214416-39-4

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-CHLORO-PHENYL)-5-METHYL-2H-PYRAZOL-3-YLAMINE is used as a building block for the synthesis of new drugs due to its potential to contribute to the development of bioactive molecules with therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 4-(4-CHLORO-PHENYL)-5-METHYL-2H-PYRAZOL-3-YLAMINE is used as a key intermediate for creating a variety of chemical compounds, leveraging its reactive functional groups for further chemical transformations.

Upstream product

• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 140-53-4 p-chlorobenzyl cyanide 
• 5219-07-8 2-(4-chlorophenyl)-3-oxobutanenitrile 

Downstream Products

• 214416-33-8 3-(4-Chloro-phenyl)-2,5-dimethyl-4H-pyrazolo[1,5-a]pyrimidin-7-one 
• 879450-15-4 3-(4-chloro-phenyl)-5-methoxymethyl-2-methyl-pyrazolo[1,5-a]pyrimidin-7-ol 
• 1363292-99-2 3-(4-chlorophenyl)-7-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one 
• 1363293-03-1 3-(4-chlorophenyl)-7-(3-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one 
• 897769-21-0 7-chloro-3-(4-chloro-phenyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine 
• 906765-93-3 3-(4-chloro-phenyl)-5-ethyl-2-methyl-pyrazolo[1,5-a]pyrimidin-7-ol 
• 1363280-50-5 (S)-(1-(3-(4-chlorophenyl)-7-(3-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)methanol 
• 1363280-48-1 (S)-(1-(3-(4-chlorophenyl)-7-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-yl)methanol 

Relevant academic research and scientific papers

Structure and tautomerism of 4-substituted 3(5)-aminopyrazoles in solution and in the solid state: NMR study and Ab initio calculations

Annular tautomerism of 3(5)-aminopyrazoles containing a cyano, thiocyanato, or aryl substituent in the 4-position has been studied by 1H and 13C NMR in solution, cross-polarization and magic-angle spinning 13C NMR in the s

N -Acetyl-3-aminopyrazoles block the non-canonical NF-kB cascade by selectively inhibiting NIK

NF-κB-inducing kinase (NIK), an oncogenic drug target that is associated with various cancers, is a central signalling component of the non-canonical pathway. A blind screening process, which established that amino pyrazole related scaffolds have an effect on IKKbeta, led to a hit-to-lead optimization process that identified the aminopyrazole 3a as a low μM selective NIK inhibitor. Compound 3a effectively inhibited the NIK-dependent activation of the NF-κB pathway in tumour cells, confirming its selective inhibitory profile.

Pyrazolopyrimidines as Potent Stimulators for Transient Receptor Potential Canonical 3/6/7 Channels

Transient receptor potential canonical 3/6/7 (TRPC3/6/7) are highly homologous receptor-operated nonselective cation channels. Despite their physiological significance, very few selective and potent agonists are available for functional examination of these channels. Using a cell-based high throughput screening approach, a lead compound with the pyrazolopyrimidine skeleton was identified as a TRPC6 agonist. Synthetic schemes for the lead and its analogues were established, and structural-activity relationship studies were carried out. A series of potent and direct agonists of TRPC3/6/7 channels were identified, and among them, 4m-4p have a potency order of TRPC3 > C7 > C6, with 4n being the most potent with an EC50 of 20 nM on TRPC3. Importantly, these compounds exhibited no stimulatory activity on related TRP channels. The potent and selective compounds described here should be suitable for evaluation of the roles of TRPC channels in the physiology and pathogenesis of diseases, including glomerulosclerosis and cancer.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

Optimization of 3-phenylpyrazolo[1,5-a]pyrimidines as potent corticotropin-releasing factor-1 antagonists with adequate lipophilicity and water solubility

In our efforts to identify potent CRF1 antagonists with proper physicochemical properties, a series of 3-phenylpyrazolo[1,5-a]pyrimidines bearing polar groups, such as amino, hydroxyl, methoxy, sulfoxide, were designed and synthesized. Several positions of the core structure were identified, where a polar group was tolerated with slight reduction in receptor binding. NBI 30545 (18n) was found to have good binding affinity and potent antagonistic activity at the human CRF1 receptor. Moreover, this compound had proper lipophilicity (logD=2.78) and good solubility in water (>10mg/mL), and exhibited good plasma and brain exposure when given orally.

The discovery of 4-(3-pentylamino)-2,7-dimethyl-8-(2-methyl-4- methoxyphenyl)-pyrazolo-[1,5-a]-pyrimidine: A corticotropin-releasing factor (hCRF1) antagonist

Structure-activity relationship studies led to the discovery of 4-(3- pentylamino)-2,7-dimethyl-8-(2-methyl-4-methoxyphenyl)-pyrazolo-[1,5-a]- pyrimidine 11-31 (DMP904), whose pharmacological profile strongly supports the hypothesis that hCRF1 antagonists may be potent anxiolytic drugs. Compound 11-31 (hCRF1 K(i) = 1.0 ± 0.2 nM (n = 8)) was a potent antagonist of hCRF1-coupled adenylate cyclase activity in HEK293 cells (IC50 = 10.0 ± 0.01 nM versus 10 nM r/hCRF, n = 8); α-helical CRF(9-41) had weaker potency (IC50 = 286 ± 63 nM, n = 3). Analogue 11-31 had good oral activity in the rat situational anxiety test; the minimum effective dose for 11-31 was 0.3 mg/kg (po). Maximal efficacy (approximately 57% reduction in latency time in the dark compartment) was observed at this dose. Chlordiazepoxide caused a 72% reduction in latency at 20 mg/kg (po). The literature compound 1 (CP154526-1, 30 mg/kg (po)) was inactive in this test. Compound 11-31 did not inhibit open-field locomotor activity at 10, 30, and 100 mg/kg (po) in rats. In beagle dogs, this compound (5 mg/kg, iv, po) afforded good plasma levels. The key iv pharmacokinetic parameters were t(1/2), CL and V(d,ss) values equal to 46.4 ± 7.6 h, 0.49 ± 0.08 L/kg/h and 23.0 ± 4.2 L/kg, respectively. After oral dosing, the mean C(max), T(max), t(1/2) and bioavailability values were equal to 1260 ± 290 nM, 0.75 ± 0.25 h, 45.1 ± 10.2 h and 33.1%, respectively. The overall rat behavioral profile of this compound suggests that it may be an anxiolytic drug with a low motor side effect liability. (C) 2000 Elsevier Science Ltd.