1,2,4-Triazolo(3,4-a)phthalazin-6-amine, N,N-bis(2-methoxyethyl)-3-(4-methoxyphenyl)-

Base Information

• Chemical Name: 1,2,4-Triazolo(3,4-a)phthalazin-6-amine, N,N-bis(2-methoxyethyl)-3-(4-methoxyphenyl)-
• CAS No.: 87540-22-5
• Molecular Formula: C22H25N5O3
• Molecular Weight: 407.4656
• DSSTox Substance ID: DTXSID70236410
• Wikidata: Q83118364
• ChEMBL ID: CHEMBL273456

Synonyms:BRN 4768157;1,2,4-Triazolo(3,4-a)phthalazin-6-amine, N,N-bis(2-methoxyethyl)-3-(4-methoxyphenyl)-;CHEMBL273456;N,N-Bis(2-methoxyethyl)-3-(4-methoxyphenyl)-1,2,4-triazolo(3,4-a)phthalazin-6-amine;87540-22-5;SCHEMBL10876687;DTXSID70236410;C22H25N5O3;BDBM50018805;C22-H25-N5-O3;LS-156550;Bis-(2-methoxy-ethyl)-[3-(4-methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-amine

Chemical Property of 1,2,4-Triazolo(3,4-a)phthalazin-6-amine, N,N-bis(2-methoxyethyl)-3-(4-methoxyphenyl)-

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.25g/cm³
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 407.19573968
• Heavy Atom Count: 30
• Complexity: 511

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCCN(CCOC)C1=NN2C(=NN=C2C3=CC=CC=C31)C4=CC=C(C=C4)OC

Technology Process of 1,2,4-Triazolo(3,4-a)phthalazin-6-amine, N,N-bis(2-methoxyethyl)-3-(4-methoxyphenyl)-

There total 3 articles about 1,2,4-Triazolo(3,4-a)phthalazin-6-amine, N,N-bis(2-methoxyethyl)-3-(4-methoxyphenyl)- 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: 75.0%

Bis-(2-methoxyethyl)amine (111-95-5) + 6-chloro-3-(4-methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazine (98123-77-4) → L 16317 (87540-22-5)

Guidance literature:

at 140 ℃; for 30h;

DOI:10.1021/jm00401a010

Reference yield:

1-chloro-4-hydrazinophthalazine (51935-42-3,59275-72-8) → L 16317 (87540-22-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Et₃N / dioxane / 5 h / Heating

2: 75 percent / 30 h / 140 °C

With triethylamine; In 1,4-dioxane;

DOI:10.1021/jm00401a010

Reference yield:

4-methoxy-benzoyl chloride (100-07-2) → L 16317 (87540-22-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Et₃N / dioxane / 5 h / Heating

2: 75 percent / 30 h / 140 °C

With triethylamine; In 1,4-dioxane;

DOI:10.1021/jm00401a010

upstream raw materials:

Bis-(2-methoxyethyl)amine

6-chloro-3-(4-methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazine

1-chloro-4-hydrazinophthalazine

4-methoxy-benzoyl chloride

Refernces

6-(Alkylamino)-3-aryl-1,2,4-triazolo<3,4-a>phthalazines. A New Class of Benzodiazepine Receptor Ligands

10.1021/jm00401a010

The research investigates a new class of compounds that interact with benzodiazepine (BZ) receptors, aiming to develop antianxiety agents without nonspecific central nervous system (CNS) depressant side effects. The study synthesized and tested various 6-(alkylamino)-3-aryl-1,2,4-triazolo[3,4-a]phthalazines for their ability to displace diazepam from rat brain binding sites in vitro and their anticonvulsant and anticonflict properties in vivo. Key chemicals used include diazepam as a reference, [3H]diazepam for radioligand binding assays, and a range of synthesized compounds such as 3-aryl-6-chloro-1,2,4-triazolo[3,4-a]phthalazines and their derivatives. The findings revealed that some compounds, like N~-bis(2-methoxyethyl)-3-(4-methoxyphenyl)-1,2,4-triazolo[3,4-a]phthalazin-6-amine (80), showed significant binding affinity and anticonflict activity without impairing motor coordination at lower doses, suggesting selective anxiolytic activity. The study concludes that these compounds could represent a new class of BZ receptor ligands with potential therapeutic applications, though further research is needed to explore their clinical relevance and species-dependent effects.

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