131986-28-2

Basic information

• Product Name: 3-CHLORO-4-(PYRIDIN-3-YL)-1,2,5-THIADIAZOLE
• Synonyms: 3-CHLORO-4-(PYRIDIN-3-YL)-1,2,5-THIADIAZOLE;3-(4-CHLORO-1,2,5-THIADIAZOL-3-YL)PYRIDINE;3-Chloro-4-(3-pyridyl)-1,2,5-thiadiazole, 95%;Pyridine, 3-(4-chloro-1,2,5-thiadiazol-3-yl)-
• CAS NO: 131986-28-2
• Molecular Formula: C₇H₄ClN₃S
• Molecular Weight: 197.64
• Mol File: 131986-28-2.mol

Chemical Properties

• Melting Point: 56℃
• Boiling Point: 297.197 °C at 760 mmHg
• Flash Point: 133.54 °C
• Appearance: /
• Density: 1.455 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.631
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-CHLORO-4-(PYRIDIN-3-YL)-1,2,5-THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-(PYRIDIN-3-YL)-1,2,5-THIADIAZOLE(131986-28-2)
• EPA Substance Registry System: 3-CHLORO-4-(PYRIDIN-3-YL)-1,2,5-THIADIAZOLE(131986-28-2)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 131986-28-2(Hazardous Substances Data)

Usage

Uses

3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole can be used to treat neurological disorders.

InChI:InChI=1/C7H4ClN3S/c8-7-6(10-12-11-7)5-2-1-3-9-4-5/h1-4H

Upstream product

• 131988-63-1 2-amino-2-(pyridin-3-yl)acetonitrile 
• 89878-14-8 3-Diethylboranylpyridine 
• 5728-20-1 3,4-dichloro-1,2,5-thiadiazole 
• 500-22-1 3-pyridinecarboxaldehyde 
• 17604-74-9 2-hydroxy-2-(pyridin-3-yl)acetonitrile 
• 59020-10-9 3-(tributylstannyl)pyridine 
• 537706-14-2 3-chloro-4-iodo-1,2,5-thiadiazole 
• 537706-13-1 3-bromo-4-chloro-1,2,5-thiadiazole 

Downstream Products

• 131987-62-7 3-(3-ethoxy-1,2,5-thiadiazol-4-yl)pyridine 
• 179333-98-3 3-(3-chloro-1,2,5-thiadiazol-4-yl)-4-methyl-1-phenoxycarbonyl-1,4-dihydropyridine 
• 131987-69-4 3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)pyridine 
• 131987-70-7 3-(3-Benzyloxy-1,2,5-thiadiazol-4-yl)pyridine 
• 1018845-36-7 3-<3-(3-phenyl-2-propyn-1-yloxy)-1,2,5-thiadiazol-4-yl>pyridine 
• 1018845-33-4 3-(3-(4-phenylbutoxy)-1,2,5-thiadiazol-4-yl)pyridine 
• 424829-90-3 3-(3-((3-fluoropropyl)thio)-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine 
• 828254-49-5 3-chloro-4-(1-benzylpyrid-3-yl)-1,2,5-thiadiazole bromide 
• 1018846-18-8 3-(3-(3-(tert-butoxycarbonylamino)propoxy)-1,2,5-thiadiazol-4-yl)pyridine 
• 1018845-85-6 3-(3-(4-(tert-butyldiphenylsiloxy)butoxy)-1,2,5-thiadiazol-4-yl)pyridine 
• 1018845-82-3 3-(3-(3-(tert-butyldiphenylsiloxy)propoxy)-1,2,5-thiadiazol-4-yl)pyridine 
• 1018845-79-8 3-(3-(2-(tert-butyldiphenylsiloxy)ethoxy)-1,2,5-thiadiazol-4-yl)pyridine 
• 159054-94-1 3-(4-benzyloxy-1,2,5-thiadiazol-3-yl)-1,2,5,6-tetrahydro-1-methylpyridine oxalate 
• 131988-19-7 3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide 

Relevant articles and documents

Muscarinic agonists with antipsychotic-like activity: Structure-activity relationships of 1,2,5-thiadiazole analogues with functional dopamine antagonist activity

Muscarinic agonists were tested in two models indicative of clinical antipsychotic activity: conditioned avoidance responding (CAR) in rats and inhibition of apomorphine-induced climbing in mice. The standard muscarinic agonists oxotremorine and pilocarpine were both active in these tests but showed little separation between efficacy and cholinergic side effects. Structure-activity relationships of the alkylthio-1,2,5-thiadiazole azacyclic type muscarinic partial agonists are shown, revealing the exo-6-(3- propyl/butylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane analogues (4a,b and 9a,b) to be the most potent antipsychotic agents with large separation between efficacy and cholinergic side effects. The lack of enantiomeric selectivity suggests the pharmacophoric elements are in the mirror plane of the compounds. A model explaining the potency differences of closely related compounds is offered. The data suggest that muscarinic agonists act as functional dopamine antagonists and that they could become a novel treatment of psychotic patients.

The palladium-catalyzed cross-coupling reactions of 3-chloro-4-halogeno-1,2,5-thiadiazoles

3,4-Dichloro- and 3-chloro-4-halogeno-1,2,5-thiadiazoles (halogeno-: bromo- and iodo-) are involved in Pd-catalyzed cross-coupling reactions under Stille and Suzuki conditions. As a result, by using the commercially available 3,4-dichloro-1,2,5-thiadiazole as substrate, several 3-alkyl-, 3-alkenyl-, 3-alkynyl-and 3-aryl-4-chloro-1,2,5-thiadiazoles can easily be prepared. However, these reactions through direct desymmetrization of the 3,4-dichloro-1,2,5-thiadiazole always occur with side-reactions resulting from the concurrent decomposition of the heterocyclic ring of the starting material. These problems are resolved by involving, in these Pd-catalyzed cross-coupling reactions, the more reactive and selective 3-bromo-4-chloro- and 3-chloro-4-iodo-1,2,5-thiadiazole. These new dihalogeno-1,2,5-thiadiazoles can easily be prepared, via diazotization reaction followed by halogen substitution, from the 3-amino-4-chloro-1,2,5-thiadiazole.

Tacrine-xanomeline and tacrine-iperoxo hybrid ligands: Synthesis and biological evaluation at acetylcholinesterase and M1 muscarinic acetylcholine receptors

We synthesized a set of new hybrid derivatives (7-C8, 7-C10, 7-C12 and 8-C8, 8-C10, 8-C12), in which a polymethylene spacer chain of variable length connected the pharmacophoric moiety of xanomeline, an M1/M4-preferring orthosteric muscarinic agonist, with that of tacrine, a well-known acetylcholinesterase (AChE) inhibitor able to allosterically modulate muscarinic acetylcholine receptors (mAChRs). When tested in vitro in a colorimetric assay for their ability to inhibit AChE, the new compounds showed higher or similar potency compared to that of tacrine. Docking analyses were performed on the most potent inhibitors in the series (8-C8, 8-C10, 8-C12) to rationalize their experimental inhibitory power against AChE. Next, we evaluated the signaling cascade at M1 mAChRs by exploring the interaction of Gαq-PLC-β3 proteins through split luciferase assays and the myo-Inositol 1 phosphate (IP1) accumulation in cells. The results were compared with those obtained on the known derivatives 6-C7 and 6-C10, two quite potent AChE inhibitors in which tacrine is linked to iperoxo, an exceptionally potent muscarinic orthosteric activator. Interestingly, we found that 6-C7 and 6-C10 behaved as partial agonists of the M1 mAChR, at variance with hybrids 7-Cn and 8-Cn containing xanomeline as the orthosteric molecular fragment, which were all unable to activate the receptor subtype response.

Hybrid molecules from xanomeline and tacrine: Enhanced tacrine actions on cholinesterases and muscarinic M1 receptors

A set of amide- and amine-linked hybrid molecules comprising moieties of the orthosteric M1 muscarinic receptor agonist xanomeline and the Cholinesterase inhibitor and allosteric receptor modulator tacrine were prepared with varying spacer length of 10-17 atoms. The hybrids inhibited acetylcholinesterase with similar or higher potency compared to tacrine. M 1 receptor binding affinity was similar or higher relative to xanomeline and far higher relative to tacrine. Affinities hardly changed when the receptors' orthosteric site was occupied by an inverse agonist ligand. When occupied by the orthosteric activator acetylcholine, affinity for the hybrids declined to unmeasureably low levels. Hybrids did not activate M1 receptors. In vivo studies assaying cognition impairment in rats induced by scopolamine revealed pronounced enhancement of scopolamine action. Taken together, instead of dualsteric (simultaneous allosteric/orthosteric) binding, the hybrids seem to prefer purely allosteric binding at the inactive M 1 receptor.

Synthesis and evaluation of xanomeline analogs-Probing the wash-resistant phenomenon at the M1 muscarinic acetylcholine receptor

A series of xanomeline analogs were synthesized and evaluated for binding at the M1 muscarinic acetylcholine receptor (M1 receptor). Specifically, compounds that substitute the O-hexyl chain of xanomeline with polar, ionizable, or conformationally restricted moieties were assessed for their ability to bind to the M1 receptor in a wash-resistant manner (persistent binding). From our screen, several novel ligands that persistently bind to the M1 receptor with greater affinity than xanomeline were discovered. Results indicate that persistent binding may arise not only from hydrophobic interactions but also from ionic interactions with a secondary M1 receptor binding site. Herein, a qualitative model that accounts for both binding scenarios is proposed and applied to understand the structural basis to wash-resistant binding and long-acting effects of xanomeline-based compounds.

PESTICIDAL SUBSTITUTED 1,2,5,-THIADIAZOLE DERIVATIVES

Insecticidal and acaricidal compositions comprising an insecticidally or acaricidally effective amount of a 1,2,5-thiadiazole of the formula (I); wherein R, Q and m are as defined in admixture with at least one agriculturally acceptable extender or adjuvant are disclosed. In addition, methods of controlling insects and acarids comprising applying said compositions to a locus of crops where control is desired are disclosed.

Palladium-catalyzed cross-coupling chemistry on 3-chloro-4-halo-1,2,5-thiadiazole

The present invention relates to 3-chloro-4-halo-1,2,5-thiadiazole compounds, a method of producing novel mono- and di-substituted-1,2,5-thiadiazoles therefrom, as well as mono- and di-substituted -1,2,5-thiadiazoles.

METHOD OF TREATING SCHIZOPHRENIA

The present invention relates to a novel method for treating a mammal suffering from or susceptible to schizophrenia and schizophreniform diseases by administering thiadiazole or oxadiazole compounds.

Heterocyclic compounds

The present invention relates to therapeutically active azacyclic compounds, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful as stimulants of the cognitive function of the forebrai

METHOD OF TREATING GASTROINTESTINAL MOTILITY DISORDERS

The present invention relates to a novel method for treating a mammal suffering from gastrointestinal motility disorders.