Ultrasound assisted synthesis of hybrid quinoline-imidazole derivatives: a green synthetic approach

Diaconu, Dumitrela; Mantu, Dorina; Mangalagiu, Violeta; Antoci, Vasilichia; Zbancioc, Gheorghiță; Mangalagiu, Ionel I.

doi:10.1039/d1ra07484a

Cited by 7 publications

(4 citation statements)

References 43 publications

(64 reference statements)

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“…In order to obtain our QIBS and QIBC derivatives we used a similar procedure reported previously by our group 21 . The reaction pathway is straight and efficient, involving four steps indicated in Fig.…”

Section: Resultsmentioning

confidence: 99%

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Quinoline–imidazole/benzimidazole derivatives as dual-/multi-targeting hybrids inhibitors with anticancer and antimicrobial activity

Diaconu

Antoci

Mangalagiu

et al. 2022

Sci Rep

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Two new classes of hybrid quinoline–imidazole/benzimidazole derivatives (the hybrid QIBS salts and QIBC cycloadducts) were designed and synthesized to evaluate their anticancer and antimicrobial activity. The strategy adopted for synthesis is straight and efficient, in four steps: N-acylation, N-alkylation, quaternization and a Huisgen 3 + 2 cycloaddition. The in vitro single-dose anticancer assay of forty six hybrid quinoline-benzimidazole compounds reveal that one QIBS salt (11h), has an excellent quasi nonselective activity against all type of cancer cell with an excellent PGI in the area of 90–100% and very good lethality. Three others quinoline–imidazole/benzimidazole hybrids (8h, 12h, 12f) has an excellent selective activity against some cancer cell lines: breast cancer MDA-MB-468 and Leukemia HL-60 TB). The five-dose assay screening confirms that compound 11h possesses excellent anti-proliferative activity, with GI50 in the range of nano-molar, against some cancer cell lines: Leukemia HL-60 TB, Leukemia K-526, Leukemia RPMI-8226, Breast cancer MDA-MB-468, Lung cancer HOP-92 and Ovarian cancer IGROV1. The antibacterial assay indicates that three hybrid QIBS salts (12f, 12c, 12d) have an excellent activity against Gram-negative bacteria E. coli (superior to control Gentamicin) while against Gram-positive bacteria S. aureus only one compound 8i (R2 = -CF3) exhibits a significant activity (superior to control Gentamicin). The MIC assay indicates that two other compounds (11h, 12h) are biologically active to a very low concentration, in the range of nano-molar. We believe that all these excellent assets related to anticancer and antibacterial activities, make from our hybrid quinoline–imidazole/benzimidazole compounds bearing a phenyl group (R2 = –C6H5) in the para (4)-position of the benzoyl moiety a good candidate for future drug developing.

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Section: Resultsmentioning

confidence: 99%

“…In continuation of our seeking for new entities with anticancer and antimicrobial activity with quinoline and imidazole/benzimidazole skeleton 21 – 26 , we report herein the design, synthesis and biological activity of two new class of hybrid molecules with quinoline–imidazole/benzimidazole skeleton.…”

Section: Introductionmentioning

confidence: 99%

Quinoline–imidazole/benzimidazole derivatives as dual-/multi-targeting hybrids inhibitors with anticancer and antimicrobial activity

Diaconu

Antoci

Mangalagiu

et al. 2022

Sci Rep

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“…Diaconu et al used ultrasound irradiation to produce the quinoline-imidazolium hybrids by N-alkylation of the acidic nitrogen in benzimidazole with substituted ω-halogen acetophenones (Scheme 7). All derivatives including compounds 22 and 23 were reported to have improved yield when compared with conventional heating methods (Diaconu et al, 2021).…”

Section: Ultrasound-assisted Synthesismentioning

confidence: 99%

Recent advances in functionalized quinoline scaffolds and hybrids—Exceptional pharmacophore in therapeutic medicine

Elebiju

Ajani²,

Oduselu³

et al. 2023

Front. Chem.

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Quinoline is one of the most common nitrogen-containing heterocycles owing to its fascinating pharmacological properties and synthetic value in organic and pharmaceutical chemistry. Functionalization of this moiety at different positions has allowed for varying pharmacological activities of its derivative. Several publications over the last few decades have specified various methods of synthesis. This includes classical methods of synthesizing the primary quinoline derivatives and efficient methods that reduce reaction time with increased yield employing procedures that fulfill one of the twelve green chemistry principles, “safer solvent”. The metal nanoparticle-catalyzed reaction also serves as a potent and effective technique for the synthesis of quinoline with excellent atom efficiency. The primary focus of this review is to highlight the routes to synthesizing functionalized quinoline derivatives, including hybrids that have moieties with predetermined activities bound to the quinoline moiety which are of interest in synthesizing drug candidates with dual modes of action, overcoming toxicity, and resistance amongst others. This was achieved using updated literature, stating the biological activities and mechanisms through which these compounds administer relief. The ADMET studies and Structure-Activity Relationship (SAR) of novel derivatives were also highlighted to explore the drug-likeness of the quinoline-hybrids and the influence of substituent characteristics and position on the biological activity of the compounds.

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“…This transformation is particularly notable as it stands in stark contrast to the typical ring expansion reactions of benzimidazoliums, where the introduced atom originates from the parent molecule and not from an external molecule. 7…”

Section: Introductionmentioning

confidence: 99%

Carbon atom insertion into N-heterocyclic carbenes to yield 3,4-dihydroquinoxalin-2(1H)-ones

Lamb,

Koyama,

Suzuki

et al. 2024

Org. Chem. Front.

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Ultrasound assisted synthesis of hybrid quinoline-imidazole derivatives: a green synthetic approach

Abstract: A green, straightforward and efficient study for obtaining hybrid quinoline-imidazole derivatives under ultrasound (US) irradiation as well as under conventional thermal heating (TH) has been presented.

Cited by 7 publications

References 43 publications

Quinoline–imidazole/benzimidazole derivatives as dual-/multi-targeting hybrids inhibitors with anticancer and antimicrobial activity

Quinoline–imidazole/benzimidazole derivatives as dual-/multi-targeting hybrids inhibitors with anticancer and antimicrobial activity

Recent advances in functionalized quinoline scaffolds and hybrids—Exceptional pharmacophore in therapeutic medicine

Carbon atom insertion into N-heterocyclic carbenes to yield 3,4-dihydroquinoxalin-2(1H)-ones

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