Synthesis and biological evaluation of triazole and isoxazole-tagged benzothiazole/benzoxazole derivatives as potent cytotoxic agents

Dadmal, Tulshiram L.; Appalanaidu, K.; Kumbhare, Ravindra M.; Mondal, Tanmoy; Ramaiah, M. Janaki; Bhadra, Manika Pal

doi:10.1039/c8nj01249k

Cited by 28 publications

(16 citation statements)

References 56 publications

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“…1,2,3-Triazole-linked isoxazole-benzothiazole-benzoxazole hybrids were prepared and their anticancer potency was evaluated on cancer A549 and HeLa cells, as well as normal HEK-293 cells. 81 The lead compound in the present study was compound 43 (Fig. 6, IC 50 = 1.768 [HeLa] and 2.594 [A549] µM).…”

Section: Diverse 123-triazole-containing Heterocyclic Hybridsmentioning

confidence: 97%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

575

289

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A B S T R A C TThe 1,2,3-triazole ring is a major pharmacophore system among nitrogen-containing heterocycles. These fivemembered heterocyclic motifs with three nitrogen heteroatoms can be prepared easily using 'click' chemistry with copper-or ruthenium-catalysed azide-alkyne cycloaddition reactions. Recently, the 'linker' property of 1,2,3-triazoles was demonstrated, and a novel class of 1,2,3-triazole-containing hybrids and conjugates was synthesised and evaluated as lead compounds for diverse biological targets. These lead compounds have been demonstrated as anticancer, antimicrobial, anti-tubercular, antiviral, antidiabetic, antimalarial, anti-leishmanial, and neuroprotective agents. The present review summarises advances in lead compounds of 1,2,3-triazolecontaining hybrids, conjugates, and their related heterocycles in medicinal chemistry published in 2018. This review will be useful to scientists in research fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology. Chemistry: synthesis and properties of the 1,2,3-triazolesThe general synthetic route of 1,2,3-triazoles using click chemistry is described in Scheme 1A. The most popular route to 1,2,3-triazoles is Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition, which is the https://doi.

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Section: Diverse 123-triazole-containing Heterocyclic Hybridsmentioning

confidence: 97%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

575

289

View full text Add to dashboard Cite

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“…2-Aminobenzothiazoles demonstrate high antiviral activity [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ], which is especially important in this period of global COVID-19 pandemic. They also possess antimicrobial [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ], antioxidant [ 20 ], anti-inflammatory [ 21 , 22 , 23 , 24 ], analgesic [ 24 ], antidepressant [ 25 , 26 ], anticonvulsant [ 27 , 28 , 29 ], anti-diabetic [ 21 , 30 ], antitumor [ 31 , 32 , 33 , 34 , 35 ], antituberculosis [ 14 , 36 ] activity. Their derivatives show also antimalarial [ 37 , 38 ], insecticide [ 39 ] and herbicide effect [ 40 ].…”

Section: Aminobenzothiazolesmentioning

confidence: 99%

“…The presence of various pharmacophores in the synthesized compounds not only enhances the antitumor effect in vivo but also promotes new mechanisms of action. Triazole and isoxazole-tagged benzothiazole/benzoxazole derivatives 35a-c and 36a-g were synthesized as potent cytotoxic agents by multistep synthesis starting from N-propargylation of the Boc-protected 2-aminobenzothiazole, as shown in Scheme 28 [33]. The key intermediate A was converted to the target products, either directly or after deprotection with trifluoroacetic acid, using Cu-catalyzed Sharpless click chemistry concept by the reaction with different amide azides.…”

Section: Scheme 27 Synthesis Of Benzothiazole-imidazolidines 34a-hmentioning

confidence: 99%

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

2021

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The review is devoted to modern trends in the chemistry of 2-amino and 2-mercapto substituted benzothiazoles covering the literature since 2015. The reviewed heterocycles belong to biologically active and industrially demanded compounds. Newly developed synthesis methods can be divided into conventional multistep processes and one-pot, atom economy procedures, realized using green chemistry principles and simple reagents. The easy functionalization of the 2-NH2 and 2-SH groups and the benzene ring of the benzothiazole moiety allows considering them as highly reactive building blocks for organic and organoelement synthesis, including the synthesis of pharmacologically active heterocycles. The review provides a summary of findings, which may be useful for developing new drugs and materials and new synthetic approaches and patterns of reactivity.

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“…Benzoxazole-isoxazole-1,2,3-triazole derivative 1,2,3-Triazole [56,57] and oxazole [57,58] are previously reported to have shown cytotoxic activity. Dadmal [59] and team have coupled this 1,2,3-triazole and oxazole moiety with benzothiazole and benzoxazole moiety (Fig. 31), and cytotoxic effect was evaluated against human cancer cell lines Hela (cervical) and A549 (lungs).…”

Section: Benzoxazole-sulphamide Derivativementioning

confidence: 99%

Anticancer activity of benzoxazole derivative (2015 onwards): a review

Ghoshal

Patel

2020

Futur J Pharm Sci

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Background According to the report published recently by the World Health Organization, the number of cancer cases in the world will increase to 22 million by 2030. So the anticancer drug research and development is taking place in the direction where the new entities are developed which are low in toxicity and are with improved activity. Benzoxazole and its derivative represent a very important class of heterocyclic compounds, which have a diverse therapeutic area. Recently, many active compounds synthesized are very effective; natural products isolated with benzoxazole moiety have also shown to be potent towards cancer. Main text In the last few years, many research groups have designed and developed many novel compounds with benzoxazole as their backbone and checked their anticancer activity. In the review article, the recent developments (mostly after 2015) made in the direction of design and synthesis of new scaffolds with very potent anticancer activity are briefly described. The effect of various heterocycles attached to the benzoxazole and their effect on the anticancer activity are thoroughly studied and recorded in the review. Conclusion These compiled data in the article will surely update the scientific community with the recent development in this area and will provide direction for further research in this area.

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Synthesis and biological evaluation of triazole and isoxazole-tagged benzothiazole/benzoxazole derivatives as potent cytotoxic agents

Abstract: Cancer is a major health problem and the most upsetting disease in humans, leading to death in both developed and developing countries.

Cited by 28 publications

References 56 publications

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

Anticancer activity of benzoxazole derivative (2015 onwards): a review

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