19666-40-1

Basic information

• Product Name: 2-(3-CHLOROPROPYL)-1,2,4-TRIAZOL-[4,3-A]PYRIDINE-3 (2H)-ONE
• Synonyms: 2-(3-CHLOROPROPYL)-1,2,4-TRIAZOL-[4,3-A]PYRIDINE-3 (2H)-ONE;2-(3-Chloropropyl)-1,2,4-triazolo[4,3-a]pyridine-3(2H)-one;2-(3-Chloropropyl)-1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one
• CAS NO: 19666-40-1
• Molecular Formula: C₉H₁₀ClN₃O
• Molecular Weight: 211.65
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Aromatics, Heterocycles, Miscellaneous Reagents
• Mol File: 19666-40-1.mol

Chemical Properties

• Melting Point: 73-75 °C
• Boiling Point: 315.5±44.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• PKA: 1.07±0.20(Predicted)
• CAS DataBase Reference: 2-(3-CHLOROPROPYL)-1,2,4-TRIAZOL-[4,3-A]PYRIDINE-3 (2H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-CHLOROPROPYL)-1,2,4-TRIAZOL-[4,3-A]PYRIDINE-3 (2H)-ONE(19666-40-1)
• EPA Substance Registry System: 2-(3-CHLOROPROPYL)-1,2,4-TRIAZOL-[4,3-A]PYRIDINE-3 (2H)-ONE(19666-40-1)

Safety Data

• Hazardous Substances Data: 19666-40-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-(3-Chloropropyl)-1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one is used as a key intermediate in the synthesis of triazolopyridine derivatives. These derivatives are of significant interest for their potential therapeutic applications, particularly in the development of new drugs targeting specific receptors.
Used in the Synthesis of Trazadone Analogs:
In the field of psychopharmacology, 2-(3-Chloropropyl)-1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one is utilized in the synthesis of Trazadone analogs. Trazadone is a medication primarily used to treat major depressive disorder and has also been studied for its off-label use in treating insomnia and erectile dysfunction. The synthesized analogs are evaluated for their binding affinity to 5HT (2A and α1) receptors, which are crucial for understanding their potential antidepressant and anxiolytic effects.
Used in Medicinal Chemistry:
2-(3-Chloropropyl)-1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one serves as a building block in the design and synthesis of novel compounds with improved pharmacological properties. Its unique structure allows for the development of molecules with enhanced binding affinities, selectivity, and bioavailability, making it a valuable component in the creation of new drugs for various therapeutic areas.

Upstream product

• 109-70-6 1.3-chlorobromopropane 
• 6969-71-7 [1,2,4]triazolo[4,3-a]pyridin-3(2H)-one 
• 632-02-0 3-chloropropyl p-toluenesulfonate 
• 4930-98-7 pyrid-2-ylhydrazine 
• 109-04-6 2-bromo-pyridine 
• 109-09-1 2-chloropyridine 

Downstream Products

• 220910-12-3 2-(3-((2-((3-chlorophenyl)amino)ethyl)amino)propyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one 
• 25332-39-2 trazodone hydrochloride 
• 19794-93-5 trazodone 

Relevant articles and documents

Microwave-assisted synthesis of trazodone and its derivatives as new 5-HT1A ligands: Binding and docking studies

Trazodone, a well-known antidepressant drug widely used throughout the world, works as a 5-hydroxytryptamine (5-HT2) and α1-adrenergic receptor antagonist and a serotonin reuptake inhibitor. Our research aimed to develop a new method for the synthesis of trazodone and its derivatives. In the known methods of the synthesis of trazodone and its derivatives, organic and toxic solvents are used, and the synthesis time varies from several to several dozen hours. Our research shows that trazodone and its derivatives can be successfully obtained in the presence of potassium carbonate as a reaction medium in the microwave field in a few minutes. As a result of the research work, 17 derivatives of trazodone were obtained, including compounds that exhibit the characteristics of 5-HT1A receptor ligands. Molecular modeling studies were performed to understand the differences in the activity toward 5-HT1A and 5-HT2A receptors between ligand 10a (2-(6-(4-(3-chlorophenyl)piperazin-1-yl)hexyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one) (5-HT1A Ki = 16 nM) and trazodone. The docking results indicate the lack of the binding of ligand 10a to 5-HT2AR, which is consistent with the in vitro studies. On the other hand, the docking results for the 5-HT1A receptor indicate two possible binding modes. Crystallographic studies support the hypothesis of an extended conformation.

Substituted-3-indolyl-4-piperidino-alkyl heterocycles for the treatment of depression

A compound represented by the formula I: wherein A represents the following heterocycles: and R1-9 are as defined herein, a composition containing this compound and methods for treating disorders of the serotonin-affected neurological systems u

Treatment of sleeping disorders using CNS sleep target modulators

The invention is directed to compositions used for treating sleep disorders. In addition, the invention provides convenient methods of treatment of a sleep disorder. Furthermore, the invention provides methods of treating sleep disorders using composition