150869-42-4

Basic information

• Product Name: 2-Propenoic acid, 3-(2-amino-4-chlorophenyl)-, methyl ester, (2E)-
• CAS NO: 150869-42-4
• Molecular Formula: C10H10ClNO2
• Molecular Weight: 211.648
• Mol File: 150869-42-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(2-amino-4-chlorophenyl)-, methyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(2-amino-4-chlorophenyl)-, methyl ester, (2E)-(150869-42-4)
• EPA Substance Registry System: 2-Propenoic acid, 3-(2-amino-4-chlorophenyl)-, methyl ester, (2E)-(150869-42-4)

Safety Data

• Hazardous Substances Data: 150869-42-4(Hazardous Substances Data)

Upstream product

• 823-57-4 2-bromo-5-chloroaniline 
• 292638-85-8 acrylic acid methyl ester 
• 108-42-9 3-chloro-aniline 
• 5551-11-1 4-Chloro-2-nitrobenzaldehyde 
• 6828-35-9 5-chloro-2-iodoaniline 
• 150869-41-3 methyl (E)-3-(4-chloro-2-nitrophenyl)acrylate 

Downstream Products

• 868407-32-3 (E)-(5-chloro-2-{3-[3-(4-fluorobenzyl)-3,9-diazabicyclo[3.3.1]non-9-yl]-3-oxopropenyl}phenyl)-carbamic acid tert-butyl ester 
• 868407-38-9 (E)-2-chloro-N-(5-chloro-2-{3-[3-(4-fluorobenzyl)-3,9-diazabicyclo[3.3.1]non-9-yl]-3-oxopropenyl}-phenyl)acetamide 
• 868408-12-2 (E)-(5-chloro-2-{3-[9-(4-fluorobenzyl)-3-oxa-7,9-diazabicyclo[3.3.1]non-7-yl]-3-oxopropenyl}-phenyl)-carbamic acid tert-butyl ester 
• 868408-15-5 (E)-(5-chloro-2-{3-[7-(4-fluorobenzyl)-3-oxa-7,9-diazabicyclo[3.3.1]non-9-yl]-3-oxopropenyl}-phenyl)-carbamic acid tert-butyl ester 
• 868406-31-9 (E)-(5-chloro-2-{3-[8-(4-fluorobenzyl)-3,8-diazabicyclo[3.2.1]oct-3-yl]-3-oxopropenyl}phenyl)-carbamic acid tert-butyl ester 
• 868406-52-4 (E)-(5-chloro-2-{3-[8-(4-fluorobenzyl)-3,8-diazabicyclo[3.2.1]oct-3-yl]-3-oxopropenyl}-phenyl)-urea 
• 231295-97-9 methyl trans-4-chloro-2-(ethoxycarbonylamino)cinnamate 
• 231296-58-5 methyl trans-4-chloro-2-[(phenylsulfonyl)amino]cinnamate 
• 685534-21-8 (E)-3-(2-tert-butoxycarbonylamino-4-chlorophenyl)-acrylic acid methyl ester 
• 150869-43-5 (E)-3-[4-Chloro-2-(2-nitro-acetylamino)-phenyl]-acrylic acid methyl ester 

Relevant articles and documents

Stereoselective construction of deoxy-cruciferane alkaloids by NHC-catalyzed intramolecular annulation of homoenolate with quinazolinone

Chiral N-heterocyclic carbene (NHC)-catalyzed intramolecular [3 + 2] annulation of enals with an unactivated imine moiety of quinazolinone via formal homoenolate cycloaddition has been demonstrated. It is an excellent approach for stereoselective syntheses of deoxy-cruciferane alkaloids comprising a biologically important pyrroloindoline scaffold. Notably, this is the first report on the NHC-catalyzed asymmetric intramolecular homoenolate annulation with cyclic N-acyl amidine.

Bioisosteric modifications of 2-arylureidobenzoic acids: Selective noncompetitive antagonists for the homomeric kainate receptor subtype GluR5

2-Arylureidobenzoic acids (AUBAs) have recently been presented as the first series of selective noncompetitive GluR5 antagonists. In this paper we have modified the acidic moiety of the AUBAs by introducing different acidic and neutral groups, and similarly, we have replaced the urea linker of the AUBAs with other structurally related linkers. Replacing the acid with neutral substituents led to inactive compounds in all instances, showing that an acidic moiety is necessary for activity. Replacing the carboxylic moiety in 2a with a sulfonic acid (5c) or a tetrazole ring (5d) improved the potency at GluR5 receptors (compounds 5c and 5d showed IC50 values of 1.5 and 2.0 μM, respectively, compared to compound 2a with IC50 = 4.8 μM). Compound 5c did not show improved in vivo activity in the ATPA rigidity test compared to 2a, whereas compound 5d was 4 times more potent than 2a. All compounds wherein the urea linker had been replaced showed lower or no activity. The results described extend the knowledge of structure-activity relationships for the AUBAs, and compound 5d may prove to be a good candidate for studying GluR5 receptors in vitro and in vivo.

3-nitro-3,4-dihydro-2(1H)-quinolones - Excitatory amino acid antagonists acting at glycine-site NMDA and (RS)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors

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