6266-99-5

Basic information

• Product Name: SIB 1893
• Synonyms: SIB 1893;2-METHYL-6-(2-PHENYLETHENYL)PYRIDINE;(E)-2-METHYL-6-(2-PHENYLETHYL)-PYRIDINE;(E)-2-METHYL-6-STYRYL-PYRIDINE;2-Methyl-6-[(E)-2-phenylethenyl]pyridine;NSC 36665
• CAS NO: 6266-99-5
• Molecular Formula: C14H13N
• Molecular Weight: 195.26
• Product Categories: Glutamate receptor
• Mol File: 6266-99-5.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 307.3 °C at 760 mmHg
• Flash Point: 128.8 °C
• Appearance: /solid
• Density: 1.072 g/cm³
• Vapor Pressure: 0.00133mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: 2-8°C
• Solubility: DMSO: 18 mg/mL
• CAS DataBase Reference: SIB 1893(CAS DataBase Reference)
• NIST Chemistry Reference: SIB 1893(6266-99-5)
• EPA Substance Registry System: SIB 1893(6266-99-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 6266-99-5(Hazardous Substances Data)

Usage

Description

SIB 1893 is a pharmaceutical compound that functions as a selective antagonist of the metabotropic glutamate receptor 5 (mGluR-5) and also acts as a positive allosteric modulator of human metabotropic mGlu4. It is known for its potential therapeutic effects in various neurological conditions.

Uses

Used in Pharmaceutical Industry:
SIB 1893 is used as an anticonvulsant agent for the treatment of epilepsy and other seizure disorders. Its mechanism of action involves modulating the activity of mGluR-5 and mGlu4 receptors, which can help reduce the frequency and severity of seizures.
Additionally, due to its role as a positive allosteric modulator of mGlu4, SIB 1893 may also have potential applications in the treatment of other neurological conditions, such as Parkinson's disease, Alzheimer's disease, and chronic pain, by enhancing the function of the mGlu4 receptor and promoting neuroprotection and synaptic plasticity. However, further research is needed to fully understand the extent of its therapeutic potential in these areas.

Biological Activity

A highly selective non-competitive antagonist for the metabotropic glutamate mGlu 5 receptor subtype; displays an IC 50 value of 0.3 μ M? at hmGlu 5 , compared with > 100 μ M at hmGlu 1b , hmGlu 2 , hmGlu 6 , hmGlu 7 and hmGlu 8 . Centrally active upon systemic administration in vivo . Positive allosteric modulator at mGlu 4 receptors.

InChI:InChI=1/C14H13N/c1-12-6-5-9-14(15-12)11-10-13-7-3-2-4-8-13/h2-11H,1H3/b11-10+

Upstream product

• 108-48-5 2,6-dimethylpyridine 
• 100-52-7 benzaldehyde 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 109-06-8 α-picoline 
• 6738-06-3 phenylethynylmagnesium bromide 
• 51608-60-7 phenyl N-tosyl imine 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 96206-92-7 2-methyl-6-(phenylethynyl)pyridine 
• 1122-71-0 2-(Hydroxymethyl)-6-methylpyridine 
• 3112-88-7 Benzyl phenyl sulfone 
• 5315-25-3 2-bromo-6-methylpyridine 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 103-64-0 bromostyrene 
• 100-46-9 benzylamine 

Relevant articles and documents

Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase Inspired Catalyst

We explored the bioinspired o-quinone cofactor catalyzed aerobic primary amine dehydrogenation for a cascade olefination reaction with nine different methyl N-heteroarenes, including pyrimidines, pyrazines, pyridines, quinolines, quinoxolines, benzimidazoles, benzoxazoles, benzthiazoles, and triazines. An o-quinone catalyst phd (1,10-phenanthroline-5,6-dione) combined with a Br?nsted acid catalyzed the reaction. N-Heteroaryl stilbenoids were synthesized in high yields and (E)-selectivities under mild conditions using oxygen (1 atm) as the sole oxidant without needing transition-metal salt, ligand, stoichiometric base, or oxidant.

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.

C(sp3)-H functionalization of methyl azaarenes: a calcium-catalyzed facile synthesis of (E)-2-styryl azaarenes and 2-aryl-1,3-bisazaarenes

Alkaline earth (Ca2+) catalyzed sp3 C-H functionalization of methyl azaarenes for the synthesis of biologically important (E)-2-styryl azaarenes, 2-aryl-1,3-bisazaarenes and 3,3-bisazaarenyl indolinones has been described. Initially methyl azaarenes react with aryl aldehydes to give β-hydroxy derivatives, which undergo Ca(II) catalyzed thermodynamic elimination to give the styryl azaarenes in a single step. Similarly it may undergo SN1 reaction to give 2-aryl-1,3-bisazaarenes and 3,3-bisazaarenyl indolinones (if isatin used as the electrophile). This green synthetic methodology enjoys the simple reaction procedures, solvent free conditions, step economy, substrate diversity and high yields of the products in short time.