Benzimidazole-Quinoline Hybrid Scaffold as Promising Pharmacological Agents: A Review

Devleena, Tiglani; Salahuddin,; Mazumder, Avijit; Yar, Mohammad Shahar; Kumar, Rajnish; Ahsan, Mohamed Jawed

doi:10.1080/10406638.2021.1942933

Cited by 17 publications

(7 citation statements)

References 59 publications

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“…Heterocycles, especially heterocycles containing nitrogen, are considered the most fundamental structural units in medicinal chemistry research and development [ 1 , 2 ]. Among several heterocyclic structures, syntheses and biological applications of benzimidazole have been subjected to various studies from many research groups [ 3 , 4 , 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Docking Study, and Antiproliferative Evaluation of Novel Schiff Base–Benzimidazole Hybrids with VEGFR-2 Inhibitory Activity

et al. 2023

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A new series of Schiff–benzimidazole hybrids 3a–o has been designed and synthesized. The structure of the target compounds was proved by different spectroscopic and elemental analysis tools. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI single- and five-dose protocols. Consequently, four compounds were further examined against the most sensitive lung cancer A549 and NCI-H460 cell lines. Compounds 3e and 3g were the most active, achieving 3.58 ± 0.53, 1.71 ± 0.17 and 1.88 ± 0.35, 0.85 ± 0.24 against A549 and NCI-H460 cell lines, respectively. Moreover, they showed remarkable inhibitory activity on the VEGFR-2 TK with 86.23 and 89.89%, respectively, as compared with Sorafenib (88.17%). Moreover, cell cycle analysis of NCI-H460 cells treated with 3e and 3g showed cellular cycle arrest at both G1 and S phases (supported by caspases-9 study) with significant pro-apoptotic activity, as indicated by annexin V-FITC staining. The binding interactions of these compounds were confirmed through molecular docking studies; the most active compounds displayed complete overlay with, and a similar binding mode and pose to, Sorafenib, a reference VEGFR-2 inhibitor.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Docking Study, and Antiproliferative Evaluation of Novel Schiff Base–Benzimidazole Hybrids with VEGFR-2 Inhibitory Activity

et al. 2023

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“…It was seen that the pharmacological activity of the quinoline ring changes when it associates with another N‐containing heterocycle moiety, i. e., benzimidazole. Also, we recently reported the biological activity of tetracyclic benzimidazoles, specifically benzimidazole[1,2‐a] quinolines bearing amino substituents with the ability to inhibit cell proliferation at sub micromolar concentrations [23] . These benzimidazole‐quinoline hybrid compounds are useful as they employ methods like molecular docking, NMR skeletons of biomolecules, and computer‐aided drug design to shorten research time as well as expenses [24] .…”

Section: Introductionmentioning

confidence: 99%

“…Also, we recently reported the biological activity of tetracyclic benzimidazoles, specifically benzimidazole [1,2-a] quinolines bearing amino substituents with the ability to inhibit cell proliferation at sub micromolar concentrations. [23] These benzimidazole-quinoline hybrid compounds are useful as they employ methods like molecular docking, NMR skeletons of biomolecules, and computer-aided drug design to shorten research time as well as expenses. [24] Some benzimidazole [1,2-a] quinoline have recently been discovered to have biologically intriguing properties [25] such as antimicrobial, antifungal, and antitumor.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, In Silico and In Vivo Evaluation of Benzimidazole‐Bearing Quinoline Schiff Bases as New Anticonvulsant Agents

et al. 2023

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Nitrogen‐containing hybrid heterocyclic compounds have been gaining attention in the field of drug discovery and development due to their diverse pharmacological activities and relatively low toxicity. This study aimed to synthesize a series of new quinoline‐bearing amino acid‐derived benzimidazole derivatives i. e. 3‐{[1‐(1H‐Benzoimidazol‐2‐yl)‐subsituted‐methyl}‐4a,8a‐ dihydro‐1H‐quinoline‐2‐one, and 3‐{[1‐(1H‐Benzoimidazol‐2‐yl)‐substituted‐methyl}‐3H‐ quinoline‐2‐thione. These compounds were synthesized by the condensation of 2‐oxo‐1,2‐dihydro‐quinoline‐3‐ carbaldehyde and 2‐the oxo‐1,2‐dihydro‐quinoline‐3‐carbaldehyde with various substituted 1‐(1H‐benzimidazole‐2‐yl)‐methylamine. After synthesizing the compound, it was subjected to various characterization techniques such as IR, 1HNMR, 13CNMR, and Mass spectroscopy. The synthesized compounds were evaluated for their potential as an anticonvulsant using the subcutaneous Pentylenetetrazol (scPTZ) method, and the results were compared with those obtained for phenytoin and carbamazepine, which were used as standard drugs. Among all the screened derivatives 4 d, 4 e, 5 a, and 5 b were found to be the most potent as compared to conventional drugs (phenytoin and carbamazepine). Also, the molecular docking analysis of the synthesized compounds showed that they share the same mechanism of action as phenytoin and carbamazepine, which involves the inhibition of voltage‐gated sodium channels. Additionally, the analysis revealed that these compounds also inhibit the NMDA receptor. Overall, the development of nitrogen‐containing hybrid heterocyclic compounds has the potential to significantly contribute to the discovery and development of new drugs with improved efficacy, selectivity, and safety profiles.

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“…20,21 Quinoxaline is a type of heterocyclic scaffold found in a wide range of compounds with biological and pharmaceutical applications. [22][23][24][25] For instance, quinoxaline derivatives show various pharmacological abilities as analgesics and anti-inflammatory, 26 antidiabetic, 27 antidepressant, 28 smooth muscle relaxant, 29 CNS therapeutic, 30,31 anticonvulsant, [32][33][34][35][36] antimicrobial, [37][38][39][40] antimycobacterial, [41][42][43][44][45] antiplasmodial and leishmanicidal, [46][47][48] anticancer, [49][50][51][52][53] and heart and renal therapeutic agents. 54 So, the quinoxaline nucleus is preferred as a model among nitrogenbased heterocycles.…”

Section: Introductionmentioning

confidence: 99%

“…For instance, quinoxaline derivatives show various pharmacological abilities as analgesics and anti-inflammatory, 26 anti-diabetic, 27 antidepressant, 28 smooth muscle relaxant, 29 CNS therapeutic, 30,31 anticonvulsant, 32–36 antimicrobial, 37–40 anti-mycobacterial, 41–45 antiplasmodial and leishmanicidal, 46–48 anticancer, 49–53 and heart and renal therapeutic agents. 54 So, the quinoxaline nucleus is preferred as a model among nitrogen-based heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Quinoxaline derivatives as a promising scaffold for breast cancer treatment

et al. 2022

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Benzimidazole-Quinoline Hybrid Scaffold as Promising Pharmacological Agents: A Review

Cited by 17 publications

References 59 publications

Design, Synthesis, Docking Study, and Antiproliferative Evaluation of Novel Schiff Base–Benzimidazole Hybrids with VEGFR-2 Inhibitory Activity

Design, Synthesis, Docking Study, and Antiproliferative Evaluation of Novel Schiff Base–Benzimidazole Hybrids with VEGFR-2 Inhibitory Activity

Synthesis, Characterization, In Silico and In Vivo Evaluation of Benzimidazole‐Bearing Quinoline Schiff Bases as New Anticonvulsant Agents

Quinoxaline derivatives as a promising scaffold for breast cancer treatment

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