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

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

Uses

Used in Organic Synthesis:
3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is used as a key intermediate in organic synthesis for its ability to facilitate the construction of complex organic molecules. Its presence of multiple functional groups allows for a variety of chemical reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is employed as a starting material or a building block for the development of new pharmaceutical agents. Its structural attributes, particularly the presence of a formyl and methoxy group, make it a candidate for the design of novel compounds with potential therapeutic properties.
Used in Pharmaceutical Industry:
3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is used as a precursor in the pharmaceutical industry for the synthesis of indole-based drugs. Its structural similarity to naturally occurring indole compounds suggests that it may be involved in the development of medications targeting various therapeutic areas, including but not limited to central nervous system disorders, inflammation, and cancer.
Used in Chemical Research:
3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is utilized in chemical research as a model compound to study the reactivity and properties of indole derivatives. This helps in understanding the fundamental chemical behavior of such compounds, which can be instrumental in the advancement of synthetic methodologies and the discovery of new chemical entities with potential applications.

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

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

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].

Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids

We report here a concise, collective, and asymmetric total synthesis of sarpagine alkaloids and biogenetically related koumine alkaloids, which structurally feature a rigid cage scaffold, with L-tryptophan as the starting material. Two key bridged skeleton-forming reactions, namely tandem sequential oxidative cyclopropanol ring-opening cyclization and ketone α-allenylation, ensure concurrent assembly of the caged sarpagine scaffold and installation of requisite derivative handles. With a common caged intermediate as the branch point, by taking advantage of ketone and allene groups therein, total synthesis of five sarpagine alkaloids (affinisine, normacusine B, trinervine, Na-methyl-16-epipericyclivine, and vellosimine) with various substituents and three koumine alkaloids (koumine, koumimine, and N-demethylkoumine) with more complex cage scaffolds has been accomplished.

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.

A new route to α-carbolines based on 6π-electrocyclization of indole-3-alkenyl oximes

Indoles are converted into α-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolyl aldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 C under microwave irradiation undergo loss of the Boc-group, and 6π-electrocyclization to α-carbolines, following aromatization by loss of methanol (11 examples, 30-90% yield).

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.

Synthesis of homocarbonyltopsentine derivatives

Homocarbonyltopsentines I are known to exhibit interesting anti-inflammatory activity in vivo. In order to study the role of the heterocycles in the modulation of their activity, several analogues in which indoles were replaced either by substituted indol