850374-95-7

Basic information

• Product Name: 1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE
• Synonyms: 1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE;3-FORMYL-6-(METHOXYCARBONYL)-1H-INDOLE, N-BOC PROTECTED
• CAS NO: 850374-95-7
• Molecular Formula: C₁₆H₁₇NO₅
• Molecular Weight: 303.31
• Mol File: 850374-95-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 214 °C
• Boiling Point: 443.3°C at 760 mmHg
• Flash Point: 221.9°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 4.7E-08mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: 1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE(850374-95-7)
• EPA Substance Registry System: 1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE(850374-95-7)

Safety Data

• Hazardous Substances Data: 850374-95-7(Hazardous Substances Data)

Usage

General Description

1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE is a chemical compound with the molecular formula C20H20N2O6. It contains a tert-butyl group, a methyl group, and a formyl group attached to an indole ring, as well as two carboxylate groups. 1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE is a member of the indole class of chemicals, which are commonly found in plant-derived compounds and have a wide range of biological activities. The specific properties and uses of 1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE are not specified, but its structural features suggest that it may have applications in pharmaceuticals, agrochemicals, or materials science. Further research would be needed to fully understand this compound's potential uses and effects.

InChI:InChI=1/C16H17NO5/c1-16(2,3)22-15(20)17-8-11(9-18)12-6-5-10(7-13(12)17)14(19)21-4/h5-9H,1-4H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 133831-28-4 methyl 3-formyl-6-indolecarboxylate 

Downstream Products

• 1428969-28-1 3-(2-((3-methoxyphenyl)amino)-2-phenylacetyl)-1H-indole-6-carboxylic acid 
• 1428968-68-6 methyl 3-(2-((3-methoxyphenyl)amino)-2-phenylacetyl)-1H-indole-6-carboxylate 
• 1428968-62-0 methyl 3-(2-((2-methoxypyridin-4-yl)amino)-2-phenylacetyl)-1H-indole-6-carboxylate 

Relevant articles and documents

Structure-guided design, synthesis, and biological evaluation of (2-(1 H-Indol-3-yl)-1 H-imidazol-4-yl)(3,4,5-trimethoxyphenyl) methanone (ABI-231) analogues targeting the colchicine binding site in Tubulin

ABI-231 is a potent, orally bioavailable tubulin inhibitor that interacts with the colchicine binding site and is currently undergoing clinical trials for prostate cancer. Guided by the crystal structure of ABI-231 in complex with tubulin, we performed structure-activity relationship studies around the 3-indole moiety that led to the discovery of several potent ABI-231 analogues, most notably 10ab and 10bb. The crystal structures of 10ab and 10bb in complex with tubulin confirmed their improved molecular interactions to the colchicine site. In vitro, biological studies showed that new ABI-231 analogues disrupt tubulin polymerization, promote microtubule fragmentation, and inhibit cancer cell migration. In vivo, analogue 10bb not only significantly inhibits primary tumor growth and decreases tumor metastasis in melanoma xenograft models but also shows a significant ability to overcome paclitaxel resistance in a taxane-resistant PC-3/TxR model. In addition, pharmacological screening suggested that 10bb has a low risk of potential off-target function.