work, a novel series of thiazolo[5,4-d]pyrimidine derivatives inhibiting angiogenesis were rationally designed and synthesized. Their inhibitory activities against human umbilical vein endothelial cells (HUVEC) were investigated in vitro. 1-(4-Fluorophenyl)-3-{4-[(5-methyl-2-phenyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl)amino]phenyl}urea (19b) and 1-(3-Fluorophenyl)-3-{4-[(5-methyl-2-phenyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl)amino]phenyl}urea (19g) exhibited the most potent inhibitory effect on HUVEC proliferation (IC50=12.8 and 5.3 μm, respectively). Compound 19g could inhibit the migration of human umbilical vein endothelial cells. These results support the further investigation of these compounds as potent anticancer agents.

Diarylureas and Diarylamides with Oxazolo[5,4-d]pyrimidine Scaffold as Angiogenesis Inhibitors

A series of oxazolopyrimidine-based ureas and amides were designed, synthesized, and biologically evaluated for their antiproliferative and antiangiogenic activities. These compounds were identified to exhibit inhibitory activities against human umbilical vein endothelial cells (HUVEC) in vitro. Among these compounds, compound 22 effectively inhibited the migration and capillary-like tube formation of human umbilical vein endothelial cells. It also exhibited a concentration-dependent inhibition on capillary sprouting from the rat aorta rings. Preliminary mechanistic studies revealed that compound 22 suppressed protein kinases activation, by decreasing PI3K and ERK 1/2 phosphorylation. These results support the further investigation of this class of compounds as potential anticancer agents.

Process for preparing 2-(4-chlorobenzolamino)-3[ (1h)-quinolinon-4-yl] propionic acid

The invention relates to a novel method for preparing 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid, also known as Rebamipide represented by the formula I and useful for treatment of peptic ulcer from alkyl 2-(4-chlorobenzoylamino)-2-alkoxycarbonyl-3-[2(1H)-quinolinon-4-yl]propionate represented by the formula II in the presence of a base solution for hydrolysis and decarboxylation to remove a carboxyl group.