14365-44-7

Basic information

• Product Name: 5'-AMINOADENOSINE
• Synonyms: 5'-AMINOADENOSINE;5'-NH-ADO;5’-amino-5’-deoxyadenosine;5'-AMINO-5'-DEOXY-D-ADENOSINE;5'-Deoxy-5'-aminoadenosine;Adenosine, 5'-amino-5'-deoxy- (8ci)(9ci);Nsc 238990;Adenosine,5'-aMino-5'-deoxy-
• CAS NO: 14365-44-7
• Molecular Formula: C₁₀H₁₄N₆O₃
• Molecular Weight: 266.26
• Mol File: 14365-44-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 647.6 °C at 760 mmHg
• Flash Point: 345.4 °C
• Appearance: /
• Density: 2.08 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 5'-AMINOADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-AMINOADENOSINE(14365-44-7)
• EPA Substance Registry System: 5'-AMINOADENOSINE(14365-44-7)

Safety Data

• Hazardous Substances Data: 14365-44-7(Hazardous Substances Data)

Usage

Uses

5''-Amino-5''-deoxyadenosine is an adenosine kinase inhibitor.

Upstream product

• 68144-26-3 5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine 
• 40653-96-1 N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-methylsulfonyladenosine 
• 220579-81-7 2-[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-isoindole-1,3-dione 
• 892-48-8 5'-deoxy-5'-chloroadenosine 
• 58-61-7 adenosine 
• 80860-44-2 2-[[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl]-2,3-dihydro-1H-isoindol-1,3-dione 
• 362-75-4 2',3'-isopropylidene adenosine 
• 4546-55-8 N-benzoyladenosine 
• 57610-04-5 N⁶-benzoyl-5'-azidoadenosine 
• 21950-36-7 5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine 
• 737-76-8 5'-azido-5'-deoxyadenosine 

Downstream Products

• 108257-20-1 (3-{[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamoyl}-propyl)-carbamic acid benzyl ester 
• 108257-19-8 (2-{[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamoyl}-ethyl)-carbamic acid benzyl ester 
• 121683-10-1 5'-(4-carboxyphenylsulphonamido)-5'-deoxyadenosine potassium salt 
• 108257-24-5 (7-{[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamoyl}-heptyl)-carbamic acid benzyl ester 
• 108257-21-2 (4-{[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamoyl}-butyl)-carbamic acid benzyl ester 
• 108257-22-3 (5-{[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamoyl}-pentyl)-carbamic acid benzyl ester 
• 108257-23-4 (6-{[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamoyl}-hexyl)-carbamic acid benzyl ester 
• 213554-34-8 N-benzyloxycarbonyl-N'-(2',3'-O-isopropylidene-5'-deoxyadenosin-5'-yl)sulfamide 

Relevant articles and documents

Screening and in situ synthesis using crystals of a NAD kinase lead to a potent antistaphylococcal compound

Making new ligands for a given protein by in situ ligation of building blocks (or fragments) is an attractive method. However, it suffers from inherent limitations, such as the limited number of available chemical reactions and the low information content of usual chemical library deconvolution. Here, we describe a focused screening of adenosine derivatives using X-ray crystallography. We discovered an unexpected and biocompatible chemical reactivity and have simultaneously identified the mode of binding of the resulting products. We observed that the NAD kinase from Listeria monocytogenes (LmNADK1) can promote amide formation between 5′-amino-5′- deoxyadenosine and carboxylic acid groups. This unexpected reactivity allowed us to bridge in situ two adenosine derivatives to fully occupy the active NAD site. This guided the design of a close analog showing micromolar inhibition of two human pathogenic NAD kinases and potent bactericidal activity against Staphylococcus aureus in vitro.

Diadenosine antibacterial compounds

The present invention relates to compounds of formula (I): wherein R1, R2, R3, R4, X1, X2, X3 and Z are as defined in claim 1.The compounds are useful in the prevention and/or treatment of bacterial infections.

Efficient reduction of azides to amines with tributylstannane. High-yield syntheses of amino and diamino deoxynucleosides

Treatment of unprotected azido-deoxynucleosides with tributylstannane/AIBN in hot benzene/DMAC (or silyl-protected derivatives in benzene) resulted in formation of the corresponding amino-deoxynucleosides in high isolated yields. A radical process is indicated.