Synthesis and cytotoxic activity of 3-phenyl-4-substituted-β-carbolines

Liu, Liu; Xu, Ying; Yang, Ze; Xiang, Jian Nan; Ma, Guangxu

doi:10.1016/j.cclet.2012.09.010

Cited by 8 publications

(5 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It suggested that an intermediate might be generated from iodine and 1a, and then reacted with 2a through chemical process to generate a new compound. 50,51 The conductivity of the solution decreased a little with the addition of substrates, and the oxidation peak potentials of curve e shifted positively as compared with curve f.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide

Chen

Niu

Shen

et al. 2018

J. Electrochem. Soc.

View full text Add to dashboard Cite

A novel electrochemical system for sulfenylation of indoles with disulfides to generate 3-sulfenylindoles via C-S bond formation mediated by potassium iodide at a low potential was developed. Iodine was electrogenerated from iodide ions at a graphite anode and showed a high catalytic activity for the electrochemical sulfenylation reactions. A variety of aromatic, heteroaromatic and aliphatic disulfides could react with 2-methlyindole to synthesize the corresponding 3-sulfenylindoles in good to excellent yields. In addition, protected and unprotected indoles with various groups, especially electron-donating groups, also performed well in the sulfenylation reactions. The transformation, which proceeded through the redox of iodine and the generation of intermediate 3-iodoindole, provided an efficient and environmentally benign protocol for the synthesis of 3-sulfenylindoles under mild conditions.

show abstract

Section: Resultsmentioning

confidence: 99%

“…However, intermediate 3-iodo-2-methyl-indole (4) was unstable and its isolated yield was only 15%. 50,51 No desired product 3aa was observed without electric current (Eq. 4).…”

Section: Scope Of Sulfenylation Of Indoles With Disulfidesmentioning

confidence: 99%

Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide

Chen

Niu

Shen

et al. 2018

J. Electrochem. Soc.

View full text Add to dashboard Cite

show abstract

“…The Pictet-Spengler reaction followed by a dehydrogenation reaction is the most widely used route to access βcarboline, [42] and most of β-carboline derivatives are synthesized through this method. In addition, β-carboline can be generated through the cyclization of terminal acetylene and azide groups catalyzed by transition metal, [43] or through photocatalytic cyclization of aniline pyridine. [16b]…”

Section: Synthetic Methods Of β-Carbolinementioning

confidence: 99%

“…Then, iodine-mediated coupling was performed to afford β-carboline 121, which was then hydrolyzed the protective group to give the product 123 (Scheme 20). [43] Furthermore, one-pot reaction was also successfully carried out in the synthesis of β-carboline. Indolealdehyde 124 and propargylamine 125 were reacted under alkaline medium instead of traditional metal catalyst to afford β-carboline 126 and γ-carboline 127 simultaneously in good yields (Scheme 21).…”

Section: Metal-free Cyclizationmentioning

confidence: 99%

Synthesis Strategies for α‐, β‐, γ‐ and δ‐Carbolines

Zhang

Wang

et al. 2021

Asian J Org Chem

View full text Add to dashboard Cite

Carbolines are widely present in various natural products and biological molecules. Numerous studies have shown the broad biological activities of these heterocyclic motifs, such as anticancer, antiviral, antibacterial, antiarrhythmic, and antidepressant activities, making carbolines very important in pharmaceutical applications. According to the different positions of nitrogen atom on the pyridine ring, carbolines are divided into four types, named α‐, β‐, γ‐ and δ‐carbolines. So far, numbers of strategies have been developed for each carboline, whereas the synthetic methods of four carbolines are different from each other. In this review, the synthetic strategy of four carbolines were summarized, providing the potential use of these scaffolds in therapeutic applications.

show abstract

“…Another study disclosed by Yu and co-workers reported the cyclization of azide using N -bromosuccinimide (NBS) in the presence of light, involving a radical mechanism (Scheme a, eq 2). Apart from these reports, Xu and co-workers explored the synthesis of 3-phenyl-4-substituted-β-carbolines via I 2 -mediated electrophilic cyclization of 3-alkynyl-2-azidomethylindoles. Song et al outlined the cascade reaction of benzyl azide and substituted indoles in the presence of triflic acid (TfOH) to furnish tetrahydro-5 H -indolo[3,2- c ]quinolines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of α-, β-, and γ-Carbolines via Intramolecular Cyclization of Azidomethyl(indolyl)acrylates Involving PIFA-BF₃·OEt₂/DBU-Mediated Cyclization as well as Thermolysis Approaches

Agneswaran,

Mohanakrishnan

2024

J. Org. Chem.

View full text Add to dashboard Cite

In this study, we present our findings on the synthesis of α-, β-, γ-carbolines via PIFA/BF 3 •OEt 2 -mediated intramolecular cyclization of isomeric azidomethyl(indolyl)acrylates. Alternately, 1,5,.0]dec-5-ene/1,8diazabicyclo(5.4.0)undec-7-ene (TBD/DBU)-mediated Michael addition followed by intramolecular cyclization of isomeric 2/3-(azidomethyl)indol-3/2-yl)acrylates also furnished the respective βand γ-carboline derivatives. Unexpectedly, the thermolysis of 2-(azidomethyl)-3-(indol-3-yl)acrylates led to the formation of ethyl 5-(2-(phenylsulfonamido)aryl)nicotinates along with γ-carbolines, via nitrene insertion followed by rearrangement and cyclization. The isomeric 2-(azidomethyl)-3-(indol-2-yl)acrylate upon thermolysis led to the expected δ-carboline. Thermal intramolecular nitrene insertion reaction could also be extended for accessing pyrido benzothiophene, pyrido thiophene, and quinoline.

show abstract

Synthesis and cytotoxic activity of 3-phenyl-4-substituted-β-carbolines

Cited by 8 publications

References 9 publications

Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide

Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide

Synthesis Strategies for α‐, β‐, γ‐ and δ‐Carbolines

Synthesis of α-, β-, and γ-Carbolines via Intramolecular Cyclization of Azidomethyl(indolyl)acrylates Involving PIFA-BF₃·OEt₂/DBU-Mediated Cyclization as well as Thermolysis Approaches

Contact Info

Product

Resources

About

Synthesis and cytotoxic activity of 3-phenyl-4-substituted-β-carbolines

Cited by 8 publications

References 9 publications

Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide

Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide

Synthesis Strategies for α‐, β‐, γ‐ and δ‐Carbolines

Synthesis of α-, β-, and γ-Carbolines via Intramolecular Cyclization of Azidomethyl(indolyl)acrylates Involving PIFA-BF3·OEt2/DBU-Mediated Cyclization as well as Thermolysis Approaches

Contact Info

Product

Resources

About

Synthesis of α-, β-, and γ-Carbolines via Intramolecular Cyclization of Azidomethyl(indolyl)acrylates Involving PIFA-BF₃·OEt₂/DBU-Mediated Cyclization as well as Thermolysis Approaches