143724-34-9

Basic information

• Product Name: 1H-Indole, 5-(tributylstannyl)-
• Synonyms: 1H-Indole, 5-(tributylstannyl)-
• CAS NO: 143724-34-9
• Molecular Formula: C₂₀H₃₃NSn
• Molecular Weight: 406.19272
• Mol File: 143724-34-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indole, 5-(tributylstannyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 5-(tributylstannyl)-(143724-34-9)
• EPA Substance Registry System: 1H-Indole, 5-(tributylstannyl)-(143724-34-9)

Safety Data

• Hazardous Substances Data: 143724-34-9(Hazardous Substances Data)

Usage

Chemical structure

The compound consists of a central indole ring with a tributylstannyl group attached to the 5-position.

Indole ring

An important building block in organic synthesis, found in numerous natural products and pharmaceuticals.

Tributylstannyl group

A common functional group in organic chemistry, used for its ability to undergo cross-coupling reactions to form carbon-carbon bonds.

Reactivity

The compound is often used as an intermediate in the synthesis of diverse organic molecules and pharmaceuticals due to its versatility in forming new carbon-carbon bonds.

Upstream product

• 1461-22-9 tributyltin chloride 
• 10075-50-0 5-bromo-1H-indole 
• 813-19-4 bis(tri-n-butyltin) 

Downstream Products

• 1433194-56-9 ethyl 3-{4-[2-(5-cyclopropanoylindol-1-yl)ethoxy]phenyl}-2-ethoxypropionate 
• 1433194-57-0 ethyl 3-{4-[2-(5-cyclohexanoylindol-1-yl)ethoxy]phenyl}-2-ethoxypropionate 
• 1433194-63-8 C₂₅H₂₇NO₅ 
• 1433194-65-0 C₂₈H₃₃NO₅ 
• 1433194-69-4 ethyl 2-ethoxy-3-{4-[2-(5-{cyclopropyl-[E-methoxyimino]methyl}indol-1-yl)ethoxy]phenyl}propionate 
• 1439718-17-8 ethyl 2-ethoxy-3-{4-[2-(5-{cyclopropyl-[Z-methoxyimino]methyl}indol-1-yl)ethoxy]phenyl}propionate 
• 1433194-70-7 ethyl 2-ethoxy-3-{4-[2-(5-{cyclohexyl-[E-methoxyimino]methyl}indol-1-yl)ethoxy]phenyl}propionate 
• 1439719-04-6 ethyl 2-ethoxy-3-{4-[2-(5-{cyclohexyl-[Z-methoxyimino]methyl}indol-1-yl)ethoxy]phenyl}propionate 

Relevant articles and documents

Effect of Oxime Ether Incorporation in Acyl Indole Derivatives on PPAR Subtype Selectivity

Compounds that simultaneously activate peroxisome proliferator-activated receptor (PPAR) subtypes α and γ have the potential to effectively treat dyslipidemia and type2 diabetes (T2D) in a single pharmaceutically active molecule. The frequently observed side effects of selective PPARγ agonists, such as edema and weight gain, were expected to be overcome by using additive PPARα activity, leading to dual PPARα/γ agonists with balanced activity for both subtypes. Herein we report the discovery, synthesis, and optimization of a new series of α-ethoxyphenylpropionic acid bearing 5- or 6-substituted indoles. The incorporation of oxime ethers on the carbonyl portion of the benzoyl group can bring the PPARα/γ potency ratio equal to or slightly greater than one, as is the case for compounds 20c and 21a. Compound 20c shows high efficacy in an ob/ob mouse model of T2D and dyslipidemia, similar to that of rosiglitazone and tesaglitazar, but with a significant increase in body weight gain. In contrast, compound 21a, less potent as a dual PPARα/γ activator than 20c, showed an interesting pharmacological profile, as it elicits a decrease in body weight relative to reference compounds.