5728-16-5

Basic information

• Product Name: 3-Chloro-4-methoxy-1,2,5-thiadiazole
• Synonyms: 3-Chloro-4-methoxy-1,2,5-thiadiazole
• CAS NO: 5728-16-5
• Molecular Formula: C₃H₃ClN₂OS
• Molecular Weight: 150.58672
• EINECS: 944-002-8
• Mol File: 5728-16-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Chloro-4-methoxy-1,2,5-thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-4-methoxy-1,2,5-thiadiazole(5728-16-5)
• EPA Substance Registry System: 3-Chloro-4-methoxy-1,2,5-thiadiazole(5728-16-5)

Safety Data

• Hazardous Substances Data: 5728-16-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-4-methoxy-1,2,5-thiadiazole is used as a reactant for the preparation of selective ligands at human 5-HT1A receptors. These ligands play a crucial role in the development of medications targeting various neurological and psychiatric disorders, such as anxiety, depression, and schizophrenia. 3-Chloro-4-methoxy-1,2,5-thiadiazole's unique structure allows for the creation of ligands with high specificity and affinity for the 5-HT1A receptors, leading to more effective treatments.

Upstream product

• 13369-03-4 Cyan-imidoameisensaeuremethylester 
• 124-41-4 sodium methylate 
• 5728-20-1 3,4-dichloro-1,2,5-thiadiazole 
• 67-56-1 methanol 

Downstream Products

• 32909-92-5 sulfametrole 
• 7716-66-7 3-chloro-1,2-benzisothiazole 
• 40991-38-6 3-methoxy-1,2-benzoisothiazole 

Relevant articles and documents

Evaluation of 1,2,5-thiadiazoles as modulators of M1/M 5 muscarinic receptor subtypes

Studies have demonstrated the presence of allosteric binding sites on each of the muscarinic acetylcholine receptor (mAChR) subtypes. Since most drugs targeting muscarinic receptors bind to the highly conserved orthosteric binding site, they fail to achieve appreciable subtype selectivity. Targeting non-conserved allosteric sites may provide a new way of enhancing selectivity for individual subtypes of muscarinic receptor. Tetra(ethyleneglycol)(3-methoxy- 1,2,5-thiadiazol-4-yl)[3-(1-methyl-1,2,5,6-tetrahydropyrid-3-yl)-1,2, 5-thiadiazol-4-yl] ether, CDD-0304 (10), was found to be a M1/2/4 selective muscarinic agonist and might prove useful in treating the symptoms associated with schizophrenia (J. Med. Chem. 2003, 46, 4273). It was hypothesized that the observed subtype selectivity demonstrated by 10 may be due to its ability to function as a bitopic ligand (J. Med. Chem. 2006, 49, 7518). To further investigate this possibility, a novel series of compounds was synthesized using a 1,2,5-thiadiazole moiety along with varying lengths of a polyethylene glycol linker and terminal groups, for evaluation as potential allosteric modulators of muscarinic receptors. Preliminary biological studies were performed using carbachol to stimulate M1 and M5 receptors. No significant agonist activity was observed at either M1 or M5 receptors for any of the compounds. Compound 18, 2-(4-methoxy-1,2,5-thiadiazol-3-yloxy)-N,N-dimethylethanamine fumarate (CDD-0361F) was found to block the effects of carbachol at M5 muscarinic receptors.

Synthesis and biological characterization of 1-methyl-1,2,5,6-tetrahydropyridyl-1,2,5-thiadiazole derivatives as muscarinic agonists for the treatment of neurological disorders

Muscarinic agonists might be useful in the treatment of neurological disorders, including Alzheimer's disease, schizophrenia, chronic pain, and drug abuse. Previous studies identified a series of bis-1,2,5-thiadiazole derivatives of 1,2,5,6-tetrahydropyridine with high activity and selectivity for muscarinic receptors. To develop compounds with improved central nervous system penetration, several new derivatives were synthesized and characterized for muscarinic receptor binding and activity. One ligand (11) exhibited agonist activity at M1, M2, and M4 receptors, a selectivity profile suggesting potential utility in the treatment of schizophrenia.

1,2,5-Thiadiazole derivatives are potent and selective ligands at human 5-HT1A receptors

Amino acid derivatives of 1,2,5-thiadiazol-3-yl-piperazine related to (+)-WAY-100135 and WAY-100635 are potent 5-HT1A receptor agonists and antagonists, which have selective affinity for 5-HT1A receptors versus α and dopamine (D2, D3, and D4) receptors.

METHOD FOR TREATING ANXIETY

The present invention provides a method for treating anxiety in humans using azacyclic or azabicyclic compounds.

HETEROCYCLIC COMPOUNDS AND THEIR PREPARATION AND USE

The present invention relates to therapeutically active azacyclic or azabicyclic compounds, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in treating diseases in the central nervous system caused by malfunctioning of the muscarinic cholinergic system.