100524-24-1

Basic information

• Product Name: 1H-Pyrazolo[3,4-d]pyrimidine-1-ethanol, 4-amino-
• Synonyms: 2-(4-amino-pyrazolo[3,4-d]pyrimidin-1-yl)-ethanol;1H-Pyrazolo[3,4-d]pyrimidine-1-ethanol,4-amino;9-(2'-hydroxyethyl)adenine;2-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-aethanol
• CAS NO: 100524-24-1
• Molecular Formula: C7H9N5O
• Molecular Weight: 179.17900
• Mol File: 100524-24-1.mol

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazolo[3,4-d]pyrimidine-1-ethanol, 4-amino-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazolo[3,4-d]pyrimidine-1-ethanol, 4-amino-(100524-24-1)
• EPA Substance Registry System: 1H-Pyrazolo[3,4-d]pyrimidine-1-ethanol, 4-amino-(100524-24-1)

Safety Data

• Hazardous Substances Data: 100524-24-1(Hazardous Substances Data)

Usage

Chemical Class

Pyrazolo[3,4-d]pyrimidine derivatives

Usage

Pharmaceutical research and development, potential drug development

Biological Activities

Inhibition of certain enzymes and receptors

Potential Role

Treatment of various diseases and conditions, important in medicinal chemistry.

Upstream product

• 5346-53-2 5-amino-4-cyano-1-(2-hydroxyethyl)-pyrazole 
• 77287-34-4 formamide 
• 96-49-1 [1,3]-dioxolan-2-one 
• 2380-63-4 4-Aminopyrazolo<3,4-d>pyrimidin 

Relevant articles and documents

Novel, highly potent adenosine deaminase inhibitors containing the pyrazolo[3,4-d]pyrimidine ring system. Synthesis, structure-activity relationships, and molecular modeling studies

This study reports the synthesis of a number of 1- and 2-alkyl derivatives of the 4-aminopyrazolo[3,4-d]pyrimidine (APP) nucleus and their evaluation as inhibitors of ADA from bovine spleen. The 2-substituted aminopyrazolopyrimidines proved to be potent inhibitors, most of them exhibiting Ki values in the nanomolar/subnanomolar range. In this series the inhibitory activity is enhanced with the increase in length of the alkyl chain, reaching a maximum with the n-decyl substituent. Insertion of a 2′-hydroxy group in the ra-decyl chain gave 3k, whose (R)-isomer displayed the highest inhibitory potency of the series (Ki 0.053 nM), showing an activity 2 orders of magnitude higher than that of (+)-EHNA (Ki 1.14 nM), which was taken as the reference standard. Docking simulations of aminopyrazolopyrimidines into the ADA binding site were also performed, to rationalize the structure-activity relationships of this class of inhibitors.

Enantioselective synthetic thalidomide receptors based upon DNA binding motifs

A series of molecularly imprinted polymer (MIP) synthetic receptors selective for the sedative thalidomide (5) have been designed and synthesized based upon the functional monomer 9-(2′-methacryloyloxyethyl)adenine (2). 1H-NMR studies were used to establish the existence of DNA-like binding interactions between 2 and the template (5). A series of ethylene glycol dimethacrylate cross-linked copolymers was synthesized using either 2 or methacrylic acid, or a combination of these functional monomers. Zonal HPLC studies demonstrated enantioselectivity (a = 2.11) and ligand selectivity which could be attributed to the interaction of 2 with the imide moiety of 5. Compound 2 provided a more significant contribution to the binding of 5 than methacrylic acid, though a combination of these two functional monomers resulted in improved enantioselectivity. Frontal chromatographic and batch binding studies confirmed the observed differences in affinity of the imprinted and reference polymers for the template.