The indole alkaloids from the roots of Isatidis Radix

Wang, Fa-Qin; Bi, Jingting; He, Lin; Chen, Jing; Zhang, Qiangzi; Hou, Xianbang; Xu, Hao

doi:10.1016/j.fitote.2021.104950

Cited by 11 publications

(6 citation statements)

References 16 publications

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“…Next, nonprotected indole was used as the substrate to reaction with N -(thioaryl)succinimide 2a ; the corresponding bis-arylthioindole 3j and monoarylthioindole 3k were isolated in 86 and 93% yields, respectively. Indole alkaloids are one of the main active chemical components in Radix Isatidis, among which indole-3-acetonitrile, 4-methoxyindolyl-3-acetonitrile, indolyl-3-acetic acid, and methyl indolyl-3-carboxylate show good anti-inflammatory activity. , It is possible to improve the pharmaceutical properties of these compounds by synthesizing thioindole derivatives through structural modification and transformation. However, only Tian’s group reported one example for the synthesis of 2-(2-(phenylthio)-1 H -indol-3-yl)acetonitrile from indole-3-acetonitrile with sulfonyl hydrazide through iodine-catalyzed C2 thioarylation .…”

Section: Resultsmentioning

confidence: 99%

A Method for the Synthesis of Thioindoles through Copper-Catalyzed C–S Bond Coupling Reaction

Huang,

Li,

Cui

et al. 2023

J. Org. Chem.

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We herein report the copper-catalyzed C−S bond coupling reaction of indoles with N-thiosuccinimides, resulting in moderate to excellent yields of mono-and bis-sulfenylated compounds such as arylthioindoles, alkylthioindoles, selenylated indoles, and cysteine-substituted indoles. Thioarylation and thioglycosylation at the C2 position of indole alkaloids in the Radix Isatidis were achieved via structural modification. The first total syntheses of isatindigotindolosides III and IV have been successfully carried out. The electrophilic sulfenyl bromides generated in situ can play an important role in the catalytic cycle.

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Section: Resultsmentioning

confidence: 99%

A Method for the Synthesis of Thioindoles through Copper-Catalyzed C–S Bond Coupling Reaction

Huang,

Li,

Cui

et al. 2023

J. Org. Chem.

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“…Compounds 212 to 214 are indole-γ-lactams and represent psammocindoles, a new class of indole alkaloids derived from three amino acids (isoleucine, leucine, and phenylalanine) [ 61 ]. Compounds 215 and 216 were isolated from the roots of Isatis indigotica , and they contain an indole acetonitrile motif ( Figure 10 ) [ 62 ].…”

Section: Isolation Of Novel Indole Alkaloidsmentioning

confidence: 99%

“…This hydrogen bonding possibly modulated the function of HA and produced the supposedly antiviral activities of compounds. Nevertheless, despite reporting compound 215 as an inhibitor of HA, no quantitative information is available [ 62 ].…”

Section: Bioactivities Of Novel Indole Alkaloidsmentioning

confidence: 99%

Indole-Containing Natural Products 2019–2022: Isolations, Reappraisals, Syntheses, and Biological Activities

et al. 2022

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Indole alkaloids represent a large subset of natural products, with more than 4100 known compounds. The majority of these alkaloids are biologically active, with some exhibiting excellent antitumor, antibacterial, antiviral, antifungal, and antiplasmodial activities. Consequently, the natural products of this class have attracted considerable attention as potential leads for novel therapeutics and are routinely isolated, characterized, and profiled to gauge their biological potential. However, data on indole alkaloids, their various structures, and bioactivities are complex due to their diverse sources, such as plants, fungi, bacteria, sponges, tunicates, and bryozoans; thus, isolation methods produce an incredible trove of information. The situation is exacerbated when synthetic derivatives, as well as their structures, bioactivities, and synthetic schemes, are considered. Thus, to make such data comprehensive and inform researchers about the current field’s state, this review summarizes recent reports on novel indole alkaloids. It deals with the isolation and characterization of 250 novel indole alkaloids, a reappraisal of previously reported compounds, and total syntheses of indole alkaloids. In addition, several syntheses and semi-syntheses of indole-containing derivatives and their bioactivities are reported between January 2019 and July 2022.

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“…4 In addition, the N–H group in the indole ring can also form hydrogen bonds with biological macromolecules such as proteins and nucleic acids, thereby affecting biological activity. 5 It is widely distributed in plants such as Isatidis radix , 6 Euodia rutaecarp a, 7 Rauvolfia serpentina , 8 and Catharanthus roseus . 9 Indole derivatives have a variety of pharmacological activities, 10 including anti-tumor, 11,12 anti-inflammatory, 13–15 anti-oxidant, 14–17 anti-Alzheimer's, 18 and anti-diabetic 19 activities; therefore, the indole ring plays an important role in the development of new agents.…”

Section: Introductionmentioning

confidence: 99%