Syntheses of spiro-oxindoles via KI/oxone-mediated oxidation/cyclization of homotryptamine and homotryptophol derivatives

zheng, Haohao; Chen, Xiangdong; Zuo, Jiayu; Ye, Jiang-Hai; Zhao, Chunsheng; Xu, Jun

doi:10.1016/j.tet.2023.133386

Cited by 4 publications

(1 citation statement)

References 38 publications

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“…[32] Similarly, ZnCl2, I2 and KI were reported as a catalyst in various reports on synthesizing new heterocycles. [33][34][35][36] In present work, we have synthesized bisindoles containing pyridine and pyrimidine derivatives incorporating green synthesis using thiamine hydrochloride as catalyst and water as solvent. Derivatives 5 a, 5 c, 5 d, 5 e, 5 f and 5 g are most potent having an IC 50 values of 2.48 � 0.39, 1.35 � 0.13, 3.36 � 0.53, 4.05 � 0.61, 1.91 � 0.28 and 8.12 � 0.91 μM respectively, against MCF-7 cells.…”

Section: Introductionmentioning

confidence: 99%

Development of Novel Pyridine and Pyrimidine Clubbed Bisindoles as Inhibitors of AKT Pathway

Poonacha,

Metri,

et al. 2024

ChemistrySelect

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Indoles and their derivatives have long been studied for their anticancer properties. Breast cancer has been treated using indole‐3‐carbinol, Indirubins, and many other naturally occurring indoles as well as their synthesized equivalents. It has been determined that the AKT pathway is a prospective target for therapeutic strategies in the treatment of breast cancer. The dysregulation of AKT pathway frequently promotes cell proliferation, survival, and resistance to apoptosis. We synthesized a novel group of bisindole clubbed pyridine and pyrimidine derivatives 5(a–l) using water as the solvent and thiamine hydrochloride as the catalyst. Compounds 5 a, 5 c, 5 d, 5 e, and 5 f are the most active against MCF‐7 cells, with an IC50 values of 2.48±0.39, 1.35±0.13, 3.36±0.53, 4.05±0.61 and 1.91±0.28 μM, respectively. Further, in silico docking of the active compound 5 c had the highest binding energy of −10.59 kcal/mol. Additionally, molecular dynanamics simulations were performed for better understanding the mode of interaction of ligand and protein. In conclusion, we have synthesized bisindoles using thiamine hydrochloride as a catalyst that target AKT pathway in breast cancer cells.

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Section: Introductionmentioning

confidence: 99%

Development of Novel Pyridine and Pyrimidine Clubbed Bisindoles as Inhibitors of AKT Pathway

Poonacha,

Metri,

et al. 2024

ChemistrySelect

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Hypervalent Iodine‐Mediated C3‐Trifluoropropionyloxylation of N‐Substituted Indoles

Tian,

Zhou,

Wang

et al. 2024

ChemistrySelect

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A metal‐free hypervalent iodine‐mediated C3‐trifluoropropionyloxylation of N‐substituted indoles was developed. (Bis‐trifluoropropanoate)iodobenzene was used as both the oxidant and fluorine source. The reaction was sensitive to the N‐protecting groups of the indoles. N‐acylated indoles provided 3‐trifluoropropionyloxylated indoles, while 3‐trifluoropropionyloxylated oxindoles were generated from indoles bearing N‐alkyl groups.

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Spirooxindoles: Recent report of green synthesis approach

Liandi,

Cahyana,

Alfariza

et al. 2024

Green Synthesis and Catalysis

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Syntheses of spiro-oxindoles via KI/oxone-mediated oxidation/cyclization of homotryptamine and homotryptophol derivatives

Cited by 4 publications

References 38 publications

Development of Novel Pyridine and Pyrimidine Clubbed Bisindoles as Inhibitors of AKT Pathway

Development of Novel Pyridine and Pyrimidine Clubbed Bisindoles as Inhibitors of AKT Pathway

Hypervalent Iodine‐Mediated C3‐Trifluoropropionyloxylation of N‐Substituted Indoles

Spirooxindoles: Recent report of green synthesis approach

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