847448-73-1

Basic information

• Product Name: 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;3-FORMYL-6-METHOXYINDOLE, N-BOC PROTECTED;6-METHOXYINDOLE-3-CARBOXALDEHYDE, N-BOC PROTECTED;1-Boc-3-formyl-6-methoxyindole;tert-butyl 3-formyl-6-methoxy-1H-indole-1-carboxylate;1H-INDOLE-1-CARBOXYLIC ACID, 3-FORMYL-6-METHOXY-, 1,1-DIMETHYLETHYL ESTER;6-Methoxy-1H-indole-3-carboxaldehyde,N-BOCprotected98%
• CAS NO: 847448-73-1
• Molecular Formula: C₁₅H₁₇NO₄
• Molecular Weight: 275.3
• Product Categories: API intermediates
• Mol File: 847448-73-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 415.487 °C at 760 mmHg
• Flash Point: 205.079 °C
• Appearance: /
• Density: 1.16 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.543
• CAS DataBase Reference: 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(847448-73-1)
• EPA Substance Registry System: 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(847448-73-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 847448-73-1(Hazardous Substances Data)

Usage

General Description

3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is a chemical compound with the molecular formula C15H17NO4. It is a tert-butyl ester derivative of 3-formyl-6-methoxyindole-1-carboxylic acid. 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is a yellow solid that is often used in organic synthesis and medicinal chemistry research. Its structure contains a formyl group, a methoxy group, and a carboxylic acid group, making it a versatile building block for the synthesis of various organic molecules. Additionally, 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER has potential pharmacological applications due to its structural similarity to naturally occurring indole compounds.

InChI:InChI=1/C15H17NO4/c1-15(2,3)20-14(18)16-8-10(9-17)12-6-5-11(19-4)7-13(12)16/h5-9H,1-4H3

Upstream product

• 3189-13-7 6-methoxylindole 
• 70555-46-3 6-methoxy-1H-indole-3-carbaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 914349-08-9 C₁₅H₁₉NO₄ 
• 1428968-60-8 1-(6-methoxy-1H-indol-3-yl)-2-((3-methoxyphenyl)amino)-2-phenylethanone 
• 1428968-59-5 1-(6-methoxy-1H-indol-3-yl)-2-((2-methoxypyridin-4-yl)amino)-2-phenylethanone 

Relevant articles and documents

The first synthesis of natural alkaloid capparine A

Substances containing a spirooxindole framework display important biological activities. Natural alkaloid capparine A [(S)-(?)-1] has an anti-inflammatory effect. In the present study, attention has been paid to the first total synthesis of natural capparine A [(S)-(?)-1]. Racemic capparine A [(±)-1] was synthesized by bromospirocyclization of 6-methoxy-1-Boc-brassinin with water, followed by oxidation of obtained spirobrassinol derivatives and removal of the Boc group. Synthesized racemic capparine A [(±)-1] was enantioresolved by derivatization with (1R,2S,5R)-menthyl chloroformate, chromatographic separation of diastereoisomers and the cleavage of the chiral auxiliary using sodium methoxide. Screening of anti-proliferative activity against human cancer cells revealed no anti-proliferative activity of the capparine A [(S)-(?)-1].

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.

VIRAL REPLICATION INHIBITORS

The present invention relates to a series of novel compounds, methods to prevent or treat viral infections in animals by using the novel compounds and to said novel compounds for use as a medicine, more preferably for use as a medicine to treat or prevent viral infections, particularly infections with RNA viruses, more particularly infections with viruses belonging to the family of the Flaviviridae, and yet more particularly infections with the Dengue virus. The present invention furthermore relates to pharmaceutical compositions or combination preparations of the novel compounds, to the compositions or preparations for use as a medicine, more preferably for the prevention or treatment of viral infections. The invention also relates to processes for preparation of the compounds.