204512-90-3,MFCD08690887
Catalog No.:AA01EOLR

204512-90-3 | Tecadenoson

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Purity
Availability
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100mg
≥95%
in stock  
$116.00   $81.00
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250mg
≥95%
in stock  
$269.00   $188.00
- +
500mg
≥95%
in stock  
$480.00   $336.00
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1g
≥95%
in stock  
$790.00   $553.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA01EOLR
Chemical Name:
Tecadenoson
CAS Number:
204512-90-3
Molecular Formula:
C14H19N5O5
Molecular Weight:
337.3312
MDL Number:
MFCD08690887
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N[C@H]1COCC1
Properties
Computed Properties
 
Complexity:
446  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0  
Rotatable Bond Count:
4  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
-0.3  

Downstream Synthesis Route

[1]Palle,VenkataP.;Varkhedkar,Vaibhav;Ibrahim,Prabha;Ahmed,Hiba;Li,Zhihe;Gao,Zhenhai;Ozeck,Mark;Wu,Yuzhi;Zeng,Dewan;Wu,Lin;Leung,Kwan;Chu,Nancy;Zablocki,JeffA.[BioorganicandMedicinalChemistryLetters,2004,vol.14,#2,p.535-539]

[2]Morrison,ChristopherF.;Elzein,Elfatih;Jiang,Bob;Ibrahim,PrabhaN.;Marquart,Timothy;Palle,Venkata;Shenk,KevinD.;Varkhedkar,Vaibhav;Maa,Tenning;Wu,Lin;Wu,Yuzhi;Zeng,Dewan;Fong,Irving;Lustig,David;Leung,Kwan;Zablocki,JeffA.[BioorganicandMedicinalChemistryLetters,2004,vol.14,#14,p.3793-3797]

[3]Petrelli,Riccardo;Scortichini,Mirko;Belardo,Carmela;Boccella,Serena;Luongo,Livio;Capone,Fabio;Kachler,Sonja;Vita,Patrizia;DelBello,Fabio;Maione,Sabatino;Lavecchia,Antonio;Klotz,Karl-Norbert;Cappellacci,Loredana[JournalofMedicinalChemistry,2018,vol.61,#1,p.305-318]

[1]Palle,VenkataP.;Varkhedkar,Vaibhav;Ibrahim,Prabha;Ahmed,Hiba;Li,Zhihe;Gao,Zhenhai;Ozeck,Mark;Wu,Yuzhi;Zeng,Dewan;Wu,Lin;Leung,Kwan;Chu,Nancy;Zablocki,JeffA.[BioorganicandMedicinalChemistryLetters,2004,vol.14,#2,p.535-539]

[2]Petrelli,Riccardo;Scortichini,Mirko;Belardo,Carmela;Boccella,Serena;Luongo,Livio;Capone,Fabio;Kachler,Sonja;Vita,Patrizia;DelBello,Fabio;Maione,Sabatino;Lavecchia,Antonio;Klotz,Karl-Norbert;Cappellacci,Loredana[JournalofMedicinalChemistry,2018,vol.61,#1,p.305-318]

[1]BioorganicandMedicinalChemistryLetters,2007,vol.17,p.6779-6784

204512-90-3   
(2R,3R,4S,5S)-2-{6-(R)-(Tetrahydro-furan-3-yl)amino-purin-9-yl}-5-(thiazol-2-ylsulfanylmethyl)-tetrahydro-furan-3,4-diol 

[1]Morrison,ChristopherF.;Elzein,Elfatih;Jiang,Bob;Ibrahim,PrabhaN.;Marquart,Timothy;Palle,Venkata;Shenk,KevinD.;Varkhedkar,Vaibhav;Maa,Tenning;Wu,Lin;Wu,Yuzhi;Zeng,Dewan;Fong,Irving;Lustig,David;Leung,Kwan;Zablocki,JeffA.[BioorganicandMedicinalChemistryLetters,2004,vol.14,#14,p.3793-3797]

204512-90-3   
(2S,3S,4R,5R)-2-(Pyridin-2-ylsulfanylmethyl)-5-{6-(R)-(tetrahydro-furan-3-yl)amino-purin-9-yl}-tetrahydro-furan-3,4-diol 

[1]Morrison,ChristopherF.;Elzein,Elfatih;Jiang,Bob;Ibrahim,PrabhaN.;Marquart,Timothy;Palle,Venkata;Shenk,KevinD.;Varkhedkar,Vaibhav;Maa,Tenning;Wu,Lin;Wu,Yuzhi;Zeng,Dewan;Fong,Irving;Lustig,David;Leung,Kwan;Zablocki,JeffA.[BioorganicandMedicinalChemistryLetters,2004,vol.14,#14,p.3793-3797]

Literature

Title: Recent developments in adenosine receptor ligands and their potential as novel drugs.

Journal: Biochimica et biophysica acta 20110501

Title: 5'-Carbamoyl derivatives of 2'-C-methyl-purine nucleosides as selective A1 adenosine receptor agonists: affinity, efficacy, and selectivity for A1 receptor from different species.

Journal: Bioorganic & medicinal chemistry 20080101

Title: Structure-activity relationships of adenosines with heterocyclic N6-substituents.

Journal: Bioorganic & medicinal chemistry letters 20071215

Title: New antiarrhythmic treatment of atrial fibrillation.

Journal: Expert review of cardiovascular therapy 20070701

Title: Adenosine receptors as therapeutic targets.

Journal: Nature reviews. Drug discovery 20060301

Title: Trial to evaluate the management of paroxysmal supraventricular tachycardia during an electrophysiology study with tecadenoson.

Journal: Circulation 20050621

Title: Tecadenoson: a novel, selective A1 adenosine receptor agonist.

Journal: Cardiology in review 20050101

Title: Structure-affinity relationships of 5'-aromatic ethers and 5'-aromatic sulfides as partial A1 adenosine agonists, potential supraventricular anti-arrhythmic agents.

Journal: Bioorganic & medicinal chemistry letters 20040716

Title: 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).

Journal: Bioorganic & medicinal chemistry letters 20040119

Title: Termination of paroxysmal supraventricular tachycardia by tecadenoson (CVT-510), a novel A1-adenosine receptor agonist.

Journal: Journal of the American College of Cardiology 20030917

Title: N-[3-(R)-tetrahydrofuranyl]-6-aminopurine riboside, an A1 adenosine receptor agonist, antagonizes catecholamine-induced lipolysis without cardiovascular effects in awake rats.

Journal: The Journal of pharmacology and experimental therapeutics 20030401

Title: CVT-510: a selective A1 adenosine receptor agonist.

Journal: Cardiovascular drug reviews 20030101

Title: CVT-510 (CV Therapeutics).

Journal: Current opinion in investigational drugs (London, England : 2000) 20020101

Title: Electrophysiologic effects of a novel selective adenosine A1 agonist (CVT-510) on atrioventricular nodal conduction in humans.

Journal: Journal of cardiovascular pharmacology and therapeutics 20010701

Title: Snowdy S, et al. A comparison of an A1 adenosine receptor agonist (CVT-510) with diltiazem for slowing of AVnodal conduction in guinea-pig. Br J Pharmacol. 1999 Jan;126(1):137-46.

Title: Fraser H, et al. N--(R)-tetrahydrofuranyl-6-aminopurine riboside, an A1 adenosine receptor agonist, antagonizes catecholamine-induced lipolysis without cardiovascular effects in awake rats. J Pharmacol Exp Ther. 2003 Apr;305(1):225-31.

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SDS
Tags:204512-90-3 Molecular Formula|204512-90-3 MDL|204512-90-3 SMILES|204512-90-3 Tecadenoson
Catalog No.: AA01EOLR
204512-90-3,MFCD08690887
204512-90-3 | Tecadenoson
Pack Size: 100mg
Purity: ≥95%
in stock
$116.00 $81.00
Pack Size: 250mg
Purity: ≥95%
in stock
$269.00 $188.00
Pack Size: 500mg
Purity: ≥95%
in stock
$480.00 $336.00
Pack Size: 1g
Purity: ≥95%
in stock
$790.00 $553.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA01EOLR
Chemical Name: Tecadenoson
CAS Number: 204512-90-3
Molecular Formula: C14H19N5O5
Molecular Weight: 337.3312
MDL Number: MFCD08690887
SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N[C@H]1COCC1
Properties
Complexity: 446  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 5  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 24  
Hydrogen Bond Acceptor Count: 9  
Hydrogen Bond Donor Count: 4  
Isotope Atom Count: 0  
Rotatable Bond Count: 4  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: -0.3  
Downstream Synthesis Route
77-76-9    204512-90-3    309725-38-0 

[1]Palle,VenkataP.;Varkhedkar,Vaibhav;Ibrahim,Prabha;Ahmed,Hiba;Li,Zhihe;Gao,Zhenhai;Ozeck,Mark;Wu,Yuzhi;Zeng,Dewan;Wu,Lin;Leung,Kwan;Chu,Nancy;Zablocki,JeffA.[BioorganicandMedicinalChemistryLetters,2004,vol.14,#2,p.535-539]

[2]Morrison,ChristopherF.;Elzein,Elfatih;Jiang,Bob;Ibrahim,PrabhaN.;Marquart,Timothy;Palle,Venkata;Shenk,KevinD.;Varkhedkar,Vaibhav;Maa,Tenning;Wu,Lin;Wu,Yuzhi;Zeng,Dewan;Fong,Irving;Lustig,David;Leung,Kwan;Zablocki,JeffA.[BioorganicandMedicinalChemistryLetters,2004,vol.14,#14,p.3793-3797]

[3]Petrelli,Riccardo;Scortichini,Mirko;Belardo,Carmela;Boccella,Serena;Luongo,Livio;Capone,Fabio;Kachler,Sonja;Vita,Patrizia;DelBello,Fabio;Maione,Sabatino;Lavecchia,Antonio;Klotz,Karl-Norbert;Cappellacci,Loredana[JournalofMedicinalChemistry,2018,vol.61,#1,p.305-318]

309724-86-5    204512-90-3 

[1]Palle,VenkataP.;Varkhedkar,Vaibhav;Ibrahim,Prabha;Ahmed,Hiba;Li,Zhihe;Gao,Zhenhai;Ozeck,Mark;Wu,Yuzhi;Zeng,Dewan;Wu,Lin;Leung,Kwan;Chu,Nancy;Zablocki,JeffA.[BioorganicandMedicinalChemistryLetters,2004,vol.14,#2,p.535-539]

[2]Petrelli,Riccardo;Scortichini,Mirko;Belardo,Carmela;Boccella,Serena;Luongo,Livio;Capone,Fabio;Kachler,Sonja;Vita,Patrizia;DelBello,Fabio;Maione,Sabatino;Lavecchia,Antonio;Klotz,Karl-Norbert;Cappellacci,Loredana[JournalofMedicinalChemistry,2018,vol.61,#1,p.305-318]

2004-06-0    111769-27-8    204512-90-3 

[1]BioorganicandMedicinalChemistryLetters,2007,vol.17,p.6779-6784

204512-90-3   
(2R,3R,4S,5S)-2-{6-(R)-(Tetrahydro-furan-3-yl)amino-purin-9-yl}-5-(thiazol-2-ylsulfanylmethyl)-tetrahydro-furan-3,4-diol 

[1]Morrison,ChristopherF.;Elzein,Elfatih;Jiang,Bob;Ibrahim,PrabhaN.;Marquart,Timothy;Palle,Venkata;Shenk,KevinD.;Varkhedkar,Vaibhav;Maa,Tenning;Wu,Lin;Wu,Yuzhi;Zeng,Dewan;Fong,Irving;Lustig,David;Leung,Kwan;Zablocki,JeffA.[BioorganicandMedicinalChemistryLetters,2004,vol.14,#14,p.3793-3797]

204512-90-3   
(2S,3S,4R,5R)-2-(Pyridin-2-ylsulfanylmethyl)-5-{6-(R)-(tetrahydro-furan-3-yl)amino-purin-9-yl}-tetrahydro-furan-3,4-diol 

[1]Morrison,ChristopherF.;Elzein,Elfatih;Jiang,Bob;Ibrahim,PrabhaN.;Marquart,Timothy;Palle,Venkata;Shenk,KevinD.;Varkhedkar,Vaibhav;Maa,Tenning;Wu,Lin;Wu,Yuzhi;Zeng,Dewan;Fong,Irving;Lustig,David;Leung,Kwan;Zablocki,JeffA.[BioorganicandMedicinalChemistryLetters,2004,vol.14,#14,p.3793-3797]

Literature fold

Title: Recent developments in adenosine receptor ligands and their potential as novel drugs.

Journal: Biochimica et biophysica acta20110501

Title: 5'-Carbamoyl derivatives of 2'-C-methyl-purine nucleosides as selective A1 adenosine receptor agonists: affinity, efficacy, and selectivity for A1 receptor from different species.

Journal: Bioorganic & medicinal chemistry20080101

Title: Structure-activity relationships of adenosines with heterocyclic N6-substituents.

Journal: Bioorganic & medicinal chemistry letters20071215

Title: New antiarrhythmic treatment of atrial fibrillation.

Journal: Expert review of cardiovascular therapy20070701

Title: Adenosine receptors as therapeutic targets.

Journal: Nature reviews. Drug discovery20060301

Title: Trial to evaluate the management of paroxysmal supraventricular tachycardia during an electrophysiology study with tecadenoson.

Journal: Circulation20050621

Title: Tecadenoson: a novel, selective A1 adenosine receptor agonist.

Journal: Cardiology in review20050101

Title: Structure-affinity relationships of 5'-aromatic ethers and 5'-aromatic sulfides as partial A1 adenosine agonists, potential supraventricular anti-arrhythmic agents.

Journal: Bioorganic & medicinal chemistry letters20040716

Title: 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).

Journal: Bioorganic & medicinal chemistry letters20040119

Title: Termination of paroxysmal supraventricular tachycardia by tecadenoson (CVT-510), a novel A1-adenosine receptor agonist.

Journal: Journal of the American College of Cardiology20030917

Title: N-[3-(R)-tetrahydrofuranyl]-6-aminopurine riboside, an A1 adenosine receptor agonist, antagonizes catecholamine-induced lipolysis without cardiovascular effects in awake rats.

Journal: The Journal of pharmacology and experimental therapeutics20030401

Title: CVT-510: a selective A1 adenosine receptor agonist.

Journal: Cardiovascular drug reviews20030101

Title: CVT-510 (CV Therapeutics).

Journal: Current opinion in investigational drugs (London, England : 2000)20020101

Title: Electrophysiologic effects of a novel selective adenosine A1 agonist (CVT-510) on atrioventricular nodal conduction in humans.

Journal: Journal of cardiovascular pharmacology and therapeutics20010701

Title: Snowdy S, et al. A comparison of an A1 adenosine receptor agonist (CVT-510) with diltiazem for slowing of AVnodal conduction in guinea-pig. Br J Pharmacol. 1999 Jan;126(1):137-46.

Title: Fraser H, et al. N--(R)-tetrahydrofuranyl-6-aminopurine riboside, an A1 adenosine receptor agonist, antagonizes catecholamine-induced lipolysis without cardiovascular effects in awake rats. J Pharmacol Exp Ther. 2003 Apr;305(1):225-31.

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