120225-54-9

Basic information

• Product Name: CGS 21680
• Synonyms: 1-Deoxy-1-[6-amino-2-[2-[4-(2-carboxyethyl)phenyl]ethylamino]-9H-purin-9-yl]-N-ethyl-β-D-ribofuranuronamide;2-[[2-[4-(2-Carboxyethyl)phenyl]ethyl]amino]-5'-ethylamino-5'-oxo-5'-deoxyadenosine;2-[[2-[4-(3-Hydroxy-3-oxopropyl)phenyl]ethyl]amino]-5'-deoxy-5'-oxo-5'-(ethylamino)adenosine;2-(4-(2-Carboxyethyl)phenethylamino)-5'-N-ethylcarboxamidoadenosine;Benzenepropanoic acid, 4-(2-((6-amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl)amino)ethyl)-;C061282;Cgs-21680c;4-[2-[[6-Amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid
• CAS NO: 120225-54-9
• Molecular Formula: C₂₃H₂₉N₇O₆
• Molecular Weight: 499.51966
• Mol File: 120225-54-9.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• Density: 1.60
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Soluble up to 3.4 mg/mL in DMSO and 20 mg/mL in 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin.
• PKA: 4.67±0.10(Predicted)
• CAS DataBase Reference: CGS 21680(CAS DataBase Reference)
• NIST Chemistry Reference: CGS 21680(120225-54-9)
• EPA Substance Registry System: CGS 21680(120225-54-9)

Safety Data

• Hazardous Substances Data: 120225-54-9(Hazardous Substances Data)

Usage

Uses

CGS 21680 hydrochloride is currently used in research in studying neuronal transmission, also in respiration. CGS 21680 is commonly used to study the actions of the adenosine A2A receptor in cells and tissues. CGS 21680 HCl is an adenosine A2 receptor agonist with IC50 of 22 nM, exhibits 140-fold over A1 receptor. CGS 21680C effectively increases coronary flow with an ED25 value of 1.8 nM. In hippocampal slices, CGS 21680 apis weak agonist on pre- and postsynaptic measures of electrophysiologicaJ activity.

Definition

ChEBI: A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and the hydrogen at position 2 on the adenine is replaced by a 4-(2-carboxyethyl)phenethylamino group.

Biological Activity

cgs 21680 is a selective agonists of a2 adenosine receptor with ic50 value of 22nm [1].cgs 21680 is found to be potent and selective adenosine a2 receptor agonists. in a radioligand binding in vitro assay, cgs 21680 binds a2 receptor with ic50 value of 22nm and the a1/a2 ratio is 141, in the perfused rat heart model, cgs 21680 can increase coronary flow with greater ec25 value than 1000nm. it shows a good separation between its ability to induce vasorelaxation and bradycardia. cgs 21680 also has potent effect on blood pressure in vivo with ec25 value of 9μg/kg and it can induce an increase in heart rate [1].it is reported that cgs 21680 also has the potency of anti-inflammatory. it can reduce the development of acute lung inflammation in a mouse model of carrageenan-induced pleurisy. in both prior and post-treatment, cgs 21680 can reduce the number of inflammatory cells and the degree of lung injury [2].

references

[1] alan j. hutchison, randy l. webb, howard h. oei, geetha r. ghai, mark b. zimmerman and michael williams. cgs 21680c, an a2 selective adenosine receptor agonist with preferential hypotensive activity. the journal of pharmacology and experimental therapeutics. 1989, 25 (1): 47-55.[2] daniela impellizzeri, rosanna di paola, emanuela esposito, emanuela mazzon, irene paterniti, alessia melani, placido bramanti, felicita pedata, salvatore cuzzocrea. cgs 21680, an agonist of the adenosine (a2a) receptor, decreases acute lung inflammation. european journal of pharmacology. 2011, 68: 305-316.

Downstream Products

• 1352627-63-4 (R)-2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-3-(1H-imidazol-4-yl)propanoic acid 
• 1352627-48-5 (R)-methyl 2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-3-(1H-imidazol-4-yl)propanoate 
• 1352627-62-3 (S)-2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-3-(1H-imidazol-4-yl)propanoic acid 
• 1352627-47-4 (S)-methyl 2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-3-(1H-imidazol-4-yl)propanoate 
• 1352627-52-1 (R)-2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)succinic acid 
• 1352627-50-9 (S)-2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)succinic acid 
• 1352627-59-8 (R)-2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-3-phenylpropanoic acid 
• 1352627-44-1 (R)-methyl 2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-3-phenylpropanoate 
• 1352627-40-7 (R)-dimethyl 2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)succinate 
• 1352627-57-6 (S)-2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-3-phenylpropanoic acid 
• 1352627-43-0 (S)-methyl 2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-3-phenylpropanoate 
• 1352627-41-8 (S)-methyl 2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-5-guanidinopentanoate 
• 1352645-62-5 (R)-2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-5-guanidinopentanoic acid 
• 1352627-42-9 (R)-methyl 2-(3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanamido)-5-guanidinopentanoate