Green Solvent-Free Synthesis of New
            <i>N</i>
            -Heterocycle-L-Ascorbic Acid Hybrids and Their Antiproliferative Evaluation

Bistrović, Andrea; Macan, Andrijana Meščić; Jakopec, Silvio; Prpić, Helena; Hrkać, Anja Harej; Pavelić, Sandra Kraljević; Raić‐Malić, Silvana

doi:10.4155/fmc-2022-0047

Cited by 3 publications

(1 citation statement)

References 58 publications

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“…The promising antiproliferative activity of ferrocenes conjugated with N ‐heterocycle in I − III via 1,2,3‐triazole 12,14,39 prompted us to further study the anticancer potential of a series of 1,1′‐disubstituted ferrocene derivatives bearing quinoline ( 5a – 5d and 6a – 6d ) or quinolone ( 7a , 7b , 8a , and 8b ) moiety (Figure 1). In contrast to the well‐developed milling procedures of click reactions, 38,40–42 this is the first attempt of LAG mechanochemical synthesis of ferrocenes containing 1,2,3‐triazole moiety, which may guide further research on LAG mechanosynthesis in medicinal organometallic chemistry. The antiproliferative activity of novel compounds on malignant tumor and non‐tumor cells was evaluated, and bis‐6‐methylquinolone ferrocene derivative 8b with best inhibitory effect on T‐cell lymphoma (HuT78) cells was further evaluated by cell cycle analysis and measurement of mitochondrial membrane potential.…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical synthesis and antiproliferative activity of novel ferrocene quinoline/quinolone hybrids

Maračić

Jakopec

Piškor

et al. 2023

Applied Organom Chemis

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The synthesis of novel 1,1′‐disubstituted ferrocene conjugates appended with N‐1 and O‐4 alkylated quinolone and quinoline was reported. The target compounds were synthesized employing a liquid‐assisted grinding (LAG) mechanochemical method in copper‐catalyzed azide‐alkyne cycloaddition (CuAAC) to obtain ferrocene−quinoline/quinolone hybrids (5a–5d, 6a–6d, 7a, 7b, 8a, and 8b) in higher yields and shorter reaction time compared to a conventional method, thus proving superiority of mechanochemistry versus conventional synthesis. Bis‐quinoline and bis‐quinolone ferrocene derivatives were evaluated for their antiproliferative effects on five selected tumor and two non‐tumor cell lines. Bis‐6‐methylquinolone–ferrocene conjugate 8b showed the best antiproliferative effect on T‐cell lymphoma (HuT78) cells (IC50 = 14.8 μM) and no cytotoxicity on both non‐tumor MDCK1 and BJ cells. Results obtained after mitochondrial membrane potential (∆Ψm) measurement using flow cytometry showed that compound 8b caused accumulation of HuT78 cells in subG0/G1 phase, disturbance of mitochondrial membrane potential, and apoptosis. The structure of the quinolone and ferrocene hybrid 8b can be further optimized to obtain candidates with better inhibitory effects on HuT78 cells.

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Section: Introductionmentioning

confidence: 99%

Mechanochemical synthesis and antiproliferative activity of novel ferrocene quinoline/quinolone hybrids

Maračić

Jakopec

Piškor

et al. 2023

Applied Organom Chemis

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Solvent-Free Synthesis of Bioactive Heterocycles

Bajpai,

Kamboj,

Singh

et al. 2024

COCAT

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The main emphasis of green chemistry is to reduce environmental pollution. Its main goal is to adopt a cost-effective and harmless strategy for human health and the environment. The green synthetic routes have succeeded in adopting solvent-free conditions as an effective tool for sustainability. Heterocycles are organic compounds that are widely distributed by nature. Many of them possess medicinal and pharmacological properties, as this heterocyclic moiety is found in many drugs. The solvent-free strategies for the Synthesis of bioactive heterocycles are, now-adays, regarded as an important objective. Solvent-free reactions are eco-friendly, cost-effective, and an environmentally benign route in organic transformation methods because of their effi-ciency, reduced reaction time, and high yields, thereby saving energy. This mini-review focuses on the environmentally benign solvent-free Synthesis of heterocycles and their potential pharma-cological applications.

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Keto-Bridged Dual Triazole-Linked Benzenesulfonamides As Potent Carbonic Anhydrase and Cathepsin B Inhibitors

Vats,

Arya,

Kumar

et al. 2023

Future Med. Chem.

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Background: Inhibition of human carbonic anhydrase (hCA) isoforms IX and XII with concurrent inhibition of cathepsin B is a promising approach for targeting cancers. Methods/results: 28 keto-bridged dual triazole-containing benzenesulfonamides were synthesized and tested, following the multitarget approach, for their efficacy as inhibitors of cathepsin B and hCA isoforms (I, II, IX, XII). The synthesized compounds showed excellent inhibition of CA isoforms (IX and XII) and cathepsin B. Compound 8i exhibited better and more selective inhibition of the cancer-associated isoform hCA IX as compared with acetazolamide (reference drug) and SLC-0111 (potent lead as carbonic anhydrase inhibitor). Molecular docking studies were also carried out. Conclusion: The present work gives important generalizations for the development of isoform-selective hCA inhibitors endowed with anti-cathepsin properties.

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Green Solvent-Free Synthesis of New N -Heterocycle-L-Ascorbic Acid Hybrids and Their Antiproliferative Evaluation

Cited by 3 publications

References 58 publications

Mechanochemical synthesis and antiproliferative activity of novel ferrocene quinoline/quinolone hybrids

Mechanochemical synthesis and antiproliferative activity of novel ferrocene quinoline/quinolone hybrids

Solvent-Free Synthesis of Bioactive Heterocycles

Keto-Bridged Dual Triazole-Linked Benzenesulfonamides As Potent Carbonic Anhydrase and Cathepsin B Inhibitors

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