Synthesis and antibacterial activity of 3-substituted 1-(2-methyl-5-nitrophenyl)-5-oxopyrrolidine derivatives

Balandis, Benas; Anusevičius, Kazimieras; Šiugždaitė, Jūratė; Kantminienė, Kristina; Mickevičius, Vytautas

doi:10.1007/s11164-019-03916-y

Cited by 8 publications

(1 citation statement)

References 36 publications

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“…We also tested novel compound effect on cancer cell spheroid (three-dimensional cultures) growth, as this model much better represents the real spatial connections between cells found in real tumor, compared to monolayers cell cultures [18,19]. As a continuation of our interest in further search for the nitrogen-containing heterocyclic molecules possessing biological activity [20][21][22], we report the synthesis of a series of compounds bearing benzenesulfonamide and imidazole moieties, and evaluation of their anticancer activity.…”

Section: Chemistrymentioning

confidence: 99%

Exploration of Benzenesulfonamide-Bearing Imidazole Derivatives Activity in Triple-Negative Breast Cancer and Melanoma 2D and 3D Cell Cultures

2021

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Heterocyclic compounds are one of the main groups of organic compounds possessing wide range of applications in various areas of science and their derivatives are present in many bioactive structures. They display a wide variety of biological activities. Recently, more and more attention has been focused to such heterocyclic compounds as azoles. In this work, we have synthesized a series of new imidazole derivatives incorporating a benzenesulfonamide moiety in their structure, which then were evaluated for their cytotoxicity against human triple-negative breast cancer MDA-MB-231 and human malignant melanoma IGR39 cell lines by MTT assay. Benzenesulfonamide-bearing imidazole derivatives containing 4-chloro and 3,4-dichlorosubstituents in benzene ring, and 2-ethylthio and 3-ethyl groups in imidazole ring have been determined as the most active compounds. Half-maximal effective concentration (EC50) of the most cytotoxic compound was 27.8 ± 2.8 µM against IGR39 cell line and 20.5 ± 3.6 µM against MDA-MB-231 cell line. Compounds reduced cell colony formation of both cell lines and inhibited the growth and viability of IGR39 cell spheroids more efficiently compared to triple-negative breast cancer spheroids.

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Section: Chemistrymentioning

confidence: 99%

Exploration of Benzenesulfonamide-Bearing Imidazole Derivatives Activity in Triple-Negative Breast Cancer and Melanoma 2D and 3D Cell Cultures

2021

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Novel Schiff bases–based thiophenes: Design, synthesis and biological evaluation

Puthran

Poojary

Nayak

et al. 2020

J Chinese Chemical Soc

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Abstract2‐amino‐5‐(3‐fluoro‐4‐methoxyphenyl)thiophene‐3‐carbonitrile derivatives have been synthesized from 1‐(3‐fluoro‐4‐methoxyphenyl)ethanone, malononitrile, mild base, and sulfur powder using the Gewald method through a multistep reaction sequence. The structures of newly synthesized compounds were established on the basis of their elemental analyses, IR, 1H NMR, 13C NMR, and mass spectral data, and then synthesized compounds were screened for their in vitro antimicrobial activity. Among them, derivatives 3b (thiphene), 3f (pyrazole), and 3d (halogen) showed good activity and remaining derivatives exhibited moderate activity.

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Synthesis of 2‐aminothiazoles containing 3‐hydroxypyran‐4‐one fragment based on condensation of substituted α‐arylaminoketones with thiourea

Komogortsev,

Melekhina,

Milyutin

et al. 2024

Journal of Heterocyclic Chem

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Condensation of α‐arylaminoketones bearing 3‐hydroxypyran‐4‐one fragment with thiourea was studied. Based on considered investigation, the method for the synthesis of terarylenes with 2‐aminothiazole bridge was elaborated. The presented process is the first example of construction of thiazole core starting from α‐aminoketone precursor. The advantages of developed approach are easily available starting materials and convenient isolation of target products avoiding chromatographic purification. The structure of one of prepared products was confirmed by x‐ray analysis. The synthetic utility of obtained 2‐aminothiazoles with allomaltol substituent was demonstrated by reaction at amino and hydroxyl groups.

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Synthesis and antibacterial activity of 3-substituted 1-(2-methyl-5-nitrophenyl)-5-oxopyrrolidine derivatives

Cited by 8 publications

References 36 publications

Exploration of Benzenesulfonamide-Bearing Imidazole Derivatives Activity in Triple-Negative Breast Cancer and Melanoma 2D and 3D Cell Cultures

Exploration of Benzenesulfonamide-Bearing Imidazole Derivatives Activity in Triple-Negative Breast Cancer and Melanoma 2D and 3D Cell Cultures

Novel Schiff bases–based thiophenes: Design, synthesis and biological evaluation

Synthesis of 2‐aminothiazoles containing 3‐hydroxypyran‐4‐one fragment based on condensation of substituted α‐arylaminoketones with thiourea

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