75763-51-8

Basic information

• Product Name: 2'-amino-2'-deoxyinosine
• Synonyms: 2'-AMino-2'-deoxyinosine,2'-NH2-dI;2'-NH2-dI
• CAS NO: 75763-51-8
• Molecular Formula: C11H14N4O3
• Molecular Weight: 250.25
• Mol File: 75763-51-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 710.5 °C at 760 mmHg
• Flash Point: 383.5 °C
• Appearance: Off-white to Yellow/Powder
• Density: 2.08 g/cm³
• PKA: 8.92±0.70(Predicted)
• CAS DataBase Reference: 2'-amino-2'-deoxyinosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-amino-2'-deoxyinosine(75763-51-8)
• EPA Substance Registry System: 2'-amino-2'-deoxyinosine(75763-51-8)

Safety Data

• Hazardous Substances Data: 75763-51-8(Hazardous Substances Data)

Usage

General Description

2'-amino-2'-deoxyinosine, also known as Adenine, is a nucleoside analog that serves as a chemical building block in DNA and RNA molecules. It is one of the four nucleobases that make up the genetic code in DNA, and it pairs with thymine in DNA and with uracil in RNA. This molecule is also a key component in the structure and function of adenosine triphosphate (ATP), which serves as the primary energy carrier in cells. Additionally, 2'-amino-2'-deoxyinosine has been used in medicinal chemistry as a starting point for the development of antiviral and anticancer drugs due to its ability to interfere with nucleic acid synthesis in certain viruses and cancer cells.

Upstream product

• 68-94-0 Allopurinol 
• 26889-39-4 1-(2-amino-2-deoxy-β-D-ribofuranosyl)uracil 
• 10414-81-0 2'-amino-2'-deoxyadenosine 

Relevant articles and documents

Adenosine analogues as selective inhibitors of glyceraldehyde-3-phosphate dehydrogenase of trypanosomatidae via structure-based drug design

In our continuation of the structure-based design of anti-trypanosomatid drugs, parasiteselective adenosine analogues were identified as low micromolar inhibitors of glyceraldehyde3-phosphate dehydrogenase (GAPDH). Crystal structures of Trypanosoma brucei, Trypanosoma cruzi, Leishmania mexicana, and human GAPDH's provided details of how the adenosyl moiety of NAD+ interacts with the proteins, and this facilitated the understanding of the relative affinities of a series of adenosine analogues for the various GAPDH's. From exploration of modifications of the naphthalenemethyl and benzamide substituents of a lead compound, N6-(1-naphthalenemethyl)-2′-deoxy-2′- (3-methoxybenzamido)adenosine (6e), N6-(substituted-naphthalenemethyl)-2′-deoxy-2′- (substituted-benzamido)adenosine analogues were investigated. N6(1 -Naphthalenemethyl)-2′-deoxy-2′-(3,5-dimethoxybenzamido)adenosine (6m), N6- [1-(3-hydroxynaphthalene)methyl]-2′-deoxy-2′- (3,5-dimethoxybenzamido)adenosine (7m), N6-[1-(3-methoxynaphthalene)methyl]-2′-deoxy-2′- (3,5-dimethoxybenzamido)adenosine (9m), N6-(2-naphthalenemethyl)-2′-deoxy-2′1- (3-methoxybenzamido)adenosine (11e), and N6-(2-naphthalenemethyl)-2′deoxy-2′- (3,5-dimethoxybenzamido)adenosine (11m) demonstrated a 2- to 3-fold improvement over 6e and a 7100- to 25000-fold improvement over the adenosine template. IC50'S of these compounds were in the range 2-12 μM for T. brucei, T. cruzi, and L. mexicana GAPDH's, and these compounds did not inhibit mammalian GAPDH when tested at their solubility limit. To explore more thoroughly the structure- activity relationships of this class of compounds, a library of 240 N6-(substituted)-2′-deoxy-2′-(amido)adenosine analogues was generated using parallel solution-phase synthesis with N6 and C2′ substituents chosen on the basis of computational docking scores. This resulted in the identification of 40 additional compounds that inhibit parasite GAPDH's in the low micromolar range. We also explored adenosine analogues containing 5′-amido substituents and found that 2′,5′-dideoxy-2′-(3,5-dimethoxybenzamido)-5′- (diphenylacetamido)adenosine (49) displays an IC50 of 60-100 μM against the three parasite GAPDH's.

Studies of nucleosides and nucleotides. LXXX. Purine cyclonucleosides. (38). Synthesis of 6-substituted purine 2'-azido- and 2'-amino-2'-deoxyribofuranosides

-