Description

A number of 3,4-disubstituted pyrazolo[3,4-d]pyrimidine ribonucleosides were synthesized and tested for their biological activity. Glycosylation of persilylated as well as nonsilylated 3-bromoallopurinol with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (4) provided the key intermediate 3-bromo-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrazolo[3,4-d]pyrimidin -4(5H)-one (5a). Similar glycosylations of 3-cyanoallopurinol and 3-(methylthio)allopurinol furnished the corresponding protected N-1 glycosyl derivatives (5b and 5c). Debenzoylation of these nucleosides (5a-c) gave the corresponding 3-bromo, 3-cyano-, and 3-(methylthio)allopurinol nucleosides (6a-c). The site of glycosylation and anomeric configuration of 6a and 6c were assigned on the basis of spectral studies as well as conversion to allopurinol ribonucleoside, whereas the structural assignment of 6b was made by single-crystal X-ray analysis. Conventional functional group transformation of 5a and 5b provided a number of novel 3-substituted allopurinol nucleosides, which included 18a-d. Glycosylation of 4-amino-3-bromopyrazolo[3,4-d]pyrimidine with 4 and subsequent debenzoylation gave 3-bromo-4-aminopyrazolo[3,4-d]pyrimidine ribonucleoside from which 3,4-diamino-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidine was obtained by amination. Thiation of 5b, followed by deblocking, gave 3-cyanothiopurinol ribonucleoside (20). All of these compounds were tested in vitro against certain viruses, tumor cells, and the parasite Leishmania tropica. Among the 3-substituted allopurinol nucleosides, 18b and 18c showed significant activity against Para 3 virus and were found to be potent inhibitors of growth of L1210 and P388 leukemia. Compound 20 exhibited the most significant broad-spectrum in vitro antiviral and antitumor activity. 3-Bromoallopurinol ribonucleoside (6a) was found to be more active than allopurinol ribonucleoside against Leishmania tropica within human macrophages in vitro.

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3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine (83255-86-1) Specifications

CAS	83255-86-1
CAS Min %	97%
CAS Max %	100%
MDL Number	MFCD12196922
InChI Key	GZQVGSRUUTUJNG-UHFFFAOYSA-N
Chemical Name or Material	3-Bromo-1h-pyrazolo[3,4-d]pyrimidin-4-amine
Infrared Spectrum	Authentic
Physical Form	Powder or Chunks
Packaging	Glass bottle
Molecular Formula	C5H4BrN5
Molecular Weight (g/mol)	214.026
SMILES	C1=NC2=NNC(=C2C(=N1)N)Br
Color
Melting Point	350°C(lit.)
Assay	97%~100%

 

3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine (83255-86-1) Safety and Handling

(83255-86-1) Hazard description:

♦ Causes skin irritation

♦ Causes serious eye irritation.

3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine Precautionary statement:

♦ Wash hands and face thoroughly after handling.

♦ Wear protective gloves, eye protection

♦ If on skin: Wash with plenty of soap and water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.

♦ If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

WARNING: The information provided on this web site was developed in compliance with European Union (EU) regulations and is correct to the best of our knowledge, information and belief at the date of its publication. The information given is designed only as a guide for safe handling and use. It is not to be considered as either a warranty or quality specification.

3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine (83255-86-1) Articles

Bromopyrazolo[3,4-d]pyrimidine 2′-deoxy-2′-fluoro-β-D-arabinonucleosides: Modified DNA constituents with an unusually rigid sugar N-conformation

Journal of Organic Chemistry 2003

Synthesis, anticancer evaluation, and molecular docking studies of some novel 4,6-disubstituted pyrazolo[3,4-d]pyrimidines as cyclin-dependent kinase 2 (CDK2) inhibitors

Bioorganic Chemistry 2018

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