1015765-46-4

Basic information

• Product Name: ethyl 5-amino-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate
• Synonyms: ethyl 5-amino-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate
• CAS NO: 1015765-46-4
• Molecular Weight: 314.171
• Mol File: 1015765-46-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ethyl 5-amino-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-amino-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate(1015765-46-4)
• EPA Substance Registry System: ethyl 5-amino-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate(1015765-46-4)

Safety Data

• Hazardous Substances Data: 1015765-46-4(Hazardous Substances Data)

Upstream product

• 5446-18-4 2,4-dichlorophenyl hydrazine hydrochloride 
• 68350-64-1 potassium 3-cyano-1-ethoxy-1-oxobut-2-en-2-olate 

Downstream Products

• 1015765-56-6 ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxylate 
• 1015765-57-7 ethyl 1-(2,4-dichlorophenyl)-5-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methyl-1H-pyrazole-3-carboxylate 
• 1345992-64-4 ethyl 5-(2-chloro-1H-pyrrol-1-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate 
• 1345992-66-6 ethyl 5-(2,5-dichloro-1H-pyrrol-1-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate 
• 1345992-39-3 5-(2-chloro-1H-pyrrol-1-yl)-N-(3,4-dichlorobenzyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1345992-74-6 5-(2-chloro-1H-pyrrol-1-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid 
• 1345992-76-8 5-(2,5-dichloro-1H-pyrrol-1-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid 
• 1345992-40-6 5-(2-chloro-1H-pyrrol-1-yl)-N-cyclohexyl-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1345992-78-0 1-(2,4-dichlorophenyl)-4-methyl-5-(4,5,6,7-tetrahydro-2H-isoindol-2-yl)-1H-pyrazole-3-carboxylic acid 
• 1345992-41-7 5-(2,5-dichloro-1H-pyrrol-1-yl)-N-(3,4-dichlorobenzyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1345992-42-8 N-cyclohexyl-5-(2,5-dichloro-1H-pyrrol-1-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1345992-43-9 N-(3,4-dichlorobenzyl)-1-(2,4-dichlorophenyl)-4-methyl-5-(4,5,6,7-tetrahydroisoindol-2-yl)-1H-pyrazole-3-carboxamide 
• 1345992-44-0 N-cyclohexyl-1-(2,4-dichlorophenyl)-4-methyl-5-(4,5,6,7-tetrahydroisoindol-2-yl)-1H-pyrazole-3-carboxamide 
• 1345992-68-8 ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4,5,6,7-tetrahydro-2H-isoindol-2-yl)-1H-pyrazole-3-carboxylate 

Relevant articles and documents

"Photo-Rimonabant": Synthesis and Biological Evaluation of Novel Photoswitchable Molecules Derived from Rimonabant Lead to a Highly Selective and Nanomolar " Cis-On" CB1R Antagonist

Human cannabinoid receptor type 1 (hCB1R) plays important roles in the regulation of appetite and development of addictive behaviors. Herein, we describe the design, synthesis, photocharacterization, molecular docking, and in vitro characterization of "photo-rimonabant", i.e., azo-derivatives of the selective hCB1R antagonist SR1411716A (rimonabant). By applying azo-extension strategies, we yielded compound 16a, which shows marked affinity for CB1R (Ki (cis form) = 29 nM), whose potency increases by illumination with ultraviolet light (CB1R Kitrans/cis ratio = 15.3). Through radioligand binding, calcium mobilization, and cell luminescence assays, we established that 16a is highly selective for hCB1R over hCB2R. These selective antagonists can be valuable molecular tools for optical modulation of CBRs and better understanding of disorders associated with the endocannabinoid system.

Synthesis, cannabinoid receptor affinity, and molecular modeling studies of substituted 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides

The new 1-phenyl-5-(1H-pyrrol-1-yl)pyrazole-3-carboxamides were compared with the reference compounds AM251 and SR144528 for cannabinoid hCB1 and hCB2 receptor affinity. Compounds bearing 2,4-dichlorophenyl or 2,4-difluorophenyl groups at position 1 and 2,5-dimethylpyrrole moiety at position 5 of the pyrazole nucleus were generally more selective for hCB 1. On the other hand, the N-cyclohexyl group at the 3-carboxamide was the determinant for the hCB2 selectivity, in particular when a 3,4-dichlorophenyl group was also present at position 1. Compound 26 was the most selective ligand for the hCB1 receptor (Ki (CB 2)/Ki (CB1) = 140.7). Derivative 30, the most potent hCB1 ligand (Ki = 5.6 nM), was equipotent to AM251 and behaved as an inverse agonist in the cAMP assay (EC50 ～1 nM). The carbonyl oxygen of both 26 and 30 formed a H-bond with K3.28(192), while the substituents at the nitrogen fitted in a pocket formed by lipophilic residues. This H-bonding interaction was proposed to account for the high affinity for receptors' inactive state and the inverse agonist activity.