23707-33-7

Basic information

• Product Name: METRIFUDIL
• Synonyms: METRIFUDIL;6-(2-Methylbenzylamino)-9-β-D-ribofuranosyl-9H-purine;N-(2-Methylbenzyl)adenosine;Th-322;Adenosine, N-[(2-Methylphenyl)Methyl]-;(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[(2-methylphenyl)methylamino]purin-9-yl]oxolane-3,4-diol
• CAS NO: 23707-33-7
• Molecular Formula: C₁₈H₂₁N₅O₄
• Molecular Weight: 371.395
• Mol File: 23707-33-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 694.1°C at 760 mmHg
• Flash Point: 373.6°C
• Appearance: /
• Density: 1.57g/cm³
• Vapor Pressure: 3.15E-20mmHg at 25°C
• Refractive Index: 1.743
• Storage Temp.: −20°C
• Solubility: H2O: 0.3 mg/mL
• CAS DataBase Reference: METRIFUDIL(CAS DataBase Reference)
• NIST Chemistry Reference: METRIFUDIL(23707-33-7)
• EPA Substance Registry System: METRIFUDIL(23707-33-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 23707-33-7(Hazardous Substances Data)

Usage

Uses

Metrifudil is a N6-substituted adenosine derivative that is potent and selective A3 adenosine receptor agonist.

InChI:InChI=1/C18H21N5O4/c1-10-4-2-3-5-11(10)6-19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)12(7-24)27-18/h2-5,8-9,12,14-15,18,24-26H,6-7H2,1H3,(H,19,20,21)/t12-,14-,15-,18-/m1/s1

Upstream product

• 89-93-0 ortho-methylbenzylamine 
• 2004-06-0 6-Chloropurine riboside 

Relevant articles and documents

Preparation, biological activity and endogenous occurrence of N6-benzyladenosines

Cytokinin activity of forty-eight 6-benzyladenosine derivatives at both the receptor and cellular levels as well as their anticancer properties were compared in various in vitro assays. The compounds were prepared by the condensation of 6-chloropurine rib

Anti-HCV nucleoside derivatives

The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

N-substituted adenosines as novel neuroprotective A1 agonists with diminished hypotensive effects

The synthesis and pharmacological profile of a series of neuroprotective adenosine agonists are described. Novel A1 agonists with potent central nervous system effects and diminished influence on the cardiovascular system are reported and compared to selected reference adenosine-agonists. The novel compounds featured are derived structurally from two key lead structures: 2- chloro-N-(1-phenoxy-2-propyl)adenosine (NNC 21-0041, 9) and 2-chloro-N-(1- piperidinyl)adenosine (NNC 90-1515, 4). The agonists are characterized in terms of their in vitro profiles, both binding and functional, and in vivo activity in relevant animal models. Neuroprotective properties assessed after postischemic dosing in a Mongolian gerbil severe temporary forebrain ischemia paradigm, using hippocampal CA1 damage endpoints, and the efficacy of these agonists in an A1 functional assay show similarities to some reference adenosine agonists. However, the new compounds we describe exhibit diminished cardiovascular effects in both anesthetized and awake rats when compared to reference A1 agonists such as (R)phenylisopropyladenosine (R-PIA, 5), N- cyclopentyladenosine (CPA, 2), 4, N-[(1S,trans)-2- hydroxycyclopentyl]adenosine (GR 79236, 26), N-cyclohexyl-2'-O- methyladenosine (SDZ WAG 994, 27), and N-[(2-methylphenyl)methyl]adenosine (Metrifudil, 28). In mouse permanent middle cerebral artery occlusion focal ischemia, 2-chloro-N-[(R)-[(2-benzothiazolyl)thio]-2-propyl]adenosine (NNC 21-0136, 12) exhibited significant neuroprotection at the remarkably low total intraperitoneal dose of 0.1 mg/kg, a dose at which no cardiovascular effects are observed in conscious rats. The novel agonists described inhibit 6,7-dimethoxy-4-ethyl-β-carboline-3-carboxylate-induced seizures, and in mouse locomotor activity higher doses are required to reach ED50 values than for reference A1 agonists. We conclude that two of the novel adenosine derivatives revealed herein, 12 and 5'-deoxy-5'-chloro-N-[4-(phenylthio)-1- piperidinyl]adenosine (NNC 21-0147, 13), representatives of a new series of P1 ligands, reinforce the fact that novel selective adenosine A1 agonists have potential in the treatment of cerebral ischemia in humans.