Synthesis and biological evaluation of benzimidazole–oxindole conjugates as microtubule-targeting agents

Kamal, Ähmed; Nagaseshadri, Bobburi; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Reddy, C. Suresh

doi:10.1016/j.bioorg.2015.09.003

Cited by 23 publications

(9 citation statements)

References 41 publications

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“…A novel series of aminobenzothiazole linked to pyrazolo[1,5-a]pyrimidine conjugates was synthesized by Kamal et al and evaluated for their antitumor activities against five human cancer cell lines. The in vitro screening results disclosed that the 4-fluoro substituted derivatives exhibit a potent and selective anticancer activity with IC 50 value of 1.94–3.46 μM [ 133 ]. It has been subjected to more detailed biological studies such as cell cycle analysis, tubulin polymerization studies, and Immunohistochemistry studies on tubulin.…”

Section: Benzazolesmentioning

confidence: 99%

“…Their finding implies that conjugate 31 with a difluoro moiety at position 3 and 5 on phenyl ring showed a significant cytotoxicity against breast cancer cell line (MCF-7) with an IC 50 value of 1.59 μM. Molecular docking studies have been performed to investigate the action mode of this compound and it indicated efficient binding with the colchicine binding site [ 133 ].…”

Section: Benzazolesmentioning

confidence: 99%

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Importance of Fluorine in Benzazole Compounds

2020

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Fluorine-containing heterocycles continue to receive considerable attention due to their unique properties. In medicinal chemistry, the incorporation of fluorine in small molecules imparts a significant enhancement their biological activities compared to non-fluorinated molecules. In this short review, we will highlight the importance of incorporating fluorine as a basic appendage in benzothiazole and benzimidazole skeletons. The chemistry and pharmacological activities of heterocycles containing fluorine during the past years are compiled and discussed.

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Section: Benzazolesmentioning

confidence: 99%

Section: Benzazolesmentioning

confidence: 99%

Importance of Fluorine in Benzazole Compounds

2020

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“…Compound 406 was found to be the most active molecule (GI 50 = 0.24 μM) in reference to colchicine and vinblastine sulphate as reference drugs. Ahmed Kamal et al worked on a series of benzimidazole‐oxindole conjugates and evaluated them for their cytotoxic potential against human breast cancer cell line (MCF‐7) (Scheme ). Compound 420c with IC 50 value 1.12 μM is found to be most potent against nocodazole as the standard drug.…”

Section: Pharmacological and Synthetic Profiles Of Benzimidazole Derimentioning

confidence: 99%

Benzimidazole Scaffold as Anticancer Agent: Synthetic Approaches and Structure–Activity Relationship

Shrivastava

Naim

Alam

et al. 2017

Archiv der Pharmazie

131

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Cancer, also known as malignant neoplasm, is a dreadful disease which involves abnormal cell growth having the potential to invade or spread to other parts of the body. Benzimidazole is an organic compound that is heterocyclic and aromatic in nature. It is a bicyclic compound formed by the fusion of the benzene and imidazole ring systems. It is an important pharmacophore and a privileged structure in medicinal chemistry. According to the World Health Organisation (2015 survey), one in six deaths is due to cancer around the globe, accounting for 8.8 million deaths of which 70% of the cases were from low- and middle-income countries. In the efforts to develop suitable anticancer drugs, medicinal chemists have focussed on benzimidazole derivatives. This review article covers the current development of benzimidazole-based anticancer agents along with the synthetic approaches and structure-activity relationships (SAR).

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“…In the same year, they designed and synthesised two benzimidazole-linked oxindoles by employing Knoevenagel condensation. [104] Different benzimidazole esters have been constructed from oxidative cyclisation of methyl ester of 3,4diamino benzoic acid with different benzaldehydes yielded one series and with thiophene-2-aldehyde resulted in another series as starting materials. Further, the respective aldehydes were condensed with diverse aldehydes, resulting in 24 derivatives.…”

Section: Oxindolementioning

confidence: 99%

Contribution of Knoevenagel Condensation Products toward the Development of Anticancer Agents: An Updated Review

2022

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Knoevenagel condensation is an entrenched, prevailing, prominent arsenal following greener principles in the generation of α, β-unsaturated ketones/carboxylic acids by involving carbonyl functionalities and active methylenes. This reaction has proved to be a major driving force in many multicomponent reactions indicating the prolific utility toward the development of biologically fascinating molecules. This eminent reaction was acclimatised on different pharmacophoric aldehydes (benzimidazole, β-carboline, phenanthrene, indole, imidazothiadiazole, pyrazole etc.) and active methylenes (oxindole, barbituric acid, Meldrum's acid, thiazolidinedione etc.) to generate the library of chemical compounds. Their potential was also explicit to understand the significance of functionalities involved, which thereby evoke further developments in drug discovery. Furthermore, most of these reaction products exhibited remarkable anticancer activity in nanomolar to micromolar ranges by targeting different cancer targets like DNA, microtubules, Topo-I/II, and kinases (PIM, PARP, NMP, p300/CBP) etc. This review underscores the efficiency of the Knoevenagel condensation explored in the past six-year to generate molecules of pharmacological interest, predominantly toward cancer. The present review also provides the aspects of structure-activity relationships, mode of action and docking study with possible interaction with the target protein.

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Synthesis and biological evaluation of benzimidazole–oxindole conjugates as microtubule-targeting agents

Cited by 23 publications

References 41 publications

Importance of Fluorine in Benzazole Compounds

Importance of Fluorine in Benzazole Compounds

Benzimidazole Scaffold as Anticancer Agent: Synthetic Approaches and Structure–Activity Relationship

Contribution of Knoevenagel Condensation Products toward the Development of Anticancer Agents: An Updated Review

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