614726-85-1

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylis used as a pharmaceutical compound for the development of treatments for diseases associated with neuronal dendritic abnormalities. As a novel cannabinoid CB1 receptor neutral antagonist, it can reverse the effects of the CB1 agonist AM411, making it a promising candidate for therapeutic applications in this area.
Used in Chemical Research:
1H-Pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylcan also be used in chemical research as a starting material or intermediate for the synthesis of other complex organic compounds. Its unique structure and functional groups make it a valuable building block for the development of new molecules with potential applications in various industries.
Used in Material Science:
1H-Pyrazole-3-carboxamide,
5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylmay also find applications in material science, particularly in the development of new materials with specific properties. Its chemical structure and functional groups could be exploited to create materials with unique characteristics, such as improved stability, reactivity, or selectivity in various chemical processes.

Biological Activity

am4113, a pyrazole analog structurally related to sr141716 and am251, is a novel cannabinoid cb1 neutral antagonist. am4113 suppressed food intake and food-reinforced behavior in rats.

in vitro

am4113 was able to bind with high affinity to cb1 receptors, exhibiting 100-fold selectivity for cb1 against cb2 receptors. the ki value for cb1 was 0.897 ± 0.44 nm, while the ki value for hcb2 was 92 ± 6.9 nm [1].

in vivo

in rats, treatment with am4113 (2.0 and 4.0 mg/kg) attenuated the am411-induced locomotor suppression and analgesia. in addition, 4.0 mg/kg am4113 alone significantly suppressed locomotor activity when compared with vehicle. am4113 dose-dependently decreased lever pressing on an fr1 schedule. am4113 produced conditioned taste avoidance and suppression of ingestive (hedonic) taste reactivity scores in a dose-dependent manner [1]. am4113 didn’t induce signs of nausea [1].

references

[1] sink k s, mclaughlin p j, wood j a t, et al. the novel cannabinoid cb1 receptor neutral antagonist am4113 suppresses food intake and food-reinforced behavior but does not induce signs of nausea in rats[j]. neuropsychopharmacology, 2008, 33(4): 946-955.

Upstream product

• 168272-78-4 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid methyl ester 
• 124-41-4 sodium methylate 
• 168273-05-0 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride 
• 6285-05-8 4'-chloropropiophenone 
• 158941-22-1 ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate 
• 169544-41-6 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutyric acid ethyl ester 
• 162758-35-2 rimonabant acid 

Downstream Products

• 681179-07-7 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonitrile 
• 1072113-07-5 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(2-propylpentanoyl)-1H-pyrazole-3-carboxamide 
• 1072113-01-9 5-(4-chlorophenyl)-N-(cyclopentanecarbonyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-06-4 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(3,3-dimethylbutanoyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-05-3 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(2,2-dimethylbutanoyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-11-1 5-(4-chlorophenyl)-N-(cycloheptylcarbamoyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-15-5 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(phenylcarbamoyl)-1H-pyrazole-3-carboxamide 
• 1072113-19-9 tert-butyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonylcarbamate 
• 1072113-20-2 neopentyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonylcarbamate 
• 1072113-10-0 5-(4-chlorophenyl)-N-(cyclohexylcarbamoyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-02-0 N-acetyl-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-04-2 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-isobutyryl-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-03-1 N-butyryl-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-18-8 butyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl carbamate 

Relevant academic research and scientific papers

"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.

MMPL3 INHIBITORS, COMPOSITIONS AND USES THEREOF

Disclosed are inhibitors of mycobacterial membrane protein MmpL3, compositions comprising the inhibitors, and methods of preparation and use thereof.

Synthesis and structure-activity relationship of novel diarylpyrazole imide analogues as CB1 cannabinoid receptor ligands

A myriad of research groups have been engaged in searching for novel CB1 receptor antagonists, since SR141716A (rimonabant), a CB1 receptor antagonist, was discovered for an obesity treatment. In this research, extended series, based on the 1,5-diarylpyra

Azole Derivatives as Cannabinoid CB1 Receptor Antagonists

A novel azole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disor

Tetrazole-biarylpyrazole derivatives as cannabinoid CB1 receptor antagonists

Cannabinoid CB1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and related metabolic disorders were reported in 2001. To further evaluate the properties of CB recep

Bioisosteric replacement of the pyrazole 3-carboxamide moiety of rimonabant. A novel series of oxadiazoles as CB1 cannabinoid receptor antagonists

Based on the bioisosteric replacement of the pyrazole C3-carboxamide of rimonabant with a 5-alkyl oxadiazole ring, a novel class of oxadiazole derivatives with promising biological activity towards CB1 receptors was discovered. Among them, compounds with an alkyl linker containing a strong electron-withdrawing group (e.g., CF3) and a sterically favorable bulky group (e.g., t-butyl) exhibited excellent CB1 antagonism and selectivity, and thus might serve as potential candidates for further development as anti-obesity agents.

(1,5-DIPHENYL-1H-PYRAZOL-3-YL)OXADIAZOLE DERIVATIVES, PREPARATION METHOD THEREOF AND USE OF SAME IN THERAPEUTICS

The invention relates to compounds having formula (I): Wherein R1, R2, R3 and R4 are as defined herein. The invention also relates to a method of preparing said compounds and to the application thereof in therapeutics.

Cannabinoid receptor ligands and uses thereof

Compounds of Formula (I) that act as cannabinoid receptor ligands and their uses in the treatment of diseases linked to the modulation of the cannabinoid receptors in animals are described herein.