142981-80-4

Basic information

• Product Name: 3-amino-1-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-methylthio-1H-pyrazole-4-carbonitrile
• CAS NO: 142981-80-4
• Molecular Weight: 506.582
• Mol File: 142981-80-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-amino-1-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-methylthio-1H-pyrazole-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-amino-1-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-methylthio-1H-pyrazole-4-carbonitrile(142981-80-4)
• EPA Substance Registry System: 3-amino-1-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-methylthio-1H-pyrazole-4-carbonitrile(142981-80-4)

Safety Data

• Hazardous Substances Data: 142981-80-4(Hazardous Substances Data)

Upstream product

• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 72760-85-1 5-amino-3-(methylsulfanyl)-1H-pyrazole-4-carbonitrile 

Relevant articles and documents

Synthesis and Properties of Methylthiopyrazolopyrimidine 2'-Deoxy-&β-D-ribonucleosides

The synthesis of the 3- and 4-(methylthio)pyrazolopyrimidine N1- and N2-2'-deoxy-β-D-ribonucleosides 2b, 15 is described.Anionic glycosylation of 5-amino-3-(methylthio)-4-pyrazolecarbonitrile (4) or 4-(methylthio)pyrazolopyrimidine (12) with 2-desoxy-3,5-di-O-(4-methylbenzoyl)-α-D-erythro-pentofuranosyl chloride (5) gave the regioisomeric N1- and N2-nucleosides 6, 7, 13, and 14.The N1 isomer was the main product in the reaction of 12, and the N2 compound was the preferred product in the glycosylation of 4.Glycosylation in suspension (12) yielded an appreciable amount of the N2 α-D-isomer 16. 4-Aminopyrazolopyrimidine 2'-deoxyribonucleosides 3a, b with a methylthio group at C-3 are resistant to deamination by adenosine deaminase and inhibit the proliferation of leukemia cell lines. Key Words: Pyrazolopyrimidine / Pyrazoles / 2'-Deoxyribonucleosides / Glycosylation / Cytotoxicity