59394-42-2

Usage

Derivative of indole

Indole is a heterocyclic aromatic compound commonly found in plant-based products. 1H-Indole-2-carboxylic acid, 5-bromo-3-phenyl-, ethyl ester is a derivative of indole, meaning it has been modified or altered in some way.

Ethyl ester group

The presence of the ethyl ester group in 1H-Indole-2-carboxylic acid, 5-bromo-3-phenyl-, ethyl ester makes it more soluble in organic solvents. This can be useful in the synthesis of other organic compounds.

Used as a reagent in organic synthesis

Because of its solubility and reactivity, 1H-Indole-2-carboxylic acid, 5-bromo-3-phenyl-, ethyl ester is often used as a reagent in organic synthesis, a process of creating new compounds from simpler molecules.

Potential pharmacological properties

The presence of the bromine and phenyl groups in its structure gives 1H-Indole-2-carboxylic acid, 5-bromo-3-phenyl-, ethyl ester potential pharmacological properties, making it of interest in the development of pharmaceuticals and agrochemicals.

Valuable tool for studying chemical reactions

The unique structure of 1H-Indole-2-carboxylic acid, 5-bromo-3-phenyl-, ethyl ester makes it a valuable tool for studying chemical reactions and mechanisms in organic chemistry. This can help scientists better understand how chemical reactions occur and how to design new compounds.

Upstream product

• 2028-85-5 (4-bromophenyl)diazonium chloride 
• 620-79-1 Ethyl 2-benzylacetoacetate 
• 15626-54-7 2-diazo-3-phenyl-propionic acid ethyl ester 
• 100-39-0 benzyl bromide 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 70070-31-4 5-bromo-3-phenyl-indole-2-carboxylic acid 
• 927690-41-3 (5-bromo-3-phenyl-1H-indol-2-yl)-(2-methoxymethyl-pyrrolidin-1-yl)-methanone 
• 1032291-27-2 C₁₆H₁₁BrN₄S 
• 1613695-88-7 C₂₂H₂₀N₂O₃ 
• 138653-82-4 1-(2-Amino-ethyl)-5-bromo-3-phenyl-1H-indole-2-carboxylic acid ethyl ester 
• 138653-68-6 8-Bromo-10-phenyl-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole 
• 105492-26-0 C₁₅H₁₃BrN₄O 
• 70070-27-8 5-Bromo-3-phenyl-1H-indole-2-carbonyl azide 
• 70070-34-7 ethyl 5-bromo-3-phenylindole-2-carbamate 
• 120608-04-0 5-Bromo-3-phenyl-1H-indole-2-carbonyl chloride 
• 70070-24-5 5-bromo-3-phenylindole-2-carboxyhydrazide 
• 138653-59-5 5-Bromo-1-cyanomethyl-3-phenyl-1H-indole-2-carboxylic acid ethyl ester 
• 226554-54-7 [5-(5-bromo-3-phenyl-1H-indol-2-yl)-2-thioxo-[1,3,4]oxadiazol-3-yl]-acetic acid ethyl ester 
• 226554-48-9 5-bromo-3-phenyl-2-(5'-thioxo-1',3',4'-oxadiazol-2'-yl)indole 

Relevant academic research and scientific papers

Identification of new 3-phenyl-1H-indole-2-carbohydrazide derivatives and their structure–activity relationships as potent tubulin inhibitors and anticancer agents: A combined in silico, in vitro and synthetic study

Virtual screening of commercially available molecular entities by using CDRUG, structure-based virtual screening, and similarity identified eight new derivatives of 3-phenyl-1H-indole-2-carbohydrazide with anti-proliferative activities. The molecules were tested experimentally for inhibition of tubulin polymerisation, which revealed furan-3-ylmethylene-3-phenyl-1H-indole-2-carbohydrazide (27a) as the most potent candidate. Molecule 27a was able to induce G2/M phase arrest in A549 cell line, similar to other tubulin inhibitors. Synthetic modifications of 27a were focussed on small substitutions on the furan ring, halogenation at R1 position and alteration of furyl connectivity. Derivatives 27b, 27d and 27i exhibited the strongest tubulin inhibition activities and were comparable to 27a. Bromine substitution at R1 position showed most prominent anticancer activities; derivatives 27b-27d displayed the strongest activities against HuCCA-1 cell line and were more potent than doxorubicin and the parent molecule 27a with IC50 values 50 = 0.34 μM), while 27d displayed stronger activity against A549 cell line (IC50 = 0.43 μM) compared to doxorubicin and 27a. Fluorine substitutions at the R1 position tended to show more modest anti-tubulin and anticancer activities, and change of 2-furyl to 3-furyl was tolerable. The new derivatives, thiophenyl 26, displayed the strongest activity against A549 cell line (IC50 = 0.19 μM), while 1-phenylethylidene 21b and 21c exhibited more modest anticancer activities with unclear mechanisms of action; 26 and 21c demonstrated G2/M phase arrest, but showed weak tubulin inhibitory properties. Molecular docking suggests the series inhibit tubulin at the colchicine site, in agreement with the experimental findings. The calculated molecular descriptors indicated that the molecules obey Lipinski's rule which suggests the molecules are drug-like structures.

Novel method for synthesis of aryl hydrazones from α-diazo esters: scope and limitations of nucleophiles

Aryl hydrazones, the precursor of Fischer indole synthesis, were easily obtained by nucleophilic addition of aryllithium reagents to diazo esters. The aryl hydrazones were converted into indoles in good yields by heating with thionyl chloride in alcohol.

Novel synthesis of 5-substituted-3-phenylindole-2-(1,2,4-triazole) derivatives

Various substituted 3-phenylindole 2-carboxylates (1a-c) were prepared according to the literature methods. These carboxylates (1a-c) on reaction with thiosemicarbazide yielded 5-substituted-3-phenylindol-2-(1,2,4-triazole-3- thione) (2a-c) on refluxing in pyridine for 8 h. The 5-substituted-3- phenylindole-2-[1,2,4-triazolo-3-thioacetic acid] (3a-c) were prepared from 5-substituted-3-phenyl indole-2-[1,2,4-triazole-3-thione] (2a-c) on reaction with an appropriate alkylating agent and sodium acetate in acetic acid. Further, (3a-c) were reacted with acetic anhydride to bring about a cyclocondensation reaction to yield 5-substituted-3-phenylindol-2-thiazolo(2,3-b)-triazole (4a-c). The 5-substituted-3-phenylindole-2-[1,2,4-triazolo-3-acetic acid] (3a-c) were reacted with o-phenylenediamino dihydrochloride in ethylene glycol to yield 5-substituted-3-phenylindole-1,2,4-triazolo-3′-yl-thiomethyl) benzimidazoles (5a-c). Copyright Taylor & Francis Group, LLC.

Novel approach to arylhydrazones, the precursor for Fischer indole synthesis, via diazo esters derived from α-amino acid esters

A novel method for synthesizing arylhydrazones, the precursor for Fischer indole synthesis, using aryllithium reagents and α-diazo esters that are easily obtained from α-amino acid esters, is described.

3-substituted indole antiproliferative angiogenesis inhibitors

3-Substituted indole carbohydrazides having the formula are useful for inhibiting angiogenesis and cell proliferation. Also disclosed are compositions which inhibit angiogenesis and cell proliferation and methods of inhibiting angiogenesis and cancer in a mammal.

3-substituted indole angiogenesis inhibitors

3-Substituted indole carbohydrazides having the formula are useful for inhibiting angiogenesis. Also disclosed are angiogenesis-inhibiting compositions and methods of inhibiting angiogenesis in a mammal.