34245-49-3

Basic information

• Product Name: Adenosine, 5'-deoxy-5'-(MethylaMino)-2',3'-O-(1-Methylethylidene)-
• Synonyms: 9-((3aR,4R,6R,6aR)-2,2-DiMethyl-6-((MethylaMino)Methyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-aMine;9-((3AR,4R,6R,6aR)-2,2-Dimethyl-6-((methylamino)methyl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl);Adenosine, 5'-deoxy-5'-(MethylaMino)-2',3'-O-(1-Methylethylidene)-;9-((3AR,4R,6R,6aR)-2,2-Dimethyl-6-((methylamino)methyl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H;Adenosine,51-deoxy-51-(methylamino)-21,31-O-(1-methylethylidene)-
• CAS NO: 34245-49-3
• Molecular Formula: C₁₄H₂₀N₆O₃
• Molecular Weight: 320.347
• Mol File: 34245-49-3.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Adenosine, 5'-deoxy-5'-(MethylaMino)-2',3'-O-(1-Methylethylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine, 5'-deoxy-5'-(MethylaMino)-2',3'-O-(1-Methylethylidene)-(34245-49-3)
• EPA Substance Registry System: Adenosine, 5'-deoxy-5'-(MethylaMino)-2',3'-O-(1-Methylethylidene)-(34245-49-3)

Safety Data

• Hazardous Substances Data: 34245-49-3(Hazardous Substances Data)

Usage

General Description

Adenosine, 5'-deoxy-5'-(methylamino)-2',3'-O-(1-methylethylidene)- is a modified form of adenosine, a naturally occurring nucleoside. This chemical compound has a methylamino group attached to the 5' carbon of the ribose ring and an isopropylidene group attached to the 2' and 3' carbons. It is commonly used as a pharmaceutical agent to treat certain heart rhythm disorders, including paroxysmal supraventricular tachycardia. Adenosine, 5'-deoxy-5'-(methylamino)-2',3'-O-(1-methylethylidene)- works by slowing down the electrical conduction in the heart, which can help restore a normal heart rhythm. It is also being researched for its potential anti-inflammatory and neuroprotective properties.

Upstream product

• 5605-63-0 ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate 
• 74-89-5 methylamine 
• 24514-56-5 9-((3aR,4R,6S,6aS)-6-(chloromethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine 
• 362-75-4 2',3'-isopropylidene adenosine 
• 68179-90-8 ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl methanesulfonate 
• 1194995-79-3 5'-deoxy-5'-N-methyl-N-o-nitrobenzenesulfonylamino-2',3'-O,O-(1-methylethylidene)adenosine 

Downstream Products

• 176847-64-6 (4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one 
• 478161-08-9 4-({[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-methyl-amino}-methyl)-benzonitrile 
• 478161-09-0 2-({[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-methyl-amino}-methyl)-benzonitrile 
• 478161-10-3 9-((3aR,4R,6R,6aR)-6-{[(4-Aminomethyl-benzyl)-methyl-amino]-methyl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-ylamine 
• 478161-11-4 9-((3aR,4R,6R,6aR)-6-{[(2-Aminomethyl-benzyl)-methyl-amino]-methyl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-ylamine 
• 111770-79-7 5'-[N-[(3S)-3-amino-3-carboxypropyl]-N-methylamino]-5'-deoxyadenosine 
• 129828-73-5 N⁴-(5'-adenosyl)-N⁴-methyl-2-(R,S),4-diaminobutanoic acid 
• 1129995-73-8 5'-deoxy-5'-N-methyl-N-[4-{(S)-2-(N-tert-butoxycarbonyl)amino-butyric acid}] benzyl ester-2',3'-O,O-(1-methylethylidene)adenosine 
• 1380350-54-8 benzyl (3-((((3aR,4R,6R,6aR)-6-(6-amino-911-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)carbamate 
• 1381760-79-7 C₂₄H₃₁N₇O₅ 
• 1381762-10-2 benzyl(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)propyl)carbamate 
• 1381761-10-9 C₂₅H₃₂N₆O₅ 
• 1381760-99-1 C₂₅H₃₃N₇O₅ 
• 134848-96-7 benzyl 5-hydroxy pentanoate 

Relevant articles and documents

Synthesis and evaluation of analogs of 5′-(((Z)-4-amino-2-butenyl)methylamino)-5′-deoxyadenosine (MDL 73811, or AbeAdo) – An inhibitor of S-adenosylmethionine decarboxylase with antitrypanosomal activity

We describe our efforts to improve the pharmacokinetic properties of a mechanism-based suicide inhibitor of the polyamine biosynthetic enzyme S-adenosylmethionine decarboxylase (AdoMetDC), essential for the survival of the eukaryotic parasite Trypanosoma brucei responsible for Human African Trypanosomiasis (HAT). The lead compound, 5′-(((Z)-4-amino-2-butenyl)methylamino)-5′-deoxyadenosine (1, also known as MDL 73811, or AbeAdo), has curative efficacy at a low dosage in a hemolymphatic model of HAT but displayed no demonstrable effect in a mouse model of the CNS stage of HAT due to poor blood–brain barrier permeation. Therefore, we prepared and evaluated an extensive set of analogs with modifications in the aminobutenyl side chain, the 5′-amine, the ribose, and the purine fragments. Although we gained valuable structure–activity insights from this comprehensive dataset, we did not gain traction on improving the prospects for CNS penetration while retaining the potent antiparasitic activity and metabolic stability of the lead compound 1.

An acyl-SAM analog as an affinity ligand for identifying quorum sensing signal synthases

N-Acylhomoserine lactones (AHLs) are quorum sensing signals produced by Gram-negative bacteria. We here report the affinity purification of AHL synthases using beads conjugated with an enzyme inhibitor, which was designed based on the catalytic intermediate acyl-SAM. the Partner Organisations 2014.

Identification of stable S-adenosylmethionine (SAM) analogues derivatised with bioorthogonal tags: Effect of ligands on the affinity of the E. coli methionine repressor, MetJ, for its operator DNA

The efficient synthesis of a range of stable SAM mimetics, and their ability to promote the binding of the E. coli methionine repressor (MetJ) to its operator DNA, is described.