4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenol

Base Information

• Chemical Name: 4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenol
• CAS No.: 139180-30-6
• Molecular Formula: C16H15N7O2
• Molecular Weight: 337.341
• European Community (EC) Number: 689-671-4
• UNII: 5NIC36BO71
• DSSTox Substance ID: DTXSID80160954
• Nikkaji Number: J679.659A
• Wikipedia: ZM-241,385
• Wikidata: Q8063128
• Pharos Ligand ID: 1DSPZ1GWBXFY
• Metabolomics Workbench ID: 151885
• ChEMBL ID: CHEMBL113142
• Mol file: 139180-30-6.mol

Synonyms:4-(2-(7-amino-2-(2-furyl)-(1,2,4)triazolo(2,3-a)-(1,3,5)triazin-5-yl-amino)ethyl)phenol;ZM 241385;ZM-241385;ZM241385

Chemical Property of 4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenol

Chemical Property:

• Refractive Index: 1.791
• PKA: 10.03±0.15(Predicted)
• PSA: 127.39000
• Density: 1.59 g/cm³
• LogP: 2.37590
• Storage Temp.: Store at RT
• Solubility.: DMSO: >15mg/mL
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 337.12872275
• Heavy Atom Count: 25
• Complexity: 435

Purity/Quality:

97% ^*data from raw suppliers

ZM 241385 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 46

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=COC(=C1)C2=NN3C(=NC(=NC3=N2)NCCC4=CC=C(C=C4)O)N

Technology Process of 4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenol

There total 7 articles about 4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenol 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: 33.0%

tyrosamine (51-67-2) + 7-amino-2-(2-furyl)-5-methylsulfonyl<1,2,4>triazolo<1,5-a><1,3,5>triazine (139181-28-5) → 4-[2-(7-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino)-ethyl]-phenol (139180-30-6)

Guidance literature:

In acetonitrile; at 20 ℃;

DOI:10.1016/j.bmcl.2013.03.070

Reference yield:

N-(furan-2-ylcarbonyl)carbonohydrazonic diamide (6053-32-3) → 4-[2-(7-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino)-ethyl]-phenol (139180-30-6)

Guidance literature:

Multi-step reaction with 4 steps

1: water / 1 h / 140 °C / 4500.45 Torr / Microwave irradiation

2: 1 h / 170 °C / Inert atmosphere

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 22 h / -5 - 20 °C

4: acetonitrile / 20 °C

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.bmcl.2013.03.070

Reference yield:

3-Amino-5-(furan-2-yl)-1H-1,2,4-triazole (3663-61-4) → 4-[2-(7-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino)-ethyl]-phenol (139180-30-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1 h / 170 °C / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 22 h / -5 - 20 °C

3: acetonitrile / 20 °C

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;

DOI:10.1016/j.bmcl.2013.03.070

upstream raw materials:

tyrosamine

7-amino-2-(2-furyl)-5-methylsulfonyl<1,2,4>triazolo<1,5-a><1,3,5>triazine

N-(furan-2-ylcarbonyl)carbonohydrazonic diamide

3-Amino-5-(furan-2-yl)-1H-1,2,4-triazole

Downstream raw materials:

7-amino-2-(furan-2-yl)-5-[2-(4-pivaloyloxyphenyl)ethyl]amino-[1,2,4]triazolo[1,5-a][1,3,5]triazine

ethyl 4-(4-(2-((7-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)-phenoxy)butanoate

ethyl 4-((2-(furan-2-yl)-5-((4-hydroxyphenethyl)amino)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-yl)amino)butanoate

ethyl 4-((5-((4-(4-ethoxy-4-oxobutoxy)phenethyl)amino)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-yl)amino)butanoate

Refernces

Synthesis, biological assays and QSAR studies of N-(9-benzyl-2-phenyl-8-azapurin-6-yl)-amides as ligands for A₁ adenosine receptors

10.1016/j.bmc.2009.01.060

This research aims to synthesize and evaluate a series of 2-phenyl-9-benzyl-8-azapurines with an amido group at the 6 position as potential ligands for adenosine receptors, particularly focusing on the A1 subtype. The study involves synthesizing compounds with various substituents at the 6 position and testing their affinity for A1, A2A, and A3 adenosine receptors through radioligand binding assays. The results show that many of these compounds exhibit high affinity and selectivity for the A1 receptor compared to A2A and A3 receptors. Based on the biological data, QSAR models were developed using multiple linear regression and decision trees to predict the activity of new compounds. The models suggest that certain structural features, such as the presence of a cyclohexyl group, contribute to high affinity and selectivity for the A1 receptor. The study concludes that these findings can guide the design of new selective A1 adenosine receptor ligands, which have potential therapeutic applications. Key chemicals used in the research include 2-phenyl-9-benzyl-8-azapurines, various acyl chlorides for introducing different substituents, and radioligands like [3H]DPCPX, [3H]ZM241385, and [3H]NECA for binding assays.