Imine/amide–imidazole conjugates derived from 5-amino-4-cyano- N 1-substituted benzyl imidazole: Microwave-assisted synthesis and anticancer activity via selective topoisomerase-II-α inhibition

Negi, Arvind S.; Alex, Jimi Marin; Amrutkar, Suyog M.; Baviskar, Ashish T.; Joshi, Gaurav; Singh, Sandeep; Banerjee, Uttam Chand; Kumar, Raj

doi:10.1016/j.bmc.2015.07.020

Cited by 40 publications

(14 citation statements)

References 30 publications

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“…Recently, Negi et al reported the microwave synthesis of ten imidazoles conjugated with imine/amides and screened them for anticancer activities with seven cancer cell lines (A-459, Hep-G2, H-460, HeLa, MCF7, PC3 and IGROV-1). 123 Only three imidazoles 18a-18c ( Fig. 10) showed promising in vitro anticancer activities with low micromolar IC 50 values against A-459, Hep-G2 and H-460 cancer cell lines.…”

Section: Imidazoles As Topoisomerase Inhibitorsmentioning

confidence: 99%

Imidazoles as potential anticancer agents

2017

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Cancer is a black spot on the face of humanity in this era of science and technology. Presently, several classes of anticancer drugs are available in the market, but issues such as toxicity, low efficacy and solubility have decreased the overall therapeutic indices. Thus, the search for new promising anticancer agents continues, and the battle against cancer is far from over. Imidazole is an aromatic diazole and alkaloid with anticancer properties. There is considerable interest among scientists in developing imidazoles as safe alternatives to anticancer chemotherapy. The present article describes the structural, chemical, and biological features of imidazoles. Several classes of imidazoles as anticancer agents based on their mode of action have been critically discussed. A careful observation has been made into pharmacologically active imidazoles with better or equal therapeutic effects compared to well-known imidazole-based anticancer drugs, which are available on the market. A brief discussion of the toxicities of imidazoles has been made. Finally, the current challenges and future perspectives of imidazole based anticancer drug development are conferred.

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Section: Imidazoles As Topoisomerase Inhibitorsmentioning

confidence: 99%

Imidazoles as potential anticancer agents

2017

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“…The microwave-assisted synthesis was conducted according to Negi et al [12] with some modifications. In a 10-mL volume microwave vial, octanaldehyde (1.2 mmol, 186 µL) was dissolved in methanol (1 mL) and added dropwise to 2-(2-aminophenyl)-1 H -benzimidazole (1 mmol, 0.21 g) which was dissolved in 5 mL methanol, followed by addition of two drops of glacial acetic acid.…”

Section: Synthesis and Characterisationmentioning

confidence: 99%

Microwave synthesis, crystal structure, antioxidant, and antimicrobial study of new 6-heptyl-5,6-dihydrobenzo[4,5]imidazo[1,2-c]quinazoline compound

Hasan

Abdulmalek

Rahman

et al. 2018

Chemistry Central Journal

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BackgroundAlthough the development of antibiotic and antioxidant manufacturing, the problem of bacterial resistance and food and/or cosmetics oxidation still needs more efforts to design new derivatives which can help to minimize these troubles. Benzimidazo[1,2-c]quinazolines are nitrogen-rich heterocyclic compounds that possess many pharmaceutical properties such as antimicrobial, anticonvulsant, immunoenhancer, and anticancer.ResultsA comparative study between two methods, (microwave-assisted and conventional heating approaches), was performed to synthesise a new quinazoline derivative from 2-(2-aminophenyl)-1H-benzimidazole and octanal to produce 6-heptyl-5,6-dihydrobenzo[4,5]imidazo[1,2-c]quinazoline (OCT). The compound was characterised using FTIR, 1H and 13C NMR, DIMS, as well as X-ray crystallography. The most significant peak in the 13C NMR spectrum is C-7 at 65.5 ppm which confirms the cyclisation process. Crystal structure analysis revealed that the molecule grows in the monoclinic crystal system P21/n space group and stabilised by an intermolecular hydrogen bond between the N1–H1A…N3 atoms. The crystal packing analysis showed that the molecule adopts zig-zag one dimensional chains. Fluorescence study of OCT revealed that it produces blue light when expose to UV-light and its’ quantum yield equal to 26%. Antioxidant activity, which included DPPH· and ABTS·+ assays was also performed and statistical analysis was achieved via a paired T-test using Minitab 16 software with P < 0.05. Also, the antimicrobial assay against two Gram-positive, two Gram-negative, and one fungus was screened for these derivatives.ConclusionsUsing microwave to synthesise OCT have drastically reduced reaction time, and increased yield. OCT show good antioxidant activity in one of the tests and moderate antimicrobial activity.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0509-z) contains supplementary material, which is available to authorized users.

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“…Overall, binding pattern and docking score of the designed compound was better than I and II (See Supplementary Materials, Figure S1, Table S1). Furthermore, imidazole-fused [11,18] quinoxaline [19], in particular, imidazo[1,2-a]quinoxalines have gained significant interest due to their broad-spectrum activities [20,21], including IκB kinase (IKK) [22] and lymphocyte-specific protein tyrosine kinase (LCK) [23] inhibitory activities. In the recent past, we were interested in developing the synthetic approaches and assessing the biological activities of pyrazolo[1,5-c]quinazolines [12][13][14][15], which eventually emerged as active EGFR inhibitors [16,17].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Non-Covalent Imidazo[1,2-a]quinoxaline-Based Inhibitors of EGFR and Their Anti-Cancer Assessment

et al. 2021

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A series of 30 non-covalent imidazo[1,2-a]quinoxaline-based inhibitors of epidermal growth factor receptor (EGFR) were designed and synthesized. EGFR inhibitory assessment (against wild type) data of compounds revealed 6b, 7h, 7j, 9a and 9c as potent EGFRWT inhibitors with IC50 values of 211.22, 222.21, 193.18, 223.32 and 221.53 nM, respectively, which were comparable to erlotinib (221.03 nM), a positive control. Furthermore, compounds exhibited excellent antiproliferative activity when tested against cancer cell lines harboring EGFRWT; A549, a non-small cell lung cancer (NSCLC), HCT-116 (colon), MDA-MB-231 (breast) and gefitinib-resistant NSCLC cell line H1975 harboring EGFRL858R/T790M. In particular, compound 6b demonstrated significant inhibitory potential against gefitinib-resistant H1975 cells (IC50 = 3.65 μM) as compared to gefitinib (IC50 > 20 μM). Moreover, molecular docking disclosed the binding mode of the 6b to the domain of EGFR (wild type and mutant type), indicating the basis of inhibition. Furthermore, its effects on redox modulation, mitochondrial membrane potential, cell cycle analysis and cell death mode in A549 lung cancer cells were also reported.

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Imine/amide–imidazole conjugates derived from 5-amino-4-cyano- N 1-substituted benzyl imidazole: Microwave-assisted synthesis and anticancer activity via selective topoisomerase-II-α inhibition

Cited by 40 publications

References 30 publications

Imidazoles as potential anticancer agents

Imidazoles as potential anticancer agents

Microwave synthesis, crystal structure, antioxidant, and antimicrobial study of new 6-heptyl-5,6-dihydrobenzo[4,5]imidazo[1,2-c]quinazoline compound

Design and Synthesis of Non-Covalent Imidazo[1,2-a]quinoxaline-Based Inhibitors of EGFR and Their Anti-Cancer Assessment

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