CGS 21680 hydrochloride

Base Information

• Chemical Name: CGS 21680 hydrochloride
• CAS No.: 124431-80-7
• Molecular Formula: C23H29 N7 O6 . Cl H
• Molecular Weight: 535.987
• DSSTox Substance ID: DTXSID2040999
• Wikipedia: CGS-21680
• ChEMBL ID: CHEMBL537419
• Mol file: 124431-80-7.mol

Synonyms:2-(4-(2-carboxyethyl)phenethylamino)-5'-N-ethylcarboxamidoadenosine;2-p-(2-carboxyethyl)phenethylamino-5'-N-ethylcarboxamidoadenosine hydrochloride;Benzenepropanoic acid, 4-(2-((6-amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl)amino)ethyl)-;CGS 21680;CGS 21680A;CGS-21680C;CGS21680

Chemical Property of CGS 21680 hydrochloride

Chemical Property:

• Melting Point: 204-206°C
• PSA: 197.74000
• LogP: 1.68270
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 535.1946094
• Heavy Atom Count: 37
• Complexity: 755

Purity/Quality:

99% ^*data from raw suppliers

CGS 21680A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC(=O)C1C(C(C(O1)N2C=NC3=C(N=C(N=C32)NCCC4=CC=C(C=C4)CCC(=O)O)N)O)O.Cl
• Isomeric SMILES: CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=C(N=C32)NCCC4=CC=C(C=C4)CCC(=O)O)N)O)O.Cl
• Uses: CGS 21680A is a potent, selective agonist of the adenosine A2A receptor (Ki = 11-46 nM). It is less effective at adenosine A1 and A3 receptors (Kis = 0.5-3.1 and 0.6-1 μM, respectively) and is without effect at adenosine A2B (Ki > 10 μM). CGS 21680A is commonly used to study the actions of the adenosine A2A receptor in cells and tissues.[Cayman Chemical] Adenosine receptors are related to many diseases such as cardiovascular, autoimmune, and cancer. CGS 21680 is a potent and selective agonist of the adenosine A2A receptor, a member of G protein coupled receptor (1,2,3).

Technology Process of CGS 21680 hydrochloride

There total 9 articles about CGS 21680 hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2-<<4-<2-(tert-butoxycarbonyl)etyl>phenethyl>amino>-2',3'-O-isopropylideneadenosine-5'-N-ethylcarboxamide (120225-76-5) → 2-p-(2-carboxyethyl)phenethylamino-5'-N-ethylcarboxamidoadenosine hydrochloride (124431-80-7)

Guidance literature:

With hydrogenchloride; at 65 ℃; for 1h;

DOI:10.1021/jm00169a015

Reference yield:

4-Bromophenylacetonitrile (16532-79-9) → 2-p-(2-carboxyethyl)phenethylamino-5'-N-ethylcarboxamidoadenosine hydrochloride (124431-80-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 105 g / Pd(OAc)2, tri-o-tolylphosphine / triethylamine / 6 h / Heating

2: 84 percent / 1 N HCl, H₂ / 10percent Pd/C / propan-2-ol / 7 h / 2585.7 Torr / Heating

3: 55 percent / 3 h / 130 °C

4: 96 percent / 1 N HCl / 1 h / 65 °C

With hydrogenchloride; palladium diacetate; hydrogen; tris-(o-tolyl)phosphine; palladium on activated charcoal; In triethylamine; isopropyl alcohol;

DOI:10.1021/jm00169a015

Reference yield:

(E)-tert-butyl 3-(4-(cyanomethyl)phenyl)acrylate (120225-74-3) → 2-p-(2-carboxyethyl)phenethylamino-5'-N-ethylcarboxamidoadenosine hydrochloride (124431-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / 1 N HCl, H₂ / 10percent Pd/C / propan-2-ol / 7 h / 2585.7 Torr / Heating

2: 55 percent / 3 h / 130 °C

3: 96 percent / 1 N HCl / 1 h / 65 °C

With hydrogenchloride; hydrogen; palladium on activated charcoal; In isopropyl alcohol;

DOI:10.1021/jm00169a015

upstream raw materials:

2-<<4-<2-(tert-butoxycarbonyl)etyl>phenethyl>amino>-2',3'-O-isopropylideneadenosine-5'-N-ethylcarboxamide

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

4-Bromophenylacetonitrile

(E)-tert-butyl 3-(4-(cyanomethyl)phenyl)acrylate

Downstream raw materials:

C₃₀H₄₃N₉O₇

C₂₇H₃₇N₉O₆

Refernces

• 1、 Hutchison, Alan J.,Williams, Michael,Jesus, Reynalda, de,Yokoyama, Rina,Oei, Howard H.,et al.. "2-(Arylalkylamino)adenosin-5'-uronamides: A New Class of Highly Selective Adenosine A2 Receptor Ligands". . p. 1919 - 1924. Retrieved 2007/10/02.