Synthesis and evaluation of biological activities of new sulfonamide and carbamate derivatives of 1H-pyrrolo[2,3-b]pyridine (7-azaindole)

Sudhamani, Hasti; Basha, Sakeenabi; Reddy, S. Muni Chandra; Sreedhar, B.; Adam, S.; Raju, C. Naga

doi:10.1007/s11164-016-2547-2

Cited by 12 publications

(10 citation statements)

References 28 publications

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“…At the same time, sulfonamides have attracted widespread attention from pesticide scientists because of their broad biological properties, such as antibacterial 25 and antiviral activities. 26 − 29 …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antiviral Bioactivity, and Mechanism of the Ferulic Acid Ester-Containing Sulfonamide Moiety

Ren

Yin

et al. 2020

ACS Omega

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Tobacco mosaic virus (TMV) has caused huge economic losses to tobacco, pepper, cucumber, and ornamental crops all over the world. However, few effective antiviral agents were developed and applied to control such plant disease. It is challenging to find an anti-TMV agent which is highly effective, less toxic, and environmentally friendly. In this work, a series of ferulic acid ester-containing sulfonamide moieties were designed and synthesized, and the antiviral activities of these compounds against TMV were evaluated. The anti-TMV biological activity test showed that the target compounds showed excellent anti-TMV activity in vitro and in vivo . In particular, compound 2 has excellent anti-TMV activity at 500 μg/mL, which is higher than that of the control drug ribavirin. The preliminary mechanism research results showed that compound 2 can obviously destroy the morphology of the virions to show excellent activity. The results show that the ferulic acid ester-containing sulfonamide moiety deserves further research and development.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antiviral Bioactivity, and Mechanism of the Ferulic Acid Ester-Containing Sulfonamide Moiety

Ren

Yin

et al. 2020

ACS Omega

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“…Furthermore, in vitro antitumor activities against human myelogenous leukemia K562 cells have been described for alkyl dialkylcarbamodithioates . These compounds are also known to be HIV‐I NCp7 inhibitors, antivirus agents, and nonvanilloid TRPV1 antagonists …”

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed C−S Coupling of Quaternary Ammonium Salts and Dialkylcarbamodithioic Acid Salts

et al. 2020

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An efficient synthesis of (chiral) alkyl dialkylcarbamodithioates via a CuI-catalyzed CÀ S cross-coupling reaction of (chiral) quaternary ammonium salts and (chiral) dialkylcarbamodithioic acid salts has been developed. CÀ S coupling products were obtained with extremely high ee values and yields, with enantioenriched arylmethyl trimethylammonium triflates affording the inverse absolute configuration.

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“…Experimental Procedure for Synthesis of Ethyl 1H-Pyrrolo-[2,3-B]pyridine-1-Carboxylate from 7-Azaindole. 40 In a round bottom flask, 7-azaindole (1 mmol) and tetrahydrofuran (5 mL) were taken. Then, the reaction mixture was cooled down to 0 °C and 2 mmol of 60% NaH was added and stirred for 1 h. After 1 h, 1.5 mmol of Ethyl chloroformate was added, and the reaction was continued for 2 h. After completion of the reaction, it was quenched with cold water and extracted with ethyl acetate.…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

Halogen Bond-Assisted Electron-Catalyzed Atom Economic Iodination of Heteroarenes at Room Temperature

2019

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A halogen bond-assisted electron-catalyzed iodination of heteroarenes has been developed for the first time under atom economic condition at room temperature. The iodination is successful with just 0.55 equiv of iodine and 0.50 equiv of peroxide. The kinetic study indicates that the reaction is elusive in the absence of a halogen bond between the substrate and iodine. The formation of a halogen bond, its importance in lowering the activation barrier for this reaction, the presence of radical intermediates in a reaction mixture, and the regioselectivity of the reaction have been demonstrated with several control experiments, spectroscopic analysis, and quantum chemical calculations. Allowing the formation of the halogen bond may offer a new strategy to generate the reactive radical intermediates and to enable the otherwise elusive electron-catalyzed reactions under mild reaction conditions.

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Synthesis and evaluation of biological activities of new sulfonamide and carbamate derivatives of 1H-pyrrolo[2,3-b]pyridine (7-azaindole)

Cited by 12 publications

References 28 publications

Design, Synthesis, Antiviral Bioactivity, and Mechanism of the Ferulic Acid Ester-Containing Sulfonamide Moiety

Design, Synthesis, Antiviral Bioactivity, and Mechanism of the Ferulic Acid Ester-Containing Sulfonamide Moiety

Copper‐Catalyzed C−S Coupling of Quaternary Ammonium Salts and Dialkylcarbamodithioic Acid Salts

Halogen Bond-Assisted Electron-Catalyzed Atom Economic Iodination of Heteroarenes at Room Temperature

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