139180-30-6

Basic information

• Product Name: ZM 241385
• Synonyms: 4-(2-[7-AMINO-2-(2-FURYL)[1,2,4]TRIAZOLO[2,3-A][1,3,5]TRIAZIN-5-YLAMINO]ETHYL)PHENOL;ZM 241385;4-(2-(7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino)ethyl)phenol;4-(2-[7-AMINO-2-(2-FURYL)[1,2,4]TRIAZOLO[2,3-A][1,3,5]TRIAZIN-5-YLAMINO]ETHYL)PHENO;Phenol, 4-[2-[[7-amino-2-(2-furanyl)[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl]amino]ethyl]-
• CAS NO: 139180-30-6
• Molecular Formula: C₁₆H₁₅N₇O₂
• Molecular Weight: 337.34
• Product Categories: Adenosine
• Mol File: 139180-30-6.mol

Chemical Properties

• Appearance: white to tan/
• Density: 1.59 g/cm³
• Refractive Index: 1.791
• Storage Temp.: Store at RT
• Solubility: DMSO: >15mg/mL
• PKA: 10.03±0.15(Predicted)
• CAS DataBase Reference: ZM 241385(CAS DataBase Reference)
• NIST Chemistry Reference: ZM 241385(139180-30-6)
• EPA Substance Registry System: ZM 241385(139180-30-6)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 46
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 139180-30-6(Hazardous Substances Data)

Usage

Biochem/physiol Actions

ZM 241385 is a potent selective adenosine A2A antagonist. The A2A receptor plays a role in regulating myocardial oxygen consumption and coronary blood flow and is highly expressed in the brain, where it has important roles in the regulation of glutamate and dopamine release. ZM 241385 has neuroprotective effects and is being investigated for use in Parkinson′s and other neurodegenerative disorders.

InChI:InChI=1/C16H15N7O2/c17-14-20-15(18-8-7-10-3-5-11(24)6-4-10)21-16-19-13(22-23(14)16)12-2-1-9-25-12/h1-6,9,24H,7-8H2,(H3,17,18,19,20,21,22)

Upstream product

• 51-67-2 tyrosamine 
• 139181-28-5 7-amino-2-(2-furyl)-5-methylsulfonyl<1,2,4>triazolo<1,5-a><1,3,5>triazine 
• 6053-32-3 N-(furan-2-ylcarbonyl)carbonohydrazonic diamide 
• 3663-61-4 3-Amino-5-(furan-2-yl)-1H-1,2,4-triazole 
• 139181-27-4 LUF₅₄₄₃ 
• 3326-71-4 2-furoic acid hydrazide 
• 114953-87-6 5-furan-2-yl-3-methyl-1H-[1,2,4]triazole 
• 617-90-3 2-furancarbonitrile 

Downstream Products

• 139180-31-7 7-amino-2-(furan-2-yl)-5-[2-(4-pivaloyloxyphenyl)ethyl]amino-[1,2,4]triazolo[1,5-a][1,3,5]triazine 
• 1436428-60-2 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 
• 1436428-61-3 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 
• 1436428-62-4 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 
• 1436428-63-5 4-(2-((7-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5yl)amino)ethyl)phenyl acetate 
• 1436428-64-6 4-(2-((7-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5yl)amino)ethyl)phenyl butyrate 
• 1436428-65-7 4-(2-((7-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5yl)amino)ethyl)phenyl decanoate 

Relevant articles and documents

Synthesis, molecular structure, NMR spectroscopic and computational analysis of a selective adenosine A2A antagonist, ZM 241385

Herein, we describe the synthesis of the adenosine A2A antagonist ZM 241385 (9) starting from commercially available 2-furanhydrazide (1) and including a comprehensive structural characterization of all the intermediates and the final product.

Synthesis and pharmacological evaluation of dual acting ligands targeting the adenosine A2A and dopamine D2 receptors for the potential treatment of parkinsons disease

A relatively new strategy in drug discovery is the development of dual acting ligands. These molecules are potentially able to interact at two orthosteric binding sites of a heterodimer simultaneously, possibly resulting in enhanced subtype selectivity, higher affinity, enhanced or modified physiological response, and reduced reliance on multiple drug administration regimens. In this study, we have successfully synthesized a series of classical heterobivalent ligands as well as a series of more integrated and drug-like dual acting molecules, incorporating ropinirole as a dopamine D2 receptor agonist and ZM 241385 as an adenosine A2A receptor antagonist. The best compounds of our series maintained the potency of the original pharmacophores at both receptors (adenosine A2A and dopamine D2). In addition, the integrated dual acting ligands also showed promising results in preliminary blood-brain barrier permeability tests, whereas the classical heterobivalent ligands are potentially more suited as pharmacological tools.

Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space

Growing evidence has suggested a role in targeting the adenosine A 2A receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A2A receptor were synthesized and tested in a recombinant human adenosine A2A receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A2A receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A2A receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position.

125I-4-(2-[7-amino-2-{2-furyl}{1,2,4}triazolo{2,3- a}{1,3,5}triazin-5-yl-amino]ethyl)phenol, a high affinity antagonist radioligand selective for the A(2a) adenosine receptor

The A(2a) adenosine receptor (AR) mediates several important physiological effects of adenosine, including vasodilation and inhibition of platelet aggregation. Until recently, no antagonist radioligand of sufficient selectivity or affinity was available.

[1,2,4]-Triazolo[1,5-a]and pyrazolo[2,3-a][1,3,5]triazine derivatives

The invention concerns novel, pharmaceutically useful compounds of formula I in which Q is a 5-membered heteroaryl optionally bearing 1 or 2 substituents independently selected from (1-4C)alkyl and halogeno; R1 is hydrogen, (1-6C)alkyl, or (1-4

Heterocyclic compounds

A compound of the formula I STR1 wherein: A 1 and A 2 are each independently N or CT in which T is hydrogen or (1-4C)alkyl;R 1 and R 2 are each independently hydrogen, (1-6C)alkyl, or (1-4C)alkanoyl;X 1 and X 2 are each independently O, S or NH; andL is a