23754-29-2

Basic information

• Product Name: 9-[5-methyl-2,3-O-(1-methylethylidene)pentofuranosyluronosyl]-9H-purin-6-amine
• CAS NO: 23754-29-2
• Molecular Formula: C₁₄H₁₇N₅O₅
• Molecular Weight: 335.3153
• Mol File: 23754-29-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 538.2°C at 760 mmHg
• Flash Point: 279.3°C
• Density: 1.74g/cm³
• Vapor Pressure: 1.18E-11mmHg at 25°C
• Refractive Index: 1.752
• CAS DataBase Reference: 9-[5-methyl-2,3-O-(1-methylethylidene)pentofuranosyluronosyl]-9H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[5-methyl-2,3-O-(1-methylethylidene)pentofuranosyluronosyl]-9H-purin-6-amine(23754-29-2)
• EPA Substance Registry System: 9-[5-methyl-2,3-O-(1-methylethylidene)pentofuranosyluronosyl]-9H-purin-6-amine(23754-29-2)

Safety Data

• Hazardous Substances Data: 23754-29-2(Hazardous Substances Data)

Upstream product

• 69530-93-4 5'-(O-tert-butyldimethylsilyl)adenosine 
• 19234-66-3 2',3'-isopropylideneadenosine-5'-carboxylic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 362-75-4 2',3'-isopropylidene adenosine 
• 186581-53-3 diazomethane 

Downstream Products

• 35788-27-3 5'-N-methylcarboxamidoadenosine 
• 35788-21-7 adenosine 5'-carboxamide 
• 57872-79-4 adenosine-5'-(N-benzylcarboxamide) 
• 39491-51-5 5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine 

Relevant articles and documents

Avoiding Antibiotic Inactivation in Mycobacterium tuberculosis by Rv3406 through Strategic Nucleoside Modification

5′-[N-(d-biotinoyl)sulfamoyl]amino-5′-deoxyadenosine (Bio-AMS, 1) possesses selective activity against Mycobacterium tuberculosis (Mtb) and arrests fatty acid and lipid biosynthesis through inhibition of the Mycobacterium tuberculosis biotin protein ligase (MtBPL). Mtb develops spontaneous resistance to 1 with a frequency of at least 1 × 10-7 by overexpression of Rv3406, a type II sulfatase that enzymatically inactivates 1. In an effort to circumvent this resistance mechanism, we describe herein strategic modification of the nucleoside at the 5′-position to prevent enzymatic inactivation. The new analogues retained subnanomolar potency to MtBPL (KD = 0.66-0.97 nM), and 5′R-C-methyl derivative 6 exhibited identical antimycobacterial activity toward: Mtb H37Rv, MtBPL overexpression, and an isogenic Rv3406 overexpression strain (minimum inhibitory concentration, MIC = 1.56 μM). Moreover, 6 was not metabolized by recombinant Rv3406 and resistant mutants to 6 could not be isolated (frequency of resistance -10) demonstrating it successfully overcame Rv3406-mediated resistance.

Structure-Activity Relationships of N6-Benzyladenosine-5'-uronamides as A3-Selective Adenosine Agonists

Adenosine analogues modified at the 5'-position as uronamides and/or as N6-benzyl derivatives were synthesized.These derivatives were examined for affinity in radioligand binding assays at the newly discovered rat brain A3 adenosine receptor and at rat brain A1 and A2a receptors. 5'-Uronamide substituents favored A3 selectivity in the order N-methyl > N-ethyl ca. unsubstituted carboxamide > N-cyclopropyl. 5'-(N-Methylcarboxamido)-N6-benzyladenosine was 37-56-fold more selective for A3 receptors.Potency at A3 receptors was enhanced upon substitution of the benzyl substituent with nitro and other groups. 5'-N-Methyluronamides and N6-(3-substitutedbenzyl)adenosines are optimal for potency and selectivity at A3 receptors.A series of 3-(halobenzyl)-5'-N-ethyluronamide derivatives showed the order of potency at A1 and A2a receptors of I ca.Br > Cl > F.At A3 receptors the 3-F derivative was weaker than the other halo derivatives. 5'-N-Methyl-N6-(3-iodobenzyl)adenosine displayed a Ki value of 1.1 nM at A3 receptors and selectivity versus A1 and A2a receptors of 50-fold.A series of methoxybenzyl derivatives showed that a 4-methoxy group best favored A3 selectivity.A 4-sulfobenzyl derivative was a specific ligand at A3 receptors of moderate potency.An aryl amino derivative was prepared as a probe for radioiodination and receptor cross-linking.

Conversion of 2',3'-O-isopropylidene adenosine into its 5',5'-di-C-methyl derivative.

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