Design, synthesis, antimicrobial evaluation, and molecular docking of novel chiral urea/thiourea derivatives bearing indole, benzimidazole, and benzothiazole scaffolds

Lafzi, Ferruh; Kılıç, Deryanur; Yildiz, Melike; Saraçoğlu, Nurullah

doi:10.1016/j.molstruc.2021.130566

Cited by 16 publications

(4 citation statements)

References 37 publications

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“…Thiourea is a bioisostere of urea and is reported to exhibit various biological activities such as anticancer, 12,13 antimicrobial, 14 antitubercular, 15 antidiabetic, 16 etc. Some of the thiourea derivatives as listed in Fig.…”

Section: Staphylococcus Aureus (Mrsa) and Vancomycin-resistantmentioning

confidence: 99%

Synthesis and biological evaluation of new naphthalimide–thiourea derivatives as potent antimicrobial agents active against multidrug-resistant Staphylococcus aureus and Mycobacterium tuberculosis

Rana,

Parupalli,

Akhir

et al. 2024

RSC Med. Chem.

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Section: Staphylococcus Aureus (Mrsa) and Vancomycin-resistantmentioning

confidence: 99%

Synthesis and biological evaluation of new naphthalimide–thiourea derivatives as potent antimicrobial agents active against multidrug-resistant Staphylococcus aureus and Mycobacterium tuberculosis

Rana,

Parupalli,

Akhir

et al. 2024

RSC Med. Chem.

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“…On the other hand, urea derivatives are widely applied in medicinal synthesis due to their various biological activities, such as anti-inflammatory ( Drexel et al, 2019 ), antitumor activities ( Kang et al, 2019 ; Kilic-Kurta et al, 2020 ), and antimicrobial ( Lafzi et al, 2021 ). Recent reports showed that urea derivatives could inhibit cell signaling transduction, such as RAS-RAFMEK-ERK signaling pathway and PI3K/Akt/mTOR pathway ( Li et al, 2019 ), and inhibit protein activity, such as mTORC1 and mTORC2 ( Gao et al, 2018 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antitumor Evaluation of Menthone-Derived Pyrimidine-Urea Compounds as Potential PI3K/Akt/mTOR Signaling Pathway Inhibitor

et al. 2022

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A series of novel menthone derivatives bearing pyrimidine and urea moieties was designed and synthesized to explore more potent natural product-derived antitumor agents. The structures of the target compounds were confirmed by FTIR, NMR, and HRMS. The in vitro antitumor activity was tested by standard methyl thiazolytetrazolium assay and showed that 4i, 4g, 4s, and 4m are the best compounds with IC50 values of 6.04 ± 0.62µM, 3.21 ± 0.67µM, 19.09 ± 0.49µM, and 18.68 ± 1.53µM, against Hela, MGC-803, MCF-7, and A549, respectively. The results of the preliminary action mechanism studies showed that compound 4i, the representative compound, could induce cell apoptosis in Hela cells in a dose-dependent manner and might arrest the cell cycle in the G2/M phase. Furthermore, the results of network pharmacology prediction and Western blot experiments indicated that compound 4i might inhibit Hela cells through inhibit PI3K/Akt/mTOR signaling pathway. The binding modes and the binding sites interactions between compound 4i and the target proteins were predicted preliminarily by the molecular docking method.

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“…Benzothiazole, a fused heterocycle, which has been widely used in pesticide due to its antibacterial, [2][3][4][5][6][7] antiviral, [8][9][10] antifungal, [11,12] antitumor [13][14][15][16] insecticidal and herbicidal properties. [17,18] Up to now, a variety of efficient pesticides based on benzothiazole skeleton had come into the market, thiabendazole, benthiavalicarb-isopropyl, clothianidin, thiamethoxam, methabenzthiazuron, mefenacet, and dufulin are widely applied to agriculture.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of novel 1,4‐pentadien‐3‐one derivatives bearing a benzothiazole moiety

Wang

Zhou

Sun

et al. 2021

Journal of Heterocyclic Chem

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In search of novel and efficient pesticides to combat increasingly resistant plant bacteria, in this work, 17 novel benzothiazole decorated penta-1,4-diene-3-one derivatives were designed and synthesized, the structures of all new compounds were systematically characterized via 1 H-NMR, 13 C-NMR, and HRMS. The results of the bioactivity study indicated that some compounds presented efficient antibacterial activity against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. Citri (Xac). Among them, compounds 3i and 3q exhibited the lowest EC 50 values of 11.9 and 28.5 μg ml À1 toward Xoo and Xac, respectively, both of them did better than those of thiodiazole copper (109.3 and 87.6 μg ml À1 , respectively) and bismerthiazol (73.5 and 55.4 μg ml À1 , respectively). Furthermore, SEM images further validated that the target compound 3i could distinctly make cell membrane destruction of Xoo.

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Design, synthesis, antimicrobial evaluation, and molecular docking of novel chiral urea/thiourea derivatives bearing indole, benzimidazole, and benzothiazole scaffolds

Cited by 16 publications

References 37 publications

Synthesis and biological evaluation of new naphthalimide–thiourea derivatives as potent antimicrobial agents active against multidrug-resistant Staphylococcus aureus and Mycobacterium tuberculosis

Synthesis and biological evaluation of new naphthalimide–thiourea derivatives as potent antimicrobial agents active against multidrug-resistant Staphylococcus aureus and Mycobacterium tuberculosis

Synthesis and Antitumor Evaluation of Menthone-Derived Pyrimidine-Urea Compounds as Potential PI3K/Akt/mTOR Signaling Pathway Inhibitor

Synthesis and antibacterial activity of novel 1,4‐pentadien‐3‐one derivatives bearing a benzothiazole moiety

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