Conversion of Isatins to Tryptanthrins, Heterocycles Endowed with a Myriad of Bioactivities

Amara, Rim Ben; Awad, Haçan; Chaker, Diana; Bentabed‐Ababsa, Ghenia; Lassagne, Frédéric; Erb, William; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Fajloun, Ziad; Vidal, Joëlle; Mongin, Florence

doi:10.1002/ejoc.201900352

Cited by 17 publications

(12 citation statements)

References 120 publications

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“…As 7-azaindole is present in bioactive molecules, some of the compounds synthesized have been screened for their biological properties [ 77 , 78 , 79 ]. The compounds 1a – c , 1e , 1f , 1h - j , 2k , 2l , 3a , 3g , 3g ′ and 5i were evaluated for their antimicrobial activity against bacteria and for their antifungal activity ( Table 5 ).…”

Section: Resultsmentioning

confidence: 99%

Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties

et al. 2021

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Five protocols were first compared for the copper-catalyzed C-N bond formation between 7-azaindole and aryl/heteroaryl iodides/bromides. The 1-arylated 7-azaindoles thus obtained were subjected to deprotometalation-iodolysis sequences using lithium 2,2,6,6-tetramethylpiperidide as the base and the corresponding zinc diamide as an in situ trap. The reactivity of the substrate was discussed in light of the calculated atomic charges and the pKa values. The behavior of the 1-arylated 7-azaindoles in direct iodination was then studied, and the results explained by considering the HOMO orbital coefficients and the atomic charges. Finally, some of the iodides generated, generally original, were involved in the N-arylation of indole. While crystallographic data were collected for fifteen of the synthesized compounds, biological properties (antimicrobial, antifungal and antioxidant activity) were evaluated for others.

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Section: Resultsmentioning

confidence: 99%

Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties

et al. 2021

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“…Tryptanthrin (73%) and aryl-substituted tryptanthrins (seven examples, 15–80% yield) were successfully obtained by using this approach. 23 Using the same solvent, with sodium hydride as base, and other iodine sources besides I 2 , such as 1,2-diiodoethane, our group reported the successful synthesis of tryptanthrin from isatin (56% yield) and also from indigo (83% yield). The use of two other dyes, Tyrian Purple and Tina Blue, also led to the formation of the corresponding di- and tetrabromotryptanthrin derivatives.…”

Section: New Approaches For the Synthesis Of Tryptanthrinmentioning

confidence: 99%

Tryptanthrin and Its Derivatives in Drug Discovery: Synthetic Insights

2022

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Tryptanthrin is a golden-yellow, naturally occurring alkaloid that can be obtained from multiple sources and through different synthetic methodologies. This tetracyclic compound displays several relevant biological activities. The potential of this tetracyclic alkaloid has been widely explored, and several researchers have focused their attention on expanding the variety of tryptanthrin derivatives by using a range of synthetic strategies. In this short review, we aim to address recent developments in the synthesis of the tryptanthrin core, as well as the development of new strategies employed by synthetic organic chemists to obtain novel tryptanthrin derivatives with potential biological activity, using different tools from the chemists’ toolbox, such as photocatalysis, solvent-free approaches, and multicomponent reactions.

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“…The reaction was carried out by the amide condensation reaction of indole-3-formaldehyde and isatoic anhydride compounds, or using indole-3-acetaldehyde and urea hydrogen peroxide (UHP) through Dakin oxidation, followed by intramolecular cyclization, to obtain tryptanthrin. Amara 11 used isatin as starting material and DMF as a solvent, and under the conditions of iodine and potassium hydroxide, with stirring at room temperature for 4 days, obtained tryptanthrin in 73% yield, using iodine as the reagent (Scheme 1 ). However, the reaction time is long, which is not suitable for industrial production.…”

Section: Table 1 Optimization Of Synthetic Conditions F...mentioning

confidence: 99%

A Novel and Practical Synthesis of Tryptanthrin

He¹,

chen²,

gao³

et al. 2022

Synthesis

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Thryptanthrin was synthesized through a two-step reaction of oxidation and condensation in a one-pot method, with isatin and sodium hypochlorite as starting materials. The influence of sodium hypochlorite, acetonitrile dosage, oxidation reaction temperature, and reaction time on the yield of the target product during the reaction was investigated. The following optimal reaction conditions were obtained: the ratio of n (isatin) to n (sodium hypochlorite) was 2:1, and the reaction time was 6–8 h at room temperature. The structure of tryptanthrin was confirmed by matching the IR, NMR, and Mass data with the literature report.The study shows that the chemical reaction route designed in this report is short, with high yield and purity of the target product. Its low production cost and simple operation method are expected to be applicable to industrial production.

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Conversion of Isatins to Tryptanthrins, Heterocycles Endowed with a Myriad of Bioactivities

Cited by 17 publications

References 120 publications

Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties

Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties

Tryptanthrin and Its Derivatives in Drug Discovery: Synthetic Insights

A Novel and Practical Synthesis of Tryptanthrin

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