Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity

Daly, Seth M.; Hayden, Kathryn; Malik, Indranil; Porch, Nikki; Tang, Hong; Rogelj, Snezna; Frolova, Liliya V.; Lepthien, Katrina; Kornienko, Alexander; Magedov, I. V.

doi:10.1016/j.bmcl.2011.06.081

Cited by 44 publications

(16 citation statements)

References 20 publications

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“…Here, there remains an issue of regioselectivity when unsymmetric 1,4‐ketones are applied. Other reports of N−H‐carbazole synthesis are: b) the reaction of indole with two molecules of the same 1‐chloro‐4‐vinylbenzene under Pd/Cu catalysis followed by 6e‐cyclization affords 2,3‐bis(4‐chlorophenyl)‐9 H ‐carbazole in a 26 % combined yield; and c) the reaction of indole with 3‐methylpent‐1‐en‐4‐yn‐3‐ol catalyzed by a Ru complex produces 1,2‐dimethyl‐9 H ‐carbazole but in very low yield (15 %), and also with an issue of regioselectivity . In addition, Liang et al.…”

Section: Methodsmentioning

confidence: 99%

Carbazoles from the [4C+2C] Reaction of 2,3‐Allenols with Indoles

Guo

Huang

et al. 2016

Chemistry A European J

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A mild and efficient method using readily available 1-aryl-2,3-allenols and unprotected-N indoles, Au -catalyzed cyclization, and aromatization to afford the final [4C+2C] products, carbazoles 4, with an excellent selectivity, is reported. The reaction demonstrates excellent regioselectivity and allows the N-H unit to undergo reactivity unprotected. A mechanism involving a spiropolycyclic intermediate has been proposed and synthetic application is also demonstrated.

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Section: Methodsmentioning

confidence: 99%

Carbazoles from the [4C+2C] Reaction of 2,3‐Allenols with Indoles

Guo

Huang

et al. 2016

Chemistry A European J

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“…3–6 Heterocyclic compounds having a fused aromatic ring containing a pyrrole are known as “indoles” 5. This class of heterocycles is very interesting as it has applications in the fields of biology, medicine, 7–14 and organic photovoltaics 15,16 and as fluorescent dyes 17. Indole derivatives are well-known for antiviral activity and current clinical studies are evaluating these types of compounds 14.…”

Section: Introductionmentioning

confidence: 99%

“…Our spectroscopic findings are further supported by our theoretical calculations. The detailed synthetic procedure of this molecule can be found in a previous publication 7. A detailed account of the photoactivated antibacterial activities of this compound will be published in a separate paper.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Study of a Photoactive Antibacterial Agent: 2,3-Distyrylindole

et al. 2018

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Optical properties and fluorescence decay dynamics of a photoactive indole based antibacterial chromophore system, 2,3-distyrylindole (23DSI), were investigated using various spectroscopic characterization techniques. Experimental studies were done by utilizing steady-state UV-vis spectroscopy, steady-state fluorescence spectroscopy, time-resolved fluorescence upconversion spectroscopy, and time-correlated single-photon counting spectroscopy. Our studies show that the 23DSI molecule has a multiphoton absorption property as indicated by two- and three-photon absorption in the both the solution and the solid phases. The ultrafast time-resolved fluorescence upconversion studies show that this molecule undergoes a fast decay process with an average time constant of 34 ps, a single exponential decay, and an average fluorescence lifetime of 1 ns. The compound 23DSI did not show any signs of singlet oxygen production. The density functional theory (DFT) calculations showed that the 23DSI molecule has conjugated electron densities that are responsible for multiphoton absorption. The chlorine-substituted styryl groups, attached to the central indole ring facilitate the excellent electron delocalization within the molecule. This optimal electron delocalization, combined with the good electron conjugation in the 23DSI molecule is important for efficient multiphoton absorption and is in excellent agreement with experimental observations. Both the optical spectrum and emission spectrum using DFT calculations are also surprisingly well matched with the experimentally measured UV-vis spectrum and the emission spectrum, respectively. Combined experimental and theoretical studies suggest that excited electrons initially relax to the singlet state (S1) by internal conversion (IC) and subsequently relax back to their ground state by emitting absorbed energy as fluorescence emission. The outstanding multiphoton absorption capabilities of this 23DSI molecule support its potential application in both biological imaging and photodynamic inactivation (PDI).

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“…14 We showed that the metabolically labile azo group could be bioisosterically replaced by an ether or thioether functionalities leading to structures B , which were potent antibacterial agents as well. Unfortunately, these compounds were also found to inhibit the growth of human cervical cancer cells HeLa at comparable concentrations and this diminished our interest in pursuing them as novel antibacterials.…”

mentioning

confidence: 99%

Antiproliferative activity of 2,3-disubstituted indoles toward apoptosis-resistant cancers cells

Magedov

Lefranc

Frolova

et al. 2013

Bioorganic & Medicinal Chemistry Letters

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Many types of cancer, including glioma, melanoma, NSCLC, among others, are resistant to apoptosis induction and poorly responsive to current therapies with propaptotic agents. We describe a series of 2,3-disubstituted indoles, which display cytostatic rather than cytotoxic effects in cancer cells, and serve as a new chemical scaffold to develop anticancer agents capable of combating apoptosis-resistant cancers associated with dismal prognoses.

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Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity

Cited by 44 publications

References 20 publications

Carbazoles from the [4C+2C] Reaction of 2,3‐Allenols with Indoles

Carbazoles from the [4C+2C] Reaction of 2,3‐Allenols with Indoles

Spectroscopic Study of a Photoactive Antibacterial Agent: 2,3-Distyrylindole

Antiproliferative activity of 2,3-disubstituted indoles toward apoptosis-resistant cancers cells

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