868273-06-7 Usage
Uses
Used in Pharmaceutical Research:
Org 27569 is used as a research compound for investigating the structure-activity relationships of indole-carboxamides as CB1 receptor allosteric modulators. Its unique chemical structure allows scientists to explore the interactions between these compounds and the CB1 receptor, providing insights into the development of novel therapeutic agents targeting the endocannabinoid system.
Used in Drug Discovery:
As a selective CB1 receptor allosteric modulator, Org 27569 is employed in drug discovery efforts aimed at identifying new treatments for various disorders associated with the endocannabinoid system. These may include neurological, psychiatric, and metabolic conditions, as well as pain management and addiction therapy.
Used in Biological Studies:
Org 27569 is utilized in biological studies to understand the role of the CB1 receptor in various physiological processes and disease states. By modulating the activity of the CB1 receptor, researchers can gain a better understanding of its potential as a therapeutic target and the mechanisms by which it influences cellular and organismal functions.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic efficacy of Org 27569, researchers are developing novel drug delivery systems. These systems may include nanoparticles, liposomes, or other carriers that can improve the compound's solubility, stability, and targeted delivery to specific tissues or cells.
Biological Activity
Potent CB 1 receptor allosteric modulator (pEC 50 = 8.24). Significantly increases binding of the CB 1 agonist [ 3 H]CP 55.940 (pK b = 5.67) and decreases binding of the CB 1 inverse agonist [ 3 H]SR 141716A (pK b = 5.95). Inhibits CB 1 receptor antagonist efficacy in vitro (pK b = 7.57).
references
[1] price mr1, baillie gl, thomas a, stevenson la, easson m, goodwin r, mclean a, mcintosh l, goodwin g, walker g, westwood p, marrs j, thomson f, cowley p, christopoulos a, pertwee rg, ross ra. allosteric modulation of the cannabinoid cb1 receptor. mol pharmacol. 2005 nov;68(5):1484-95. epub 2005 aug 19.[2] fay jf1, farrens dl. a key agonist-induced conformational change in the cannabinoid receptor cb1 is blocked by the allosteric ligand org 27569. j biol chem. 2012 sep 28;287(40):33873-82. epub 2012 jul 30.
Check Digit Verification of cas no
The CAS Registry Mumber 868273-06-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,6,8,2,7 and 3 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 868273-06:
(8*8)+(7*6)+(6*8)+(5*2)+(4*7)+(3*3)+(2*0)+(1*6)=207
207 % 10 = 7
So 868273-06-7 is a valid CAS Registry Number.
InChI:InChI=1/C24H28ClN3O/c1-2-20-21-16-18(25)8-11-22(21)27-23(20)24(29)26-13-12-17-6-9-19(10-7-17)28-14-4-3-5-15-28/h6-11,16,27H,2-5,12-15H2,1H3,(H,26,29)
868273-06-7Relevant academic research and scientific papers
Novel Electrophilic and Photoaffinity Covalent Probes for Mapping the Cannabinoid 1 Receptor Allosteric Site(s)
Kulkarni, Pushkar M.,Kulkarni, Abhijit R.,Korde, Anisha,Tichkule, Ritesh B.,Laprairie, Robert B.,Denovan-Wright, Eileen M.,Zhou, Han,Janero, David R.,Zvonok, Nikolai,Makriyannis, Alexandros,Cascio, Maria G.,Pertwee, Roger G.,Thakur, Ganesh A.
, p. 44 - 60 (2016/01/29)
Undesirable side effects associated with orthosteric agonists/antagonists of cannabinoid 1 receptor (CB1R), a tractable target for treating several pathologies affecting humans, have greatly limited their translational potential. Recent discovery of CB1R negative allosteric modulators (NAMs) has renewed interest in CB1R by offering a potentially safer therapeutic avenue. To elucidate the CB1R allosteric binding motif and thereby facilitate rational drug discovery, we report the synthesis and biochemical characterization of first covalent ligands designed to bind irreversibly to the CB1R allosteric site. Either an electrophilic or a photoactivatable group was introduced at key positions of two classical CB1R NAMs: Org27569 (1) and PSNCBAM-1 (2). Among these, 20 (GAT100) emerged as the most potent NAM in functional assays, did not exhibit inverse agonism, and behaved as a robust positive allosteric modulator of binding of orthosteric agonist CP55,940. This novel covalent probe can serve as a useful tool for characterizing CB1R allosteric ligand-binding motifs.
Indole-2-carboxamides as allosteric modulators of the cannabinoid CB 1 receptor
Piscitelli, Francesco,Ligresti, Alessia,La Regina, Giuseppe,Coluccia, Antonio,Morera, Ludovica,Allarà, Marco,Novellino, Ettore,Di Marzo, Vincenzo,Silvestri, Romano
, p. 5627 - 5631 (2012/08/28)
We synthesized new N-phenylethyl-1H-indole-2-carboxamides as the first SAR study of allosteric modulators of the CB1 receptor. The presence of the carboxamide functionality was required in order to obtain a stimulatory effect. The maximum stimulatory activity on CB1 was exerted by carboxamides 13 (EC50 = 50 nM) and 21 (EC50 = 90 nM) bearing a dimethylamino or piperidinyl group, respectively, at position 4 of the phenethyl moiety and a chlorine atom at position 5 of the indole.
