404888-01-3

Basic information

• Product Name: 4-BENZYLOXY-1-BOC-3-INDOLECARBALDEHYDE
• Synonyms: 4-BENZYLOXY-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;4-BENZYLOXY-3-FORMYLINDOLE, N-BOC PROTECTED;4-BENZYLOXY-1-BOC-3-INDOLECARBALDEHYDE;4-BENZYLOXYINDOLE-3-CARBOXALDEHYDE, N-BOC PROTECTED;4-Benzyloxyindole-3-carboxaldehyde, N-BOC protected 98%;4-Benzyloxy-3-formylindole-1-carboxylic;4-Benzyloxy-1H-indole-3-carboxaldehyde, N-BOC protected 98%;4-Benzyloxy-1H-indole-3-carboxaldehyde, N-BOC protected
• CAS NO: 404888-01-3
• Molecular Formula: C21H21NO4
• Molecular Weight: 351.4
• EINECS: 604-604-1
• Mol File: 404888-01-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 511.715 °C at 760 mmHg
• Flash Point: 263.276 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: 4-BENZYLOXY-1-BOC-3-INDOLECARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXY-1-BOC-3-INDOLECARBALDEHYDE(404888-01-3)
• EPA Substance Registry System: 4-BENZYLOXY-1-BOC-3-INDOLECARBALDEHYDE(404888-01-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 404888-01-3(Hazardous Substances Data)

Usage

General Description

4-BENZYLOXY-1-BOC-3-INDOLECARBALDEHYDE is a chemical compound that belongs to the class of indole derivatives. It is commonly used as an intermediate in organic synthesis, particularly in the pharmaceutical industry. The compound is known for its diverse range of applications, including its role as a building block for the synthesis of various biologically active molecules. With a molecular structure consisting of a benzyl ether group, a BOC-protected amine, and an indolecarbaldehyde moiety, 4-BENZYLOXY-1-BOC-3-INDOLECARBALDEHYDE offers a versatile platform for the creation of novel chemical compounds with potential pharmacological properties.

InChI:InChI=1/C21H21NO4/c1-21(2,3)26-20(24)22-12-16(13-23)19-17(22)10-7-11-18(19)25-14-15-8-5-4-6-9-15/h4-13H,14H2,1-3H3

Upstream product

• 7042-71-9 4-benzyloxyindole-3-carbaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 81779-27-3 4-Hydroxyindole-3-carbaldehyde 
• 100-39-0 benzyl bromide 
• 404888-00-2 3-Formyl-4-hydroxyindole-1-carboxylic acid tert-butyl ester 

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.