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Merck

C7938

2-Chloro-N6-cyclopentyladenosine

adenosine receptor agonist

Synonyme(s) :

CCPA

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A propos de cet article

Formule empirique (notation de Hill) :
C15H20ClN5O4
Numéro CAS:
37739-05-2
Poids moléculaire :
369.80
NACRES:
NA.51
PubChem Substance ID:
24892583
UNSPSC Code:
41106305
MDL number:
MFCD00078574
Assay:
≥98% (TLC)
Form:
powder
Solubility:
methanol: 19.60-20.40 mg/mL, clear, colorless to faintly yellow
Storage temp.:
2-8°C

Principaux documents

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InChI

1S/C15H20ClN5O4/c16-15-19-12(18-7-3-1-2-4-7)9-13(20-15)21(6-17-9)14-11(24)10(23)8(5-22)25-14/h6-8,10-11,14,22-24H,1-5H2,(H,18,19,20)/t8-,10-,11-,14-/m1/s1

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NC4CCCC4)nc(Cl)nc23

InChI key

XSMYYYQVWPZWIZ-IDTAVKCVSA-N

assay

≥98% (TLC)

form

powder

solubility

methanol: 19.60-20.40 mg/mL, clear, colorless to faintly yellow

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Application

2-Chloro-N6-cyclopentyladenosine (CCPA) may be used as an A1 adenosine receptor agonist with high selectivity. CCPA is often used with other adenosine receptor agonists and antagonist to resolve A(1), A(2A) and A(3) receptor functions. These include DPCPX (A(1) receptor antagonist), 4-(2-[7-amino-2-(2-furyl)[1,2,4]triazolo[2,3-α][1,3,5]triazin-5-ylamino]ethyl)phenol (A(2A) receptor antagonist), and 4-[2-[[6-amino-9-(N-ethyl-β-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid hydrochloride (A(2A) receptor agonist), and Cl-IB-MECA, (A(3)) receptor agonist).

Biochem/physiol Actions

A1 adenosine receptor agonist with high selectivity: reportedly 10,000-fold for A1 over A2 receptors.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000376284
0000126946
0000376284
0000126946
0000130728

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Consulter la Bibliothèque de documents

Romeo Romagnoli et al.
Journal of medicinal chemistry, 51(18), 5875-5879 (2008-08-30)
The synthesis and evaluation of a series of 2-amino-3-(4-chlorobenzoyl)-4-[4-(alkyl/aryl)piperazin-yl]thiophene derivatives as allosteric enhancers of the A 1-adenosine receptor are described. The nature of substituents on the phenyl ring tethered to the piperazine seem to exert a fundamental influence on the
Iftikhar Ahmad et al.
Scientific reports, 10(1), 364-364 (2020-01-17)
Real world complex networks are indirect representation of complex systems. They grow over time. These networks are fragmented and raucous in practice. An important concern about complex network is link prediction. Link prediction aims to determine the possibility of probable
N L D Smith et al.
Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases, 20(8), O480-O488 (2013-11-28)
Chronic cavitary pulmonary aspergillosis (CCPA) is a progressive lung condition with a 10-30% annual mortality. Although overtly immunocompetent, some immunogenetic defect in patients is likely. To investigate a possible immunogenetic defect in CCPA, we analysed biologically plausible candidate genes in
Luca Soattin et al.
Frontiers in physiology, 11, 493-493 (2020-07-01)
Adenosine leads to atrial action potential (AP) shortening through activation of adenosine 1 receptors (A1-R) and subsequent opening of G-protein-coupled inwardly rectifying K+ channels. Extracellular production of adenosine is drastically increased during stress and ischemia. The aim of this study
Mary Clare Luca et al.
Clinical hemorheology and microcirculation, 49(1-4), 287-293 (2012-01-05)
Despite decades of research and thousands of experimental publications, acute preconditioning strategies have yet to be implemented in clinical practice. While some have attributed this to a failure of the experimental studies to mimic the clinical environment, others have suggested
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