Synthesis and free radical scavenging activity of 2-alkyl/arylchalcogenyl-N-(4-aryl-1,3-thiazol-2-yl)acetamide compounds

Wolf, Lucas; Quoos, Natália; Mayer, João Cândido Pilar; Souza, Diego de; Sauer, André C.; Meichtry, Luana Barreto; Bortolotto, Vandreza Cardoso; Prigol, Marina; Rodrigues, Oscar E. D.; Dornelles, Luciano

doi:10.1016/j.tetlet.2016.01.079

Cited by 10 publications

(3 citation statements)

References 30 publications

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“…The ability of an extract to scavenge protonated radicals is an important property that relates to its antioxidant ability (Wolf et al 2016). ABTS• + is a protonated radical that was used to assess the antioxidant property of L. leonurus.…”

Section: Abts Radical Scavenging Activitymentioning

confidence: 99%

Chemical constituents, antioxidant and cytotoxicity properties of Leonotis leonurus used in the folklore management of neurological disorders in the Eastern Cape, South Africa

et al. 2020

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In the present study, we evaluated the phytochemical compounds and antioxidant properties of chloroform, ethanol and acetone extracts for leaves and flowers of Leonutus leonurus (L. leonurus) alongside with their cytotoxic effects on human cervical carcinoma (HeLa) cell lines. The phytochemical compounds present in the leaves and flowers of L. leonurus included; phenolics, flavonoids and alkaloids. Their radicals scavenging effects against 2, 2-diphenyl-1-picrylhydrazyl [DPPH] 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulphonate) [ABTS• + ], hydrogen peroxide, nitric oxide as well as metal chelating activities showed dose-dependent activities. Gas chromatography-mass spectrometry (GCMS) analyses revealed the presence of important bioactive compounds, which are associated with antioxidant; and the extracts exhibited toxicity effect against HeLa cells. The findings from this study divulge extracts of L. leonurus as prospective sources of antioxidant and anticancer agents; and hence, further study on their neuroprotective potentials becomes imperative.

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Section: Abts Radical Scavenging Activitymentioning

confidence: 99%

Chemical constituents, antioxidant and cytotoxicity properties of Leonotis leonurus used in the folklore management of neurological disorders in the Eastern Cape, South Africa

et al. 2020

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“…Subsequent acylation of the 2-aminothiazoles (2a-2e) with chloroacetyl chloride in the presence of triethylamine afforded 2-(2-chloroacetamido) thiazoles in good yield (3a-3e), which were further reacted with piperazine in the presence of TEA and 1,4-dioxane to afford the key intermediates, N-(substituted thiazol-2-yl)-2-(piperazine-1-yl)acetamides (4a-4e), in good yields. 17,18 The 1 H NMR spectra of the intermediates (3a-3e) indicated the presence of signals at δ 3-4 ppm, due to CH 2 of the chloroacetamide group, and at δ 7-8 ppm assigned to the 2-amino-4-phenylthiazole ring along with their molecular weight determination from mass spectra which confirmed the structures of the N-(substituted thiazol-2-yl)-2-(piperazine-1-yl)acetamides (4a-4e). Finally, the Mannich reaction was employed to treat bergenin (5) with the as-prepared substituted arylthiazolylpiperazines (4a-4e) in the presence of formaldehyde in DMSO to afford the desired final products (5a-e).…”

Section: Chemistrymentioning

confidence: 99%

Piperazine tethered bergenin heterocyclic hybrids: design, synthesis, anticancer activity, and molecular docking studies

et al. 2022

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“…On the other hand, required 1-aryl-2-bromoethanones 15 were prepared from the reaction of arylethanones 14 with N-bromo-succinimide (NBS) in acetonitrile using p -toluenesulfonic acid (PTSA) as a catalyst in good yields (Scheme 1). 25 Finally, the reaction of β- carboline 13 and 1-aryl-2-bromoethanone 15 was performed in refluxing ethanol. After refluxing the reaction contents for 20 h, we isolated the β- carboline salt 16 only in moderate yield (55%).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and in vitro cytotoxicity studies of novel β -carbolinium bromides

Reddy

Mishra

Tantak

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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A series of novel β-carbolinium bromides has been synthesized from easily accessible β-carbolines and 1-aryl-2-bromoethanones. The newly synthesized compounds were evaluated for their in vitro anticancer activity. Among the synthesized derivatives, compounds 16l, 16o and 16s exhibited potent anticancer activity with IC values of <10μM against tested cancer cell lines. The most potent analogue 16l was broadly active against all the tested cancer cell lines (IC=3.16-7.93μM). In order to test the mechanism of cell death, we exposed castration resistant prostate cancer cell line (C4-2) to compounds 16l and 16s, which resulted in increased levels of cleaved PARP1 and AO/EB staining, indicating that β-carbolinium salts induce apoptosis in these cells. Additionally, the most potent β-carbolines 16l and 16s were found to inhibit tubulin polymerization.

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Synthesis and free radical scavenging activity of 2-alkyl/arylchalcogenyl-N-(4-aryl-1,3-thiazol-2-yl)acetamide compounds

Cited by 10 publications

References 30 publications

Chemical constituents, antioxidant and cytotoxicity properties of Leonotis leonurus used in the folklore management of neurological disorders in the Eastern Cape, South Africa

Chemical constituents, antioxidant and cytotoxicity properties of Leonotis leonurus used in the folklore management of neurological disorders in the Eastern Cape, South Africa

Piperazine tethered bergenin heterocyclic hybrids: design, synthesis, anticancer activity, and molecular docking studies

Design, synthesis and in vitro cytotoxicity studies of novel β -carbolinium bromides

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