SB269652Dopamine D2 receptor modulator CAS# 215802-15-6 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 215802-15-6 | SDF | Download SDF |
PubChem ID | 9910352 | Appearance | Powder |
Formula | C27H30N4O | M.Wt | 426.55 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | Soluble in DMSO | ||
Chemical Name | N-[4-[2-(7-cyano-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]cyclohexyl]-1H-indole-2-carboxamide | ||
SMILES | C1CC(CCC1CCN2CCC3=C(C2)C=C(C=C3)C#N)NC(=O)C4=CC5=CC=CC=C5N4 | ||
Standard InChIKey | JGLGOAQPUQITLD-UHFFFAOYSA-N | ||
Standard InChI | InChI=1S/C27H30N4O/c28-17-20-5-8-21-12-14-31(18-23(21)15-20)13-11-19-6-9-24(10-7-19)29-27(32)26-16-22-3-1-2-4-25(22)30-26/h1-5,8,15-16,19,24,30H,6-7,9-14,18H2,(H,29,32) | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
SB269652 Dilution Calculator
SB269652 Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 2.3444 mL | 11.722 mL | 23.4439 mL | 46.8878 mL | 58.6098 mL |
5 mM | 0.4689 mL | 2.3444 mL | 4.6888 mL | 9.3776 mL | 11.722 mL |
10 mM | 0.2344 mL | 1.1722 mL | 2.3444 mL | 4.6888 mL | 5.861 mL |
50 mM | 0.0469 mL | 0.2344 mL | 0.4689 mL | 0.9378 mL | 1.1722 mL |
100 mM | 0.0234 mL | 0.1172 mL | 0.2344 mL | 0.4689 mL | 0.5861 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
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SB269652 is the first drug-like allosteric modulator of the dopamine D2 receptor (D2R); a new chemical probe that can differentiate D2R monomers from dimers or oligomers depending on the observed pharmacology.
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The First Negative Allosteric Modulator for Dopamine D2 and D3 Receptors, SB269652 May Lead to a New Generation of Antipsychotic Drugs.[Pubmed:28265019]
Mol Pharmacol. 2017 Jun;91(6):586-594.
D2 and D3 dopamine receptors belong to the largest family of cell surface proteins in eukaryotes, the G protein-coupled receptors (GPCRs). Considering their crucial physiologic functions and their relatively accessible cellular locations, GPCRs represent one of the most important classes of therapeutic targets. Until recently, the only strategy to develop drugs regulating GPCR activity was through the identification of compounds that directly acted on the orthosteric sites for endogenous ligands. However, many efforts have recently been made to identify small molecules that are able to interact with allosteric sites. These sites are less well-conserved, therefore allosteric ligands have greater selectivity on the specific receptor. Strikingly, the use of allosteric modulators can provide specific advantages, such as an increased selectivity for GPCR subunits and the ability to introduce specific beneficial therapeutic effects without disrupting the integrity of complex physiologically regulated networks. In 2010, our group unexpectedly found that N-[(1r,4r)-4-[2-(7-cyano-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]cyclohexyl]-1H- indole-2-carboxamide (SB269652), a compound supposed to interact with the orthosteric binding site of dopamine receptors, was actually a negative allosteric modulator of D2- and D3-receptor dimers, thus identifying the first allosteric small molecule acting on these important therapeutic targets. This review addresses the progress in understanding the molecular mechanisms of interaction between the negative modulator SB269652 and D2 and D3 dopamine receptor monomers and dimers, and surveys the prospects for developing new dopamine receptor allosteric drugs with SB269652 as the leading compound.
Structure-activity study of N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-ind ole-2-carboxamide (SB269652), a bitopic ligand that acts as a negative allosteric modulator of the dopamine D2 receptor.[Pubmed:26052807]
J Med Chem. 2015 Jul 9;58(13):5287-307.
We recently demonstrated that SB269652 (1) engages one protomer of a dopamine D2 receptor (D2R) dimer in a bitopic mode to allosterically inhibit the binding of dopamine at the other protomer. Herein, we investigate structural determinants for allostery, focusing on modifications to three moieties within 1. We find that orthosteric "head" groups with small 7-substituents were important to maintain the limited negative cooperativity of analogues of 1, and replacement of the tetrahydroisoquinoline head group with other D2R "privileged structures" generated orthosteric antagonists. Additionally, replacement of the cyclohexylene linker with polymethylene chains conferred linker length dependency in allosteric pharmacology. We validated the importance of the indolic NH as a hydrogen bond donor moiety for maintaining allostery. Replacement of the indole ring with azaindole conferred a 30-fold increase in affinity while maintaining negative cooperativity. Combined, these results provide novel SAR insight for bitopic ligands that act as negative allosteric modulators of the D2R.