120386-12-1

Basic information

• Product Name: 4-amino-7-[(2-hydroxyethoxy)methyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbohydrazide
• Synonyms: 7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid, 4-amino-7-[(2-hydroxyethoxy)methyl]-, hydrazide
• CAS NO: 120386-12-1
• Molecular Formula: C₁₀H₁₄N₆O₃
• Molecular Weight: 266.2566
• Mol File: 120386-12-1.mol
• Article Data: 1

Chemical Properties

• Density: 1.7g/cm³
• Refractive Index: 1.749
• CAS DataBase Reference: 4-amino-7-[(2-hydroxyethoxy)methyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-7-[(2-hydroxyethoxy)methyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbohydrazide(120386-12-1)
• EPA Substance Registry System: 4-amino-7-[(2-hydroxyethoxy)methyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbohydrazide(120386-12-1)

Safety Data

• Hazardous Substances Data: 120386-12-1(Hazardous Substances Data)

Upstream product

• 120386-04-1 4-amino-5-cyano-7-<(2-acetoxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine 
• 120386-06-3 2-amino-5-cyano-7-<(2-hydroxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine 
• 19393-83-0 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine 
• 120386-10-9 4-amino-7-<(2-hydroxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine-5-formimidate 

Relevant articles and documents

Synthesis, Cytotoxicity, and Antiviral Activity of Certain 7-pyrrolopyrimidine Nucleosides Related to Toyocamycin and Sangivamycin

A number of 7-pyrrolopyrimidine derivatives related to the nucleoside antibiotics toyocamycin and sangivamycin were prepared and tested for their biological activity.Treatment of the sodium salt of 4-amino-6-bromo-5-cyanopyrrolopyrimidine (1) with (2-acetoxyethoxy)methyl bromide (2) afforded a mixture of 4-amino-6-bromo-5-cyano-7-pyrrolopyrimidine (3) and the corresponding N1 isomer.Debromination of this mixture gave the corresponding 4-amino-5-cyano-7-pyrrolopyrimidine (4) and 4-amino-5-cyano-1-pyrrolopyrimidine (5).Deacetylation of 4 and 5 furnished 4-amino-5-cyano-7-pyrrolopyrimidine (6) and the corresponding N1 isomer (7), respectively.The sites of attachment for the acyclic moiety for 6 and 7 were assigned on the basis of UV spectral studies as well as (13)C NMR spectroscopy.Conventional functional group transformation of 6 provided a number of novel 5-substituted derivatives (8-10), including the sangivamycin derivative 8.The methyl formimidate derivative 10 was converted to the thioamid derivative 11 and the carbohydrazide derivative 12.Compounds 6 and 8-12 were tested for cytotoxicity to L1210 murine leukemic cells in vitro.None of these compounds caused significant inhibition of cell growth.Evaluation of compounds 4 and 6-12 for activity against human cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1) revealed that only the thioamide (11) was active.It inhibited HCMV but not HSV-1 at concentrations producing only slight cytotoxicity in the human foreskin fibroblasts (HFF cells) and KB cells.