37739-05-2 Usage
Description
CCPA, or 2-Chloro-N6-cyclopentyladenosine, is a selective adenosine receptor agonist with high selectivity for the A1 adenosine receptor. It is a chemical compound that plays a significant role in various applications due to its ability to modulate adenosine receptor functions.
Uses
Used in Central Nervous System (CNS) Disorders:
CCPA is used as an adenosine A1 receptor agonist for treating central nervous system (CNS) disorders. It helps in modulating the adenosine receptors, which are involved in various physiological processes in the CNS.
Used in Cardiovascular Applications:
CCPA is used as a selective adenosine receptor agonist for inhibiting angiotensin II induced cardiomyocyte hypertrophy via the calcineurin signaling pathway. This application is particularly relevant in the context of cardiovascular health and disease management.
Used in Research and Drug Development:
CCPA is often used in combination with other adenosine receptor agonists and antagonists to resolve the functions of A1, A2A, and A3 receptor subtypes. This helps researchers and pharmaceutical companies in understanding the specific roles of these receptors and developing targeted therapies for various conditions.
Chemical Properties:
CCPA is a solid chemical compound, which contributes to its stability and ease of handling in research and pharmaceutical applications.
Biological Activity
Potent and selective adenosine A 1 receptor agonist (K i values are 0.8, 2300 and 42 nM for human A 1 , A 2A and A 3 receptors respectively; EC 50 = 18800 nM for hA 2B ). Centrally active following systemic administration in vivo .
Biochem/physiol Actions
A1 adenosine receptor agonist with high selectivity: reportedly 10,000-fold for A1 over A2 receptors.
references
[1]. lohse mj, klotz kn, schwabe u, et al. 2-chloro-n6-cyclopentyladenosine: a highly selective agonist at a1 adenosine receptors. naunyn schmiedebergs arch pharmacol, 1988, 337(6): 687-689.[2]. monopoli a, conti a, dionisotti s, et al. pharmacology of the highly selective a1 adenosine receptor agonist 2-chloro-n6-cyclopentyladenosine. arzneimittelforschung, 1994, 44(12): 1305-1312.[3]. concas a, santoro g, mascia mp, et al. anticonvulsant doses of 2-chloro-n6-cyclopentyladenosine, an adenosine a1 receptor agonist, reduce gabaergic transmission in different areas of the mouse brain. j pharmacol exp ther, 1993, 267(2): 844-851.[4]. sandoli d, chiu pj, chintala m, et al. in vivo and ex vivo effects of adenosine a1 and a2 receptor agonists on platelet aggregation in the rabbit. eur j pharmacol, 1994, 259(1): 43-49.
Check Digit Verification of cas no
The CAS Registry Mumber 37739-05-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,7,7,3 and 9 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 37739-05:
(7*3)+(6*7)+(5*7)+(4*3)+(3*9)+(2*0)+(1*5)=142
142 % 10 = 2
So 37739-05-2 is a valid CAS Registry Number.
InChI:InChI=1/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
37739-05-2Relevant articles and documents
Synthesis and utility of 2-halo-O6-(benzotriazol-1-yl)- functionalized purine nucleosides
Devine, Shane M.,Scammells, Peter J.
, p. 1092 - 1098 (2011)
An efficient synthesis of 2-halo-O6-(benzotriazol-1-yl)- substituted purine nucleosides has been accomplished via (benzotriazol-1-yloxy) tris(dimethylamino)phosphonium hexafluorophosphate (BOP)-mediated coupling and subsequent halogenation via diazotization of the 2-amino group of various protected guanosines and directly from guanosine itself. These products are amenable to substitution and coupling reactions in the 2- and 6-positions and, accordingly, provide efficient access to highly functionalized purine nucleosides.
Discovery of AB680: A Potent and Selective Inhibitor of CD73
Lawson, Kenneth V.,Kalisiak, Jaroslaw,Lindsey, Erick A.,Newcomb, Eric T.,Leleti, Manmohan Reddy,Debien, Laurent,Rosen, Brandon R.,Miles, Dillon H.,Sharif, Ehesan U.,Jeffrey, Jenna L.,Tan, Joanne B. L.,Chen, Ada,Zhao, Sharon,Xu, Guifen,Fu, Lijuan,Jin, Lixia,Park, Tim W.,Berry, Wade,Moschütz, Susanne,Scaletti, Emma,Str?ter, Norbert,Walker, Nigel P.,Young, Stephen W.,Walters, Matthew J.,Schindler, Uli,Powers, Jay P.
, p. 11448 - 11468 (2020/11/26)
Extracellular adenosine (ADO), present in high concentrations in the tumor microenvironment (TME), suppresses immune function via inhibition of T cell and NK cell activation. Intratumoral generation of ADO depends on the sequential catabolism of ATP by two ecto-nucleotidases, CD39 (ATP → AMP) and CD73 (AMP → ADO). Inhibition of CD73 eliminates a major pathway of ADO production in the TME and can reverse ADO-mediated immune suppression. Extensive interrogation of structure-activity relationships (SARs), structure-based drug design, and optimization of pharmacokinetic properties culminated in the discovery of AB680, a highly potent (Ki = 5 pM), reversible, and selective inhibitor of CD73. AB680 is further characterized by very low clearance and long half-lives across preclinical species, resulting in a PK profile suitable for long-acting parenteral administration. AB680 is currently being evaluated in phase 1 clinical trials. Initial data show AB680 is well tolerated and exhibits a pharmacokinetic profile suitable for biweekly (Q2W) iv-administration in human.
INHIBITORS OF ADENOSINE 5'-NUCLEOTIDASE
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Paragraph 0211, (2018/04/21)
Compounds that modulate the conversion of AMP to adenosine by 5'- nucleotidase, ecto, and compositions containing the compounds and methods for synthesizing the compounds, are described herein. The use of such compounds and compositions for the treatment
