Coumarin – benzimidazole hybrids: A review on diverse synthetic strategies

Arya, C. G.; Chandrakanth, Munugala; Fabitha, K.; Thomas, Neethu Mariam; Pramod, Rakendu N.; Gondru, Ramesh; Banothu, Janardhan

doi:10.1016/j.rechem.2022.100631

Cited by 9 publications

(9 citation statements)

References 107 publications

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“…This might refer to altering the tertiary as well as secondary structures of proteins, which consequently leads to impairments in the biological functions of most biological proteins. Moreover, the presence of a chemical entity possessing a substituent exerts the highest activity compared with all other compounds due to it binding effectively toward the active site of the proteins [60,61]. Joy et al proposed that the anti-denaturation activity can be rationalized by the presence of electron-donating groups (-OH and -NH 2 ) and nitrogen-rich fragments, which exhibit a superior anti-inflammatory potential compared to the other pyrazole-based Schiff bases molecules [62].…”

Section: Discussionmentioning

confidence: 99%

Exploring the Potential Biological Activities of Pyrazole-Based Schiff Bases as Anti-Diabetic, Anti-Alzheimer’s, Anti-Inflammatory, and Cytotoxic Agents: In Vitro Studies with Computational Predictions

Naglah,

Almehizia,

Al-Wasidi

et al. 2024

Pharmaceuticals

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In this innovative research, we aim to reveal pyrazole-based Schiff bases as new multi-target agents. In this context, we re-synthesized three sets of pyrazole-based Schiff bases, 5a–f, 6a–f, and 7a–f, to evaluate their biological applications. The data from in vitro biological assays (including antioxidant and scavenging activities, anti-diabetes, anti-Alzheimer’s, and anti-inflammatory properties) of the pyrazole-based Schiff bases 5a–f, 6a–f, and 7a–f showed that the six pyrazole-based Schiff bases 5a, 5d, 5e, 5f, 7a, and 7f possess the highest biological properties among the compounds evaluated. The cytotoxicity against lung (A549) and colon (Caco-2) human cancer types, as well as normal lung (WI-38) cell lines, was evaluated. The data from the cytotoxicity investigation demonstrated that the three Schiff bases 5d, 5e, and 7a are active against lung (A549) cells, while the two Schiff bases 5e and 7a exhibited the highest cytotoxicity towards colon (Caco-2) cells. Additionally, the enzymatic activities against caspase-3 and Bcl-2 of the six pyrazole-based Schiff bases 5a, 5d, 5e, 5f, 7a, and 7f were evaluated. Furthermore, we assessed the in silico absorption, distribution, metabolism, and toxicity (ADMT) properties of the more potent pyrazole-based Schiff bases. After modifying the structures of the six pyrazole-based Schiff bases, we plan to further extend the studies in the future.

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Section: Discussionmentioning

confidence: 99%

Exploring the Potential Biological Activities of Pyrazole-Based Schiff Bases as Anti-Diabetic, Anti-Alzheimer’s, Anti-Inflammatory, and Cytotoxic Agents: In Vitro Studies with Computational Predictions

Naglah,

Almehizia,

Al-Wasidi

et al. 2024

Pharmaceuticals

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“…13 A list of coumarin-containing drugs currently used in the clinic is presented in Figure 1. 14 In addition to medicinal chemistry, the skeleton of coumarin can also be found in the agrochemical field as well as in the cosmetic and fragrance industries. 15 Given the importance of coumarin, the synthesis of coumarin derivatives has attracted considerable attention, in which modification of the coumarin scaffold is a practical strategy.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Coumarin derivatives are frequently found to have various biological activities, such as anti-inflammatory, , anticancer, , antimicrobial, − antioxidant, , and anti-HTV , activities, and they can also be used in photochemotherapy . A list of coumarin-containing drugs currently used in the clinic is presented in Figure . In addition to medicinal chemistry, the skeleton of coumarin can also be found in the agrochemical field as well as in the cosmetic and fragrance industries .…”

Section: Introductionmentioning

confidence: 99%

Visible Light-Induced Cross-Dehydrocoupling of 3-Cyanocoumarins with Unactivated Aliphatic Aldehydes Enables Access to 4-Acylated Coumarins

Qian

Guan

2023

J. Org. Chem.

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We report visible light-induced cross-dehydrocoupling of 3-cyanocoumarins with unactivated aliphatic aldehydes for the direct synthesis of 4-acylated coumarins. Inexpensive and readily available (n-Bu)4NBr was used as a precursor of the hydrogen atom transfer (HAT) catalyst and [Ir(ppy)2(dtbbpy)PF6] as a photocatalyst. A variety of aldehydes including linear, branched, cyclic, and α,β-unsaturated aliphatic aldehydes were suitable for this reaction yielding the desired acylated coumarin derivatives in 41–98% yields. This method provides a mild, atom-economical, and environmentally friendly synthetic route for the direct acylation of 3-cyanocoumarins. This is the first example so far of C-4 aliphatic acylation of coumarins.

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“…Coumarins, potential alternatives for chemical insecticides, are widely distributed in Compositae, Apiaceae, and Leguminosae, among others. , Even more intriguing, it displayed broad-spectrum bioactivities, including antiviral, antibacterial, anticancer, and especially potent insecticidal effects. Conversely, some coumarin analogues naturally, such as scoparone and scopoletin, displayed no toxicity toward the pollinators.…”

Section: Introductionmentioning

confidence: 99%

Development of Sustainable Insecticide Candidates for Protecting Pollinators: Insight into the Bioactivities, Selective Mechanism of Action and QSAR of Natural Coumarin Derivatives against Aphids

Zhou,

Jian,

Shao

et al. 2023

J. Agric. Food Chem.

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Plants employ abundant toxic secondary metabolites to withstand insect attack, while pollinators can tolerate some natural defensive compounds. Coumarins, as promising green alternatives to chemical insecticides, possess wide application prospects in the crop protection field. Herein, the bioactivities of 30 natural coumarin derivatives against Aphis gossypii were assessed and revealed that 6-methylcoumarin exhibited potent aphicidal activity against aphids but displayed no toxicity to honeybees. Additionally, using biochemical, bioinformatic, and molecular assays, we confirmed that the action mode of 6-methylcoumarin against aphids was by inhibiting acetylcholinesterase (AChE). Meanwhile, functional assays revealed that the difference in action site, which located in Lys585 in aphid AChE (equivalent to Val548 in honeybee AChE), was the principal reason for 6-methylcoumarin being toxic to aphids but safe to pollinators. This action site was further validated by mutagenesis data, which uncovered how 6-methylcoumarin was unique selective to the aphid over honeybee or mammalian AChE. Furthermore, a 2D-QSAR model was established, revealing that the central structural feature was H3m, which offers guidance for the future design of more potent coumarin compounds. This work provides a sustainable strategy to take advantage of coumarin analogues for pest management while protecting nontarget pollinators.

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Coumarin – benzimidazole hybrids: A review on diverse synthetic strategies

Cited by 9 publications

References 107 publications

Exploring the Potential Biological Activities of Pyrazole-Based Schiff Bases as Anti-Diabetic, Anti-Alzheimer’s, Anti-Inflammatory, and Cytotoxic Agents: In Vitro Studies with Computational Predictions

Exploring the Potential Biological Activities of Pyrazole-Based Schiff Bases as Anti-Diabetic, Anti-Alzheimer’s, Anti-Inflammatory, and Cytotoxic Agents: In Vitro Studies with Computational Predictions

Visible Light-Induced Cross-Dehydrocoupling of 3-Cyanocoumarins with Unactivated Aliphatic Aldehydes Enables Access to 4-Acylated Coumarins

Development of Sustainable Insecticide Candidates for Protecting Pollinators: Insight into the Bioactivities, Selective Mechanism of Action and QSAR of Natural Coumarin Derivatives against Aphids

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