960613-96-1

Basic information

• Product Name: 3-BROMO-5-CHLOROPYRAZOLO[1,5-A]PYRIMIDINE
• Synonyms: 3-BROMO-5-CHLOROPYRAZOLO[1,5-A]PYRIMIDINE
• CAS NO: 960613-96-1
• Molecular Formula: C₆H₃BrClN₃
• Molecular Weight: 232.47
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 960613-96-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 2.038 g/cm³
• Refractive Index: 1.768
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -2.51±0.40(Predicted)
• CAS DataBase Reference: 3-BROMO-5-CHLOROPYRAZOLO[1,5-A]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-5-CHLOROPYRAZOLO[1,5-A]PYRIMIDINE(960613-96-1)
• EPA Substance Registry System: 3-BROMO-5-CHLOROPYRAZOLO[1,5-A]PYRIMIDINE(960613-96-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 960613-96-1(Hazardous Substances Data)

Usage

Uses

3-Bromo-5-chloropyrazolo[1,5-A]pyrimidine shows much similarity to 4H-Pyrazolo[1,5-a]pyrimidin-7-one which is a moiety present in a variety of chemical anti-inflammatory and antischistosomal drugs.

InChI:InChI=1/C6H3BrClN3/c7-4-3-9-11-2-1-5(8)10-6(4)11/h1-3H

Upstream product

• 29274-24-6 5-chloropyrazolo[1,5-a]pyrimidine 
• 29274-22-4 pyrazolo[1,5-a]pyrimidine-5-ol 
• 29274-22-4 4H,5H-pyrazolo[1,5-a]pyrimidine-5-one 

Downstream Products

• 1084953-26-3 3-bromo-5-(2-methoxyphenyl)pyrazolo[1,5-a]pyrimidine 
• 1269646-39-0 (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-phenyloxazolidin-2-one 
• 1269646-71-0 (S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acid 
• 1269646-72-1 (S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide 
• 1269643-51-7 (S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one 
• 1269646-73-2 (S)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarbothioamide 
• 1269643-53-9 (S)-3-(3-(4-(5-amino-1,3,4-thiadiazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one 
• 1269646-74-3 (S)-N'-(1-iminoethyl)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide 
• 1269643-55-1 (S)-4-isopropyl-3-(3-(4-(5-methyl-4H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one 
• 1269646-75-4 (S)-5-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1,3,4-oxadiazol-2(3H)-one 
• 1269646-76-5 (S)-N-(2-hydroxyethyl)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarboxamide 
• 1269643-56-2 (S)-3-(3-(4-(5-(2-hydroxyethylamino)-1,3,4-oxadiazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one 
• 1269647-65-5 (S)-5-isopropyl-1-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one 
• 1269647-67-7 (S)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one 

Relevant articles and documents

Optimization of pyrazolo[1,5-a]pyrimidines lead to the identification of a highly selective casein kinase 2 inhibitor

Casein kinase 2 (CK2) is a constitutively expressed serine/threonine kinase that has a large diversity of cellular substrates. Thus, CK2 has been associated with a plethora of regulatory functions and dysregulation of CK2 has been linked to disease development in particular to cancer. The broad implications in disease pathology makes CK2 an attractive target. To date, the most advanced CK2 inhibitor is silmitasertib, which has been investigated in clinical trials for treatment of various cancers, albeit several off-targets for silmitasertib have been described. To ascertain the role of CK2 inhibition in cancer, other disease and normal physiology the development of a selective CK2 inhibitor would be highly desirable. In this study we explored the pyrazolo [1,5-a]pyrimidine hinge-binding moiety for the development of selective CK2 inhibitors. Optimization of this scaffold, which included macrocyclization, led to IC20 (31) a compound that displayed high in vitro potency for CK2 (KD = 12 nM) and exclusive selectivity for CK2. X-ray analysis revealed a canonical type-I binding mode for IC20 (31). However, the polar carboxylic acid moiety that is shared by many CK2 inhibitors including silmitasertib was required for potency but limits the cellular activity of IC20 (31) and the cellular IC50 dropped to the low micromolar range. In summary, IC20 (31) represents a highly selective and potent inhibitor of CK2, which can be used as a tool compound to study CK2 biology and potential new applications for the treatment of diseases.

Trk-INHIBITING COMPOUND

The present invention provides a drug containing a compound having Trk-inhibiting activity as an active ingredient in prophylaxis and/or therapy for Trk-related diseases such as pain, pruritus, lower urinary tract dysfunction, asthma, allergic rhinitis, inflammatory bowel disease or Chagas disease. A compound represented by the general formula (I): wherein all symbols represent the same meanings as described in the specification, a salt thereof, an N-oxide thereof, a solvate thereof or a prodrug thereof is useful as a drug component having Trk-inhibiting activity in prophylaxis and/or therapy of diseases such as pain, pruritus, lower urinary tract dysfunction, asthma, allergic rhinitis, inflammatory bowel disease or Chagas disease.

SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINE COMPOUNDS AS mTOR INHIBITORS

Compounds of Formula I: and salts thereof in which R1, R2, R2a, R3, n, X and ring B have the meanings given in the specification, are inhibitors of mTOR and are useful in the treatment of diseases which are sensitive to inhibition of mTOR, such as cancers.