155134-26-2

Usage

Molecular class

Indole derivatives

Structural features

Indole ring with a carboxylic acid group, phenylmethyl side chain, and methyl ester functional group

Common uses

Building block for the synthesis of various drugs and biologically active molecules in the pharmaceutical industry

Potential pharmacological activities

Possesses the potential to exhibit various pharmacological activities due to its structural features

Value in synthesis

Valuable intermediate in the fine chemical synthesis

Use in research and development

Used as a starting material in the design and synthesis of new chemical entities.

Upstream product

• 624-75-9 iodoacetonitrile 
• 78688-62-7 (E)-3-Phenylamino-pent-2-enedioic acid dimethyl ester 
• 3376-40-7 N-benzyl-N-phenylhydroxylamine 
• 922-67-8 propynoic acid methyl ester 
• 942-24-5 3-methoxycarbonylindole 
• 100-39-0 benzyl bromide 
• 1265902-10-0 methyl 3-(benzylamino)-2-(2-bromophenyl)acrylate 
• 620-05-3 iodomethylbenzene 
• 76464-99-8 N-benzyl-2-iodoaniline 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 324738-51-4 2′-N-benzylaminophenylacetylene 
• 122394-37-0 methyl α-formyl(o-bromophenyl)acetate 
• 100-46-9 benzylamine 

Downstream Products

• 163083-67-8 1-Benzyl-5-bromo-1H-indole-3-carboxylic acid methyl ester 
• 27018-76-4 1-benzylindole-3-carboxylic acid 
• 163083-64-5 1-Benzyl-6-methyl-1H-indole-3-carboxylic acid methyl ester 
• 163083-68-9 1-Benzyl-5-bromo-6-methylsulfanylmethyl-1H-indole-3-carboxylic acid methyl ester 
• 1334544-31-8 methyl 1-benzyl-2-iodoindole-3(1H)-carboxylate 
• 1334544-29-4 1-benzyl-2-iodoindole-3(1H)-carboxylic acid 
• 1334544-46-5 5-benzyl-3-pentylindolo[3,2-c]pyrane-1(5H)-one 
• 1334544-41-0 5-benzyl-3-(3-hydroxypropan-2-yl)pyrano[4,3-b]indol-1(5H)-one 
• 1334544-47-6 5-benzyl-3-(2-hydroxypropan-2-yl)indolo[3,2-c]pyrane-1(5H)-one 
• 1392495-71-4 C₅₂H₄₄N₁₀O₂S₂ 
• 1392495-72-5 C₅₀H₄₀N₁₀O₂S₂ 
• 1392495-73-6 C₅₀H₃₈Br₂N₁₀S₂ 
• 1392495-74-7 C₅₀H₃₈N₁₂O₄S₂ 
• 1392495-75-8 C₅₀H₃₈Br₂N₁₀S₂ 

Relevant academic research and scientific papers

Oxazole Synthesis by Sequential Asmic-Ester Condensations and Sulfanyl-Lithium Exchange-Trapping

Oxazoles are rapidly assembled through a sequential deprotonation-condensation of Asmic, anisylsulfanylmethylisocyanide, with esters followed by sulfanyl-lithium exchange-trapping. Deprotonating Asmic affords a metalated isocyanide that efficiently traps esters to afford oxazoles bearing a versatile C-4 anisylsulfanyl substituent. Interchange of the anisylsulfanyl substituent is readily achieved through a first-in-class sulfur-lithium exchange-electrophilic trapping sequence whose versatility is illustrated in the three-step synthesis of the bioactive natural product streptochlorin.

Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1

The ligand-sensing transcription factor nuclear receptor related 1 (Nurr1) evolves as an appealing target to treat neurodegenerative diseases. Despite its therapeutic potential observed in various rodent models, potent modulators for Nurr1 are lacking as pharmacological tools. Here, we report the structure-activity relationship and systematic optimization of indole-based inverse Nurr1 agonists. Optimized analogues decreased the receptor's intrinsic transcriptional activity by up to more than 90% and revealed preference for inhibiting Nurr1 monomer activity. In orthogonal cell-free settings, we detected displacement of NCoRs and disruption of the Nurr1 homodimer as molecular modes of action. The inverse Nurr1 agonists reduced the expression of Nurr1-regulated genes in T98G cells, and treatment with an inverse Nurr1 agonist mimicked the effect of Nurr1 silencing on interleukin-6 release from LPS-stimulated human astrocytes. The indole-based inverse Nurr1 agonists valuably extend the toolbox of Nurr1 modulators to further probe the role of Nurr1 in neuroinflammation, cancer, and beyond.

Synthesis method of 6-hydroisoindolo[2,1-alpha]indole compounds

The invention relates to a synthesis method of 6-hydroisoindolo[2,1-alpha]indole compounds, wherein the synthesis method comprises the steps: in an organic solvent system, synthesizing by taking a 1-aryl methylene indole compound as a basic raw material i

Synthesis of indoles via electron-catalyzed intramolecular C?N bond formation

A new protocol for the preparation of N-substituted indole-3-carboxylates has been developed. The key C?N bond formation occurs under transition-metal-free conditions employing a t-BuOK/DMF system without special initiators or additives. Across a number o

Synthesis and biological evaluation of novel indole derivatives containing sulfonamide scaffold as potential tubulin inhibitor

Microtubule-targeted drugs play a critical role in various types of cancer therapy worldwide. In our study, a series of novel indole derivatives containing a sulfonamide scaffold were designed, synthesized and biologically evaluated as potential tubulin p

Pd(ii)-catalyzed ligand controlled synthesis of methyl 1-benzyl-1H-indole- 3-carboxylates and bis(1-benzyl-1H-indol-3-yl)methanones

A simple change of ligand and solvent allows controlled, effective switching between cyclization-carbonylation and cyclization-carbonylation- cyclization-coupling (CCC-coupling) reactions of 2-alkynylanilines catalyzed by palladium(ii). The use of a [Pd(tfa)2(box)] catalyst in iPrOH afforded symmetrical ketones bearing two indoles in good yields; replacing the catalyst and solvent with Pd(tfa)2 and DMSO-MeOH led to the formation of methyl 1-benzyl-1H-indole-3-carboxylates in good yields. This journal is

A practical synthesis of indoles via a Pd-catalyzed C-N ring formation

A method for the synthesis of N-functionalized C2-/C3-substituted indoles via Pd-catalyzed C-N bond coupling of halo-aryl enamines is described. The general strategy utilizes a variety of amines and β-keto esters which are elaborated into halo-aryl enamin

Construction of indoloquinolinones via Pd(II)-catalyzed tandem CC/CN bond formation: Application to the total synthesis of isocryptolepine

Construction of indoloquinolinone skeleton via Pd-catalyzed tandem CC/CN bond formation has been achieved in moderate to good yields. The method was applied toward the total synthesis of the bioactive natural product isocryptolepine in good overall yields.

Microwave-assisted synthesis and biological activity of new Schiff bases derived from dimers of 4-amino-3-[3-(1-benzyl)indole]-5-thiomethyl-1,2,4- triazole

An expeditious method with microwave irradiation has been developed for synthesis of novel Schiff bases from dimers of 4-amino-3-[3-(1-benzyl)indole]-5- thiomethyl-1,2,4-triazole. Its distinct advantages are short reaction times and good conversion. The s

Regioselective copper-mediated synthesis of thieno[2,3- c ]pyrane-7-one, Indolo[2,3- c ]pyrane-1-one, and indolo[3,2- c ]pyrane-1-one

In the presence of copper(I) iodide, heteroaromatic Β-iodo-α, Β-unsaturated carboxylic acid systems opposed to terminal alkyne afford selectively 6-endo-dig cyclization products via a tandem coupling oxacyclization reaction.