Ca-mediated Nenitzescu synthesis of 5-hydroxyindoles

Teymori, Arezo; Sedaghat, Anna; Kobarfard, Farzad

doi:10.1007/s11696-022-02463-y

Cited by 2 publications

(6 citation statements)

References 25 publications

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“…The reaction was stirred for an additional hour, and then the mixture was cooled for 3-4 hours. The solid mixture was filtered off and then washed with CH 2 Cl 2 (10 mL) ( 25 ).…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Investigation of Cytotoxic Effects of 5-Hydroxyindole-3-Carboxylic Acid and Ester Derivatives as Potential Anti-breast Cancer Agents

et al. 2023

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: Breast cancer is a deadly disease with a high prevalence rate among females. Despite several treatments, scientists are still engaged in finding less invasive treatments for this disease. The cellular proliferation rate and cell viability survey are critical to assess the drug’s effect on both normal and malignant cell populations. Indole derivatives are promising candidates for their cytotoxic effect causing on breast cancer cells; however, they are less toxic on normal cells. This study synthesized 23 novel 5-hydroxyindole-3-carboxylic acids and related esters featuring various linear, cyclic, and primary aromatic amines. The MTT assay indicated the cytotoxicity of all acid and ester derivatives against the MCF-7 cells with no significant cytotoxicity on normal human dermal fibroblasts cells. Compound 5d, an ester derivative possessing a 4-methoxy group, was the most potent compound, with a half-maximal effective concentration of 4.7 µM. Compounds 5a, 5d, and 5l bearing ester group in their structure demonstrated cytotoxicity values < 10 µM against the MCF-7 cell line and were safe for advanced screening.

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“…The reaction was stirred for an additional hour, and then the mixture was cooled for 3-4 hours. The solid mixture was filtered off and then washed with CH 2 Cl 2 (10 mL) ( 25 ).…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Investigation of Cytotoxic Effects of 5-Hydroxyindole-3-Carboxylic Acid and Ester Derivatives as Potential Anti-breast Cancer Agents

et al. 2023

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“…All materials were used as received. 1 H-NMR (400 MHz) and 13 C-NMR (101 MHz) spectra were recorded in CDCl 3 with a Bruker Ascend 400 spectrometer (Bruker, Ettlingen, Germany) in CDCl 3 or DMSO d 6 solutions, and residual solvents peaks were used for calibration at 7.26 ppm and 2.50 ppm, respectively. Mass spectra were acquired using a Thermo Finnigan Q Exactive spectrometer (Thermo Fisher Scientific, Waltham, MA, USA) with an API-HESI source and a Fourier transform orbital trap (Orbitrap).…”

Section: Methodsmentioning

confidence: 99%

“…s., 1 H), 8.58 (dq, J = 4.88, 0.70 Hz, 1 H), 7.68 (td, J = 7.69, 1.82 Hz, 1 H), 7.31-7.27 (m, 1 H), 7.19 (dd, J = 7.26, 5.12 Hz, 1 H), 4.55-4.60 (m, 3 H), 4.13 (q, J = 7.14 Hz, 2 H), 1.94 (s, 3 H), 1.27 (t, J = 7.14 Hz, 3 H). 13 C NMR (101 MHz, CDCl 3 ), δ ppm 170. Ethyl 3-[(pyridin-2-ylmethyl)amino]but-2-enoate (1.032 g, 4.685 mmol, 1.00 eq) was dissolved in 25 mL of CPME.…”

Section: Synthesis Of Ethyl 3-[(pyridin-2-ylmethyl)amino]but-2-enoatementioning

confidence: 99%

“…1 H NMR (400 MHz, (CD 3 ) 2 SO), δ ppm 9.78 (s, 1 H, H25), 8.51-8.61 (m, 1 H, H19), 8.18-8.26 (m, 1 H, H8), 8.01-8.10 (m, 1 H, H7), 7.75 (s, 1 H, H4), 7.70 (td, J = 7.71, 1.78 Hz, 1 H, H17), 7.31-7.37 (m, 2 H, H18+H9), 7.27 (ddd, J = 7.20, 5.30, 1.00 Hz, 1 H, H16), 6.90 (d, J = 7.85 Hz, 1 H, H6), 5.92 (s, 2 H, H14), 4.35 (q, J = 7.11 Hz, 2 H, H23), 2.77 (s, 3 H, H21), 1.42 (t, J = 7.10 Hz, 3 H, H24). 13…”

Section: Synthesis Of Ethyl 3-[(pyridin-2-ylmethyl)amino]but-2-enoatementioning

confidence: 99%

“…Several advancements have been proposed to develop Nenitzescu synthesis, viz. the use of nitromethane as a solvent [11], as well as the application of Lewis acid catalysts [12,13] or enantioselective catalysts [14]. Herein, for the first time, we report on the synthesis of a 5-hydroxybenzoindole with a pyridyl substituent based on the slight modification of a procedure that we recently developed [15].…”

Section: Introductionmentioning

confidence: 99%

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