93503-74-3

Basic information

• Product Name: Benzoic acid, 4-(2-phenyl-1H-indol-3-yl)-, methyl ester
• CAS NO: 93503-74-3
• Molecular Formula: C22H17NO2
• Molecular Weight: 327.382
• Mol File: 93503-74-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-(2-phenyl-1H-indol-3-yl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-(2-phenyl-1H-indol-3-yl)-, methyl ester(93503-74-3)
• EPA Substance Registry System: Benzoic acid, 4-(2-phenyl-1H-indol-3-yl)-, methyl ester(93503-74-3)

Safety Data

• Hazardous Substances Data: 93503-74-3(Hazardous Substances Data)

Upstream product

• 93503-50-5 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylic acid 
• 874-61-3 4-oxocyclohexanecarboxylic acid 
• 948-65-2 2-phenyl-indole 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 143360-89-8 o-(phenylethynyl)trifluoroacetanilide 
• 2905-65-9 methyl 3-chlorobenzoate 
• 93503-51-6 methyl 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylate 
• 615-43-0 2-iodophenylamine 
• 42497-80-3 methyl 4-(phenylethynyl)benzoate 
• 29822-79-5 4-(2-phenylethynyl)benzonitrile 
• 536-74-3 phenylacetylene 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 2727-71-1 N-(2-bromophenyl)-2,2,2-trifluoroacetamide 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 

Downstream Products

• 93503-73-2 4-(2-phenyl-1H-indol-3-yl)benzoic acid 

Relevant articles and documents

A synthetic 2,3-diarylindole induces microtubule destabilization and G2/M cell cycle arrest in lung cancer cells

The anticancer potential of a synthetic 2,3-diarylindole (PCNT13) has been demonstrated in A549 lung cancer cells by inducing both apoptosis and autophagic cell death. In this report, we designed to connect a fluorophore to the compound via a hydrophilic linker for monitoring intracellular localization. The best position for linker attachment was identified from cytotoxicity and effect on cell morphology of newly synthesized PCNT13 derivatives bearing hydrophilic linker. Cytotoxicity and effect on cell morphology related to the parental compound were used to identify the optimum position for linker attachment in the PCNT13 chemical structure. The fluorophore-PCNT13 conjugate was found to localize in the cytoplasm. Microtubules were found to be one of the cytosolic target proteins of PCNT13, as the compound could inhibit tubulin polymerization in vitro. A molecular docking study revealed that PCNT13 binds at the colchicine binding site on the α/β-tubulin heterodimer. The effect of PCNT13 on microtubule dynamics caused cell cycle arrest in the G2/M phase as analyzed by flow cytometric analysis.

Regioselectivity of Larock heteroannulation: A contribution from electronic properties of diarylacetylenes

A series of 2,3-diarylindoles were synthesized from 2-iodoaniline and unsymmetrical diarylacetylenes using the Larock heteroannulation. Diarylacetylenes bearing electron-withdrawing substituents lead to 2,3-diarylindoles with substituted phenyl moieties at the 2-position as major products, while those with electron-donating groups preferably yield indole products with substituted phenyl moieties at the 3-position. The regioisomeric product ratios exhibit a clear correlation with Hammett σp values. DFT calculations reveal the origin of this effect, displaying smaller activation energy barriers for those pathways leading to the major regioisomer.

2-Substituted 3-arylindoles through palladium-catalyzed arylative cyclization of 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions

Free NH 2-substituted 3-arylindoles have been prepared usually in good to high yields through the palladium-catalyzed reaction of readily available 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions. The reaction tolerates a variety of useful functional groups both in the arylboronic acid and in the alkyne, including chloro, formyl, and ester groups.