182554-04-7

Basic information

• Product Name: 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine
• Synonyms: 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine
• CAS NO: 182554-04-7
• Molecular Weight: 552.464
• Mol File: 182554-04-7.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine(182554-04-7)
• EPA Substance Registry System: 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine(182554-04-7)

Safety Data

• Hazardous Substances Data: 182554-04-7(Hazardous Substances Data)

Upstream product

• 106-45-6 para-thiocresol 
• 474266-81-4 hexaazido-hepta-O-acetyl neomycin 
• 108-24-7 acetic anhydride 
• 671809-10-2 1,3,2′,6′-tetraazidoneamine 
• 620172-08-9 acetic acid 2-[3-acetoxy-4-(4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-5-hydroxymethyl-tetrahydro-furan-2-yloxy]-4,6-diazido-3-(4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl ester 
• 108-98-5 thiophenol 
• 468065-21-6 hexaazidoneomycin B 
• 119-04-0 neomycin B 
• 3947-65-7 neomycin A 
• 25389-98-4 neomycin B sulphate 
• 15446-43-2 neamine tetrahydrochloride 

Downstream Products

• 937021-96-0 1,3,2',6'-tetraazido-5-O-methoxymethyl-6,3',4'-tri-O-acetylneamine 
• 948916-00-5 epi-5-(2-aminoethyl)-amino-1,3,2',6'-tetraazido neamine 
• 948916-01-6 epi-5-(3-aminopropyl)-amino-1,3,2',6'-tetraazido neamine 
• 948916-02-7 epi-5-(4-aminobutyl)-amino-1,3,2',6'-tetraazido neamine 
• 1383687-90-8 5-[(chlorocarbonyl)oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine 
• 1383687-49-7 3',4'-di-O-acetyl-5-[[(propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-50-0 3',4'-di-O-acetyl-6-[[( propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-51-1 5-[[(propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-52-2 6-[[(propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-55-5 5-[[(3-azidopropylamino)carbonyl]oxy]-3',4'-di-O-acetyl-1,3,2',6'-tetraazidoneamine 
• 1383687-56-6 6-[[(3-azidopropylamino)carbonyl]oxy]-3',4'-di-O-acetyl-1,3,2',6'-tetraazidoneamine 
• 1383687-57-7 5-[[(3-azidopropylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-58-8 6-[[(3-azidopropylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-61-3 6-[[(3-azidohexylamino)carbonyl]oxy]-3',4'-di-O-acetyl-1,3,2',6'-tetraazidoneamine 

Relevant articles and documents

Structure-guided discovery of a novel aminoglycoside conjugate targeting HIV-1 RNA viral genome

The dimerization initiation site (DIS) of the HIV-1 genomic RNA is a conserved stem-loop that promotes viral genome dimerization by forming a loop-loop complex. The DIS constitutes a potentially interesting target because it is crucial for several key steps of the viral replication. In this work we describe the synthesis of a rationally designed aminoglycoside conjugate that binds the HIV-1 DIS viral RNA with high specificity, as shown by an extensive in vitro binding characterization. We propose a three-dimensional model of the drug-RNA interaction that perfectly fits with binding data. Our results show the feasibility of targeting the HIV DIS viral RNA dimer and open the way to the rationale design of a new class of antiviral drugs. In addition, due to similarities between the HIV-1 DIS RNA and the bacterial aminoacyl decoding site (A site) RNA, we show that this novel aminoglycoside conjugate also binds the bacterial A site with a similar affinity as natural aminoglycoside antibiotics.

Synthesis and antibacterial activity of novel neamine derivatives: Preponderant role of the substituent position on the neamine core

A series of neamine derivatives were prepared from the cyclic carbonate and sulfate of 1,3,2′,6′-tetraazido-3′,4′,-di-O- acetylneamine. Ring opening reactions with diversely substituted amines result in the formation of the corresponding carbamates or sulfonic acids with good overall yields. The antibacterial activities of the synthesized products against E. coli (DH5α) and S. aureus (RN4220) were evaluated. With isolated single regioisomers, the preponderant effect of the 5-positions of the carbamate substituent on the neamine core was demonstrated.

Dual effect of synthetic aminoglycosides: Antibacterial activity against Bacillus anthracis and inhibition of anthrax lethal factor

Defence against bioterrorism: Recent events have created an urgent need for therapeutic strategies to treat anthrax, an infectious disease caused by the toxigenic bacterium Bacillus anthracis. A new class of aminoglycosides (see picture) are powerful inhi