1586-46-5

Basic information

• Product Name: 4-[2-(1H-indol-3-yl)ethenyl]quinoline
• Synonyms: 4-[2-(1H-indol-3-yl)ethenyl]quinoline
• CAS NO: 1586-46-5
• Molecular Formula: C19H14N2
• Molecular Weight: 270.3279
• Mol File: 1586-46-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 511.5 °C at 760 mmHg
• Flash Point: 232.5 °C
• Appearance: /
• Density: 1.272g/cm³
• Vapor Pressure: 4.5E-10mmHg at 25°C
• Refractive Index: 1.812
• CAS DataBase Reference: 4-[2-(1H-indol-3-yl)ethenyl]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[2-(1H-indol-3-yl)ethenyl]quinoline(1586-46-5)
• EPA Substance Registry System: 4-[2-(1H-indol-3-yl)ethenyl]quinoline(1586-46-5)

Safety Data

• Hazardous Substances Data: 1586-46-5(Hazardous Substances Data)

Usage

General Description

4-[2-(1H-indol-3-yl)ethenyl]quinoline, also known as IQ1, is a chemical compound with a molecular formula C20H14N2. It belongs to the class of quinoline compounds and contains an indole group and a quinoline ring. IQ1 has been studied for its potential therapeutic applications, particularly in cancer treatment. It has shown promising anti-cancer properties in preclinical experiments, including inhibiting the growth of certain types of cancer cells. Additionally, IQ1 has been investigated for its potential to modulate the activity of a protein called BAF complexes, which are involved in gene expression and DNA repair processes. Overall, 4-[2-(1H-indol-3-yl)ethenyl]quinoline is a compound of interest for its potential medicinal and biological applications.

InChI:InChI=1/C19H14N2/c1-3-7-18-16(5-1)14(11-12-20-18)9-10-15-13-21-19-8-4-2-6-17(15)19/h1-13,21H

Upstream product

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 487-89-8 Indole-3-carboxaldehyde 

Relevant articles and documents

Small molecule IVQ, as a prodrug of gluconeogenesis inhibitor QVO, efficiently ameliorates glucose homeostasis in type 2 diabetic mice

Gluconeogenesis is a major source of hyperglycemia in patients with type 2 diabetes mellitus (T2DM), thus targeting gluconeogenesis to suppress glucose production is a promising strategy for anti-T2DM drug discovery. In our preliminary in vitro studies, we found that a small-molecule (E)-3-(2-(quinoline-4-yl)vinyl)-1H-indol-6-ol (QVO) inhibited the hepatic glucose production (HGP) in primary hepatocytes. We further revealed that QVO suppressed hepatic gluconeogenesis involving calmodulin-dependent protein kinase kinase β- and liver kinase B1-adenosine monophosphate-activated protein kinase (AMPK) pathways as well as AMPK-independent mitochondrial function-related signaling pathway. To evaluate QVO’s anti-T2DM activity in vivo, which was impeded by the complicated synthesis route of QVO with a low yield, we designed and synthesized 4-[2-(1H-indol-3-yl)vinyl]quinoline (IVQ) as a prodrug with easier synthesis route and higher yield. IVQ did not inhibit the HGP in primary hepatocytes in vitro. Pharmacokinetic studies demonstrated that IVQ was quickly converted to QVO in mice and rats following administration. In both db/db and ob/ob mice, oral administration of IVQ hydrochloride (IVQ-HCl) (23 and 46 mg/kg every day, for 5 weeks) ameliorated hyperglycemia, and suppressed hepatic gluconeogenesis and activated AMPK signaling pathway in the liver tissues. Furthermore, IVQ caused neither cardiovascular system dysfunction nor genotoxicity. The good druggability of IVQ has highlighted its potential in the treatment of T2DM and the prodrug design for anti-T2DM drug development.