93503-74-3Relevant academic research and scientific papers
A synthetic 2,3-diarylindole induces microtubule destabilization and G2/M cell cycle arrest in lung cancer cells
Thanaussavadate, Bongkotrat,Ngiwsara, Lukana,Lirdprapamongkol, Kriengsak,Svasti, Jisnuson,Chuawong, Pitak
supporting information, (2019/11/14)
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.
A synthetic 2,3-diarylindole induces cell death via apoptosis and autophagy in A549 lung cancer cells
Rukkijakan, Thanya,Ngiwsara, Lukana,Lirdprapamongkol, Kriengsak,Svasti, Jisnuson,Phetrak, Nared,Chuawong, Pitak
, p. 2119 - 2123 (2016/04/20)
A series of 2,3-diarylindoles were synthesized via the Larock heteroannulation, and evaluated for their anticancer activity against A549 lung cancer cells. The most potent compound, PCNT13 with IC50 = 5.17 μM, caused the induction of two modes of programmed cell death, apoptosis and autophagy.
Regioselectivity of Larock heteroannulation: A contribution from electronic properties of diarylacetylenes
Phetrak, Nared,Rukkijakan, Thanya,Sirijaraensre, Jakkapan,Prabpai, Samran,Kongsaeree, Palangpon,Klinchan, Chayada,Chuawong, Pitak
, p. 12703 - 12709 (2014/01/17)
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
Arcadi, Antonio,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Iazzetti, Antonia,Marinelli, Fabio
supporting information, p. 545 - 548 (2013/02/26)
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.
One-pot and regiospecific synthesis of 2,3-disubstituted indoles from 2-bromoanilides via consecutive palladium-catalyzed sonogashira coupling, amidopalladation, and reductive elimination
Lu, Bruce Z.,Wei, Han-Xun,Zhang, Yongda,Zhao, Wenyi,Dufour, Marine,Li, Guisheng,Farina, Vittorio,Senanayake, Chris H.
supporting information, p. 4558 - 4562 (2013/06/05)
A practical one-pot and regiospecific three-component process for the synthesis of 2,3-disubstituted indoles from 2-bromoanilides was developed via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.
A practical mild, one-pot, regiospecific synthesis of 2,3-disubstituted indoles via consecutive Sonogashira and Cacchi reactions
Lu, Bruce Z.,Zhao, Wenyi,Wei, Han-Xun,Dufour, Marine,Farina, Vittorio,Senanayake, Chris H.
, p. 3271 - 3274 (2007/10/03)
A practical one-pot, regiospecific three-component process for the synthesis of 2,3-disubstituted indoles was developed via consecutive Pd-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.
2,3-Disubstituted indoles through the palladium-catalyzed reaction of aryl chlorides with o-alkynyltrifluoroacetanilides
Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella
, p. 1301 - 1305 (2007/10/03)
2,3-Disubstituted indoles can be prepared in moderate to excellent yields by reacting readily available o-alkynyltrifluoroacetanilides with aryl chlorides in MeCN at 120°C in the presence of Pd2(dba)3 and Xphos.
Syntheses and complement inhibitory activities of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids
Bailey,DeGrazia,Alexander,Powles,Johnson,Patrick,Heerdt,Fairbain,Pruden
, p. 160 - 164 (2007/10/02)
The syntheses of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids are described. These compounds express potent in vitro inhibition of the human classical complement pathway, and qualitative SAR have been determined. Several of the in vitro active
