Chemistry of Fluorinated Indoles

Muzalevskiy, Vasiliy M.; Serdyuk, Olga V.; Nenajdenko, Valentine G.

doi:10.1007/978-3-319-04346-3_3

Cited by 4 publications

(2 citation statements)

References 95 publications

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“…Alignment of the 1,5-diaryl-3-oxo-1,4-pentadienyl group at the primary site may be affected by the nature of the group attached to the heterocyclic nitrogen atom. [39][40][41] This group increased the cytotoxic potencies due to either extra binding with cellular constituents at the auxiliary binding site or by easing the interaction of the cytotoxin at the primary site. 42 On the contrary, the group attached on the nitrogen atom may result in potency reduction because of the repulsion between this bulky group and the auxiliary site therefore, preventing interaction between the 1,5-diaryl-3-oxo-1,4-pentadienyl moiety and the primary binding site.…”

Section: Rational and Chemistrymentioning

confidence: 99%

Discovery of new pyridine heterocyclic hybrids; design, synthesis, dynamic simulations, and in vitro and in vivo breast cancer biological assays

Abdelshaheed,

El Subbagh,

Tantawy

et al. 2023

RSC Adv.

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Section: Rational and Chemistrymentioning

confidence: 99%

Discovery of new pyridine heterocyclic hybrids; design, synthesis, dynamic simulations, and in vitro and in vivo breast cancer biological assays

Abdelshaheed,

El Subbagh,

Tantawy

et al. 2023

RSC Adv.

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“…Currently, an estimated 20 percent of pharmaceuticals prescribed or administered contain at least one fluorine atom. Their improved potential, such as enhanced affinity towards biological targets, increased metabolic stability, bioavailability and membrane permeability is due to the unique physiochemical and biological properties of organofluorine compounds [16][17][18] .…”

Section: Introductionmentioning

confidence: 99%

Environmentally benign, microwave-assisted chemoselective N-hydroxyalkylation of indoles with trifluoroacetaldehyde methyl hemiacetal

Schäfer¹,

Ellstrom²,

Sood³

et al. 2017

Arkivoc

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Dedicated to Prof. Kenneth Laali on the occasion of his 65 th birthday and life-long contributions to chemistryReceived 07-31-2017 Accepted 10-27-2017 Published on line 11-05-2017 AbstractThe chemoselective microwave-activated N-hydroxyalkylation of indoles using trifluoroacetaldehyde methylhemiacetal as the alkylating agent under mild conditions is described. The chemoselectivity of this reaction is determined by the solvent used. In dimethyl sulfoxide, the reaction occurs without the use of a strong base or a metal catalyst. This approach can be applied to a variety of different substituted indoles to obtain the corresponding N-alkylated products with high selectivity. The product 2,2,2-trifluoro-1-(1-H-indol-1-yl)ethanols combine two moieties of frequent pharmacological interest: the indole core and a CF 3 -group containing a hydroxyalkyl substituent.

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Photo‐Induced Difluoromethylation‐Cyclization of Indoles Using Tetrazole Sulfone Reagent Under Visible Light

Zhu,

Huang,

Zhou

et al. 2024

ChemistrySelect

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Polycyclic indoles are prevailed in natural products, pharmaceuticals and biologically active compounds. Herein is described photo‐induced difluoromethylation‐cyclization of N‐alkene tethered indoles to synthesis of tetrahydropyrido[1,2‐a]indole using 5‐((difluoromethyl)sulfonyl)‐1‐phenyl‐1H‐tetrazole as a CF2H radical source. This photochemical reaction tolerates an array of functional groups like ester, cyano, ketone, halide, ether, aldehyde and heteocycles. Mechanistic experiments indicated that the difluoromethyl radical and the single electron transfer were involved.

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Chemistry of Fluorinated Indoles

Cited by 4 publications

References 95 publications

Discovery of new pyridine heterocyclic hybrids; design, synthesis, dynamic simulations, and in vitro and in vivo breast cancer biological assays

Discovery of new pyridine heterocyclic hybrids; design, synthesis, dynamic simulations, and in vitro and in vivo breast cancer biological assays

Environmentally benign, microwave-assisted chemoselective N-hydroxyalkylation of indoles with trifluoroacetaldehyde methyl hemiacetal

Photo‐Induced Difluoromethylation‐Cyclization of Indoles Using Tetrazole Sulfone Reagent Under Visible Light

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