204512-90-3

Basic information

• Product Name: N6-[3(R)-Tetrahydrofuranyl]adenosine
• Synonyms: Tecadenoson ; CVT-510; (2R,3R,4S,5R)-2-(Hydroxymethyl)-5-[6-[tetrahydrofuran-3(R)-ylamino]-9H-purin-9-yl]tetrahydrofuran-3,4-diol; N-[(3R)-tetrahydrofuran-3-yl]adenosine
• CAS NO: 204512-90-3
• Molecular Formula: C₁₄H₁₉N₅O₅
• Molecular Weight: 337.3312
• Mol File: 204512-90-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 704.9°C at 760 mmHg
• Flash Point: 380.1°C
• Density: 1.89g/cm³
• Vapor Pressure: 7.4E-21mmHg at 25°C
• Refractive Index: 1.83
• CAS DataBase Reference: N6-[3(R)-Tetrahydrofuranyl]adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: N6-[3(R)-Tetrahydrofuranyl]adenosine(204512-90-3)
• EPA Substance Registry System: N6-[3(R)-Tetrahydrofuranyl]adenosine(204512-90-3)

Safety Data

• Hazardous Substances Data: 204512-90-3(Hazardous Substances Data)

Upstream product

• 5987-73-5 2',3',5'-O-triacetyl-6-chloroinosine 
• 2004-06-0 6-Chloropurine riboside 
• 111769-27-8 (R)-3-aminotetrahydrofuranyl tosylate 
• 309724-86-5 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furan-3-yl ester 

Relevant articles and documents

Affinity and intrinsic efficacy (IE) of 5′-carbamoyl adenosine analogues for the A1 adenosine receptor - Efforts towards the discovery of a chronic ventricular rate control agent for the treatment of atrial fibrillation (AF)

The SAR for the affinity to the A1 adenosine receptor and relative intrinsic efficacy (IE, [35S]-GTPγS binding) of a series of 5′-carbamate and 5′-thionocarbamate derivatives of tecadenoson is described. Based on this SAR, selected compounds were evaluated in guinea pig isolated hearts to determine whether they were partial or full agonists with respect to their negative dromotropism, an A1 AdoR mediated effect. Progress towards obtaining a partial A1 AdoR agonist to potentially control ventricular rate during atrial fibrillation has been made with the discovery of several potent partial A1 AdoR agonists (compounds 13, 14, and 17).

Structure-activity relationships of adenosines with heterocyclic N6-substituents

Two series of N6-substituted adenosines with monocyclic and bicyclic N6 substituents containing a heteroatom were synthesized in good yields. These derivatives were assessed for their affinity ([3H]CPX), potency, and intrinsic activity (cAMP accumulation) at the A1 adenosine receptor in DDT1 MF-2 cells. In the monocyclic series, the N6-tetrahydrofuran-3-yl and thiolan-3-yl adenosines (1 and 26, respectively) were found to possess similar activities, whereas the corresponding selenium analogue 27 was found to be more potent. A series of nitrogen containing analogues showed varying properties, N6-((3R)-1-benzyloxycarbonylpyrrolidin-3-yl)adenosine (30) was the most potent at the A1AR; IC50 = 3.2 nM. In the bicyclic series, the effect of a 7-azabicyclo[2.2.1]heptan-2-yl substituent in the N6-position was explored. N6-(7-Azabicyclo[2.2.1]heptan-2-yl)adenosine (38) proved to be a reasonably potent A1 agonist (Ki = 51 nM, IC50 = 35 nM) while further substitution on the 7″-nitrogen with tert-butoxycarbonyl (31, IC50 = 2.5 nM) and 2-bromobenzyloxycarbonyl (34, IC50 = 9.0 nM) gave highly potent A1AR agonists.