Tetrazoles as anticancer agents: A review on synthetic strategies, mechanism of action and SAR studies

Dhiman, Neha; Kaur, Kamalpreet; Jaitak, Vikas

doi:10.1016/j.bmc.2020.115599

Cited by 91 publications

(65 citation statements)

References 127 publications

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“…Moreover, tetrazoles possess remarkable metabolic stability. According to the Drug Bank, there are more than 40 drugs that exhibit antimicrobial, anticancer [ 209 ], antiallergic, hypertensive, nootropic, and other biological activities [ 210 ]. The general approach for the synthesis of 1-unsubstituted and 1,5-disubstituted tetrazoles is the reaction of nitriles or imidoyl derivatives with inorganic or organic azides, respectively [ 210 , 211 ].…”

Section: Azoles With Four Heteroatomsmentioning

confidence: 99%

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

et al. 2021

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Diazocarbonyl compounds have found numerous applications in many areas of chemistry. Among the most developed fields of diazo chemistry is the preparation of azoles from diazo compounds. This approach represents a useful alternative to more conventional methods of the synthesis of azoles. A comprehensive review on the preparation of various azoles (oxazoles, thiazoles, imidazoles, pyrazoles, triazoles, and tetrazoles) from diazocarbonyl and related compounds is presented for the first time along with discussion of advantages and disadvantages of «diazo» approaches to azoles.

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Section: Azoles With Four Heteroatomsmentioning

confidence: 99%

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

et al. 2021

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“…Coumarins are natural and synthetic compounds reported to exhibit versatile pharmacological activities such as anticancer, anti‐inflammatory, antioxidant, antituberculosis, anti‐microbial, antidepressant, etc [69] . Coumarins can inhibit proliferation of cells, angiogenesis and induce apoptosis by acting on various biological targets such as telomerase enzyme, aromatase enzyme, protein kinase‐like VEGFR‐2, downregulation o oncogene expression, causes capspase‐9 mediated apoptosis [70–71] and also inhibit PI3 K/AKT singling pathway leading to G2 M phase arrest and apoptosis [72] . Irosustat contains coumarin scaffold and used in the treatment of various cancer.…”

Section: Imidazole Hybridizes With Other Anticancer Pharmacophoresmentioning

confidence: 99%

Hybridization of Imidazole with Various Heterocycles in Targeting Cancer: A Decade's Work

Teli¹,

Chawla²

2021

ChemistrySelect

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Cancer is the world‘s biggest global health concern. The prevalence and mortality rates of cancer remain high despite significant progress in cancer therapy. The search for more effective, as well as less toxic treatment methods for cancer, is at the focus of current studies. Approximately 24.6 million people are suffering from cancer across the world as per the world health organization (WHO). In the year 2020, approximately 10 million deaths were reported due to cancer which has emerged as the second leading cause of mortality across the globe. Anticancer medicines have played a pivotal role in the medication of different types of cancers; however, they are associated with several side effects and relevance of drug resistance which evoke an immediate need for designing of new anticancer agents with multitargeted effect. Imidazole is a heterocyclic compound privileged with considerable anticancer activities and some imidazole derivatives have already got approval to treat cancer. Many hybrid molecules are available that play an important role in the treatment of cancer like chalcone, pyrazole, purine, triazine etc., and their pharmacophore provide the anticancer drug with low drug resistance and high efficacy, with low chances of toxicity and side effects. This review provides various approaches for the drug development of new safe and efficient antitumor agents imidazole hybrids with other heterocyclic moieties. An attempt has been made to advancement of the anticancer potential of the derivatives and hybrids of imidazole having intact or condensed imidazole moiety in the last decade along with the structure‐activity relationship studies, and mechanism of action.

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“…To date, a multitude of synthetic protocols for the incorporation of a tetrazole moiety has been introduced. [2,[61][62][63][64] However, the most convenient and simple methodology for the formation of 5-substituted 1H-tetrazoles is the 1,3-dipolar cycloaddition reaction nitriles with azides. [65][66][67][68][69][70][71] Despite the utility of some of these protocols to access 2H-indazoles and 5-Substituted 1H-tetrazoles, unfortunately, some of these pathways have drawbacks, such as non-regioselectivity, tedious procedures for the preparation of starting materials, unsatisfactory yields, long reaction times, the application of expensive ligands or metals, harsh reaction conditions, and highly toxic catalysts.…”

Section: Introductionmentioning

confidence: 99%

“…To date, a multitude of synthetic protocols for the incorporation of a tetrazole moiety has been introduced [2,61–64] …”

Section: Introductionmentioning

confidence: 99%

Copper(I) Complex of Dihydro Bis(2‐Mercapto Benzimidazolyl) Borate as an Efficient Homogeneous Catalyst for the Synthesis of 2H‐Indazoles and 5‐Substituted 1H‐Tetrazoles

et al. 2021

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In this work, catalytic activity of a series of copper(I) complexes containing dihydrobis(2-mercapto-benzimidazolyl) borate (Bb), and phosphine co-ligands was investigated in the synthesis of N-heterocycle compounds including 2H-indazoles and 5-substituted 1H-tetrazoles. The copper(I) complex containing tricyclohexylphosphine co-ligand, [Cu(Bb)(PCy 3)], displayed the highest catalytic activities for the formation of 2H-indazoles and 1H-tetrazoles. Apart from the nontoxicity and strong σ-donating ability of the introduced ligands, the introduced catalyst required easy handling processes. The catalytic reactions were successfully performed at low catalyst loadings in either PEG-200 or DMF and in relatively short reaction times. The diversity of these reactions was also explored with 20 and 12 examples. Finally, the current catalytic system is amenable to large-scale production of these N-heterocycle compounds.

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Tetrazoles as anticancer agents: A review on synthetic strategies, mechanism of action and SAR studies

Cited by 91 publications

References 127 publications

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

Hybridization of Imidazole with Various Heterocycles in Targeting Cancer: A Decade's Work

Copper(I) Complex of Dihydro Bis(2‐Mercapto Benzimidazolyl) Borate as an Efficient Homogeneous Catalyst for the Synthesis of 2H‐Indazoles and 5‐Substituted 1H‐Tetrazoles

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