58347-47-0

Basic information

• Product Name: Pyrazolo[1,5-a]pyrimidine, 3-bromo-7-chloro-5-methyl-
• CAS NO: 58347-47-0
• Molecular Formula: C7H5BrClN3
• Molecular Weight: 246.49200
• Mol File: 58347-47-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 100-102 °C(Solv: ethanol (64-17-5))
• Density: 1.90±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Pyrazolo[1,5-a]pyrimidine, 3-bromo-7-chloro-5-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrazolo[1,5-a]pyrimidine, 3-bromo-7-chloro-5-methyl-(58347-47-0)
• EPA Substance Registry System: Pyrazolo[1,5-a]pyrimidine, 3-bromo-7-chloro-5-methyl-(58347-47-0)

Safety Data

• Hazardous Substances Data: 58347-47-0(Hazardous Substances Data)

Upstream product

• 16082-27-2 7-Chloro-5-methylpyrazolo[1,5-a]pyrimidine 
• 29274-35-9 5-methyl-4H-pyrazolo<1,5-a>pyrimidin-7-one 

Relevant articles and documents

Structural Insights into the Inhibition of Undecaprenyl Pyrophosphate Synthase from Gram-Positive Bacteria

The polyprenyl lipid undecaprenyl phosphate (C55P) is the universal carrier lipid for the biosynthesis of bacterial cell wall polymers. C55P is synthesized in its pyrophosphate form by undecaprenyl pyrophosphate synthase (UppS), an essentialcis-prenyltransferase that is an attractive target for antibiotic development. We previously identified a compound (MAC-0547630) that showed promise as a novel class of inhibitor and an ability to potentiate β-lactam antibiotics. Here, we provide a structural model for MAC-0547630’s inhibition of UppS and a structural rationale for its enhanced effect on UppS fromBacillus subtilisversusStaphylococcus aureus. We also describe the synthesis of a MAC-0547630 derivative (JPD447), show that it too can potentiate β-lactam antibiotics, and provide a structural rationale for its improved potentiation. Finally, we present an improved structural model of clomiphene’s inhibition of UppS. Taken together, our data provide a foundation for structure-guided drug design of more potent UppS inhibitors in the future.

Synthesis and antifungal properties of certain 7 alkylaminopyrazolo[1,5 a]pyrimidines

A series of 7-alkylaminopyrazolo[1,5-α]pyrimidines (5-25) and one 7-alkylthiopyrazolo[1,5-α]pyrimidine (4) were synthesized from the corresponding 7-chloro precursors 3, which were prepared in turn from the 7-hydroxy analogues 2, obtained via condensation of 3-aminopyrazoles with acetoacetate esters, malonate esters, or acetylenedicarboxylate ester. Compounds 4-25 were found to inhibit Trichophyton mentagrophytes (in vitro). The degree of inhibition increased with increasing 7-alkylamino chain length up to C8 units and then began to decrease with longer chain lengths. Unsaturated chains were more fungitoxic than saturated chains, 5-methyl-7-oleylaminopyrazolo[1,5-α]pyrimidine [22, R7 = NH(CH2)8 CH=CH(CH2)7CH3] being 4 times more inhibitory and 16 times more fungicidal (against T. mentagrophytes) than 5-methyl-7-n octylaminopyrazolo[1,5-α]pyrimidine [11,R7=NH(CH2)7CH3]. Although 11 and 22 appeared to have some efficacy as topical antifungal agents, when applied to T. mentagrophytes infections in vivo, both caused irritation (of abraded and unabraded guinea pig skin) as did compound 4 (R5=Me; R7=SC8H17).