897769-21-0

Basic information

• Product Name: 7-Chloro-3-(4-chlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine
• Synonyms: 7-Chloro-3-(4-chlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine
• CAS NO: 897769-21-0
• Molecular Formula: C₁₄H₁₁Cl₂N₃
• Molecular Weight: 292.17
• Mol File: 897769-21-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Chloro-3-(4-chlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Chloro-3-(4-chlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine(897769-21-0)
• EPA Substance Registry System: 7-Chloro-3-(4-chlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine(897769-21-0)

Safety Data

• Hazardous Substances Data: 897769-21-0(Hazardous Substances Data)

Upstream product

• 140-53-4 p-chlorobenzyl cyanide 
• 214416-39-4 3-methyl-4-(4-chlorophenyl)-1H-pyrazol-5-amine 
• 5219-07-8 2-(4-chlorophenyl)-3-oxobutanenitrile 
• 850764-60-2 3-(4-chloro-phenyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-ol 
• 214416-33-8 3-(4-Chloro-phenyl)-2,5-dimethyl-4H-pyrazolo[1,5-a]pyrimidin-7-one 

Relevant articles and documents

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.