946077-08-3

Usage

Uses

Used in Research Applications:
(1-methyl-1H-indol-5-yl)-(3,4,5-trimethoxyphenyl)-methanone serves as a valuable compound in research settings, where it can be explored for its potential interactions with biological systems and its capacity to influence various biochemical processes. Its complex structure makes it an intriguing candidate for studies aimed at understanding its behavior and effects at the molecular level.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (1-methyl-1H-indol-5-yl)-(3,4,5-trimethoxyphenyl)-methanone may be employed as a starting point for the development of new drugs or as a component in the synthesis of medicinal compounds. Its unique structural features could potentially contribute to the creation of novel therapeutic agents, particularly if its biological activity is found to be beneficial in treating specific conditions or diseases.

Upstream product

• 133095-91-7 3,4,5-trimethoxyphenylmagnesium bromide 
• 10075-52-2 5-bromo-1-methyl-H-indole 
• 10075-50-0 5-bromo-1H-indole 
• 280563-07-7 1-methyl-5-iodoindole 
• 90923-75-4 1-methyl-1H-indole-5-carboxaldehyde 
• 671215-62-6 1-(benzenesulfonyl)-1H-indole-5-carbaldehyde 
• 1196-69-6 1H-indole-5-carboxaldehyde 
• 946077-16-3 (1H-indol-5-yl)(3,4,5-trimethoxyphenyl)methanone 
• 74-88-4 methyl iodide 
• 837392-62-8 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 

Downstream Products

• 1192108-55-6 1-methyl-5-[1-(3,4,5-trimethoxyphenyl)vinyl]-1H-indole 
• 1427690-75-2 C₂₁H₂₁NO₄ 
• 1427690-77-4 C₂₂H₂₁NO₅ 
• 1427690-81-0 C₂₁H₂₁NO₅ 
• 1427690-82-1 1-methyl-5-(1-(3,4,5-trimethoxyphenyl)vinyl)-3-vinyl-1H-indole 
• 1427690-83-2 C₂₁H₂₅NO₃ 
• 1427690-88-7 C₂₁H₂₀N₂O₃ 
• 1427690-89-8 1-methyl-5-[1-(3,4,5-trimethoxyphenyl)vinyl]-1H-indole-3-carbaldehydeoxime acetate 
• 1427690-93-4 C₂₁H₂₂N₂O₄ 
• 1427690-94-5 C₂₁H₂₃NO₄ 
• 1427690-73-0 1-methyl-5-(3,4,5-trimethoxybenzoyl)-1H-indole-3-carbaldehyde 

Relevant academic research and scientific papers

Synthesis, biological evaluation, and molecular docking analysis of phenstatin based indole linked chalcones as anticancer agents and tubulin polymerization inhibitors

A library of new phenstatin based indole linked chalcone compounds (9a-z and 9aa-ad) were designed and synthesized. Of these, compound 9a with 1-methyl, 2- and 3-methoxy substituents in the aromatic ring was efficacious against the human oral cancer cell

Kinetically Controlled, Highly Chemoselective Acylation of Functionalized Grignard Reagents with Amides by N?C Cleavage

The direct transition-metal-free acylation of amides with functionalized Grignard reagents by highly chemoselective N?C cleavage under kinetic control has been accomplished. The method offers rapid and convergent access to functionalized biaryl ketones through transient tetrahedral intermediates. The direct access to functionalized Grignard reagents by in situ halogen–magnesium exchange promoted by the versatile turbo-Grignard reagent (iPrMgCl?LiCl) permits excellent substrate scope with respect to both the amide and Grignard coupling partners. These reactions enable facile, operationally simple and chemoselective access to tetrahedral intermediates from amides under significantly milder conditions than chelation-controlled intermediates. This novel direct two-component coupling sets the stage for using amides as acylating reagents in an alternative paradigm to the metal-chelated approach, acyl metals and Weinreb amides.

Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic controlvs.kinetic control ofN,N-Boc2-amides

A highly efficient method for chemoselective synthesis of biaryl ketones by arylation of Weinreb amides (N-methoxy-N-methylamides) with functionalized Grignard reagents is reported. This protocol offers rapid entry to functionalized biaryl ketones after Mg/halide exchange with i-PrMgCl·LiCl under operationally-simple and practical reaction conditions. The scope of the method is highlighted in >40 examples, including bioactive compounds and pharmaceutical derivatives. Collectively, this transition-metal-free approach offers a major advantage over the recently established cross-coupling of amides by oxidative addition of N-C(O) bonds. Considering the utility of amide acylation reactions in modern synthesis, we expect that this method will be of broad interest.

New (3-(1: H -benzo [d] imidazol-2-yl))/(3-(3 H -imidazo[4,5- b] pyridin-2-yl))-(1 H -indol-5-yl)(3,4,5-trimethoxyphenyl)methanone conjugates as tubulin polymerization inhibitors

A series of new (3-(1H-benzo[d]imidazol-2-yl))/(3-(3H-imidazo[4,5-b]pyridin-2-yl))-(1H-indol-5-yl)(3,4,5-trimethoxyphenyl)methanone conjugates 4-6(a-i) were synthesized and evaluated for their antiproliferative activity on selected human cancer cell lines

Nickel-catalysed Suzuki-Miyaura coupling of amides

The Suzuki-Miyaura coupling has become one of the most important and prevalent methods for the construction of C-C bonds. Although palladium catalysis has historically dominated the field, the use of nickel catalysis has become increasingly widespread because of its unique ability to cleave carbon-heteroatom bonds that are unreactive towards other transition metals. We report the first nickel-catalysed Suzuki-Miyaura coupling of amides, which proceeds by an uncommon cleavage of the amide C-N bond after N-tert-butoxycarbonyl activation. The methodology is mild, functional-group tolerant and can be strategically employed in sequential transition-metal-catalysed cross-coupling sequences to unite heterocyclic fragments. These studies demonstrate that amides, despite classically considered inert substrates, can be harnessed as synthons for use in reactions that form C-C bonds through cleavage of the C-N bond using non-precious metal catalysis.

Endowing indole-based tubulin inhibitors with an anchor for derivatization: Highly potent 3-substituted indolephenstatins and indoleisocombretastatins

Colchicine site ligands with indole B rings are potent tubulin polymerization inhibitors. Structural modifications at the indole 3-position of 1-methyl-5-indolyl-based isocombretastatins (1,1-diarylethenes) and phenstatins endowed them with anchors for fu

Isocombretastatins A: 1,1-Diarylethenes as potent inhibitors of tubulin polymerization and cytotoxic compounds

Isocombretastatins A are 1,1-diarylethene isomers of combretastatins A. We have synthesized the isomers of combretastatin A-4, deoxycombretastatin A-4, 3-amino-deoxycombretastatin A-4 (AVE-8063), naphthylcombretastatin and the N-methyl- and N-ethyl-5-indo

Diarylmethyloxime and hydrazone derivatives with 5-indolyl moieties as potent inhibitors of tubulin polymerization

We describe the synthesis and biological evaluation of a series of diarylmethyloxime and diarylmethylhydrazone analogues that contain an indole ring and different modifications on the nitrogen of the bridge. Several compounds showed potent tubulin polymer

Novel potent antimitotic heterocyclic ketones: Synthesis, antiproliferative activity, and structure-activity relationships

We report the synthesis, antiproliferative activity, and SAR of novel heterocyclic ketones derived from carbazole sulfonamides. Most of the heterocyclic ketones showed strong cytotoxicities. (N-1-Methylindole-5-yl)-(3,4,5-trimethoxyphenyl)-methanone 8b gave the most potent cytotoxicity (9.2-26 nM) against seven human tumor cell lines. The mechanism of action of the heterocyclic ketones appears to involve targeting of tubulin, similar to that of CA-4 and different from the carbazole sulfonamides.

4- And 5-aroylindoles as novel classes of potent antitubulin agents

A novel series of 4- and 5-aroylindole derivatives was prepared and evaluated for antitumor activity. Several compounds showed excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 13,14,15, and 18, with IC50 v