Synthesis and biological evaluation of 1-cyano-2-amino-benzimidazole derivatives as a novel class of antitumor agents

Zhang, Hu; Ou, Lili; Li, Sidong; Yang, Lei

doi:10.1007/s00044-013-0888-6

Cited by 25 publications

(7 citation statements)

References 22 publications

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“…azoles, azines and azoloazines (Thomae et al, 2009). It has been used effectively in the synthesis of a range of antibacterial (Paget et al, 2006), anticancer (Hu et al, 2014) and other biologically significant products (Marsault et al, 2007).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structures of (E)-2-amino-4-methylsulfanyl-6-oxo-1-(1-phenylethylideneamino)-1,6-dihydropyrimidine-5-carbonitrile and (E)-2-amino-4-methylsulfanyl-6-oxo-1-[1-(pyridin-2-yl)ethylideneamino]-1,6-dihydropyrimidine-5-carbonitrile

Mohamed-Ezzat¹,

Elgemeie

Jones

2021

Acta Crystallogr E Cryst Commun

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The title compounds 3a, C14H13N5OS, and 3b, C13H12N6OS, both show an E configuration about the N=C bond and a planar NH2 group. The molecules, which only differ in the presence of a phenyl (in 3a) or pyridyl (in 3b) substituent, are closely similar except for the different orientations of these groups. The amino hydrogen atoms form classical hydrogen bonds; in 3a the acceptors are the oxygen atom and the cyano nitrogen atom, leading to ribbons of molecules parallel to the b axis, whereas in 3b the acceptors are the oxygen atom and the pyridyl nitrogen, leading to a layer structure perpendicular to (\overline{1}01).

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structures of (E)-2-amino-4-methylsulfanyl-6-oxo-1-(1-phenylethylideneamino)-1,6-dihydropyrimidine-5-carbonitrile and (E)-2-amino-4-methylsulfanyl-6-oxo-1-[1-(pyridin-2-yl)ethylideneamino]-1,6-dihydropyrimidine-5-carbonitrile

Mohamed-Ezzat¹,

Elgemeie

Jones

2021

Acta Crystallogr E Cryst Commun

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“…Benzimidazole is yet another nitrogen heterocyclic compound with fused benzene and imidazole rings. It exhibits wide spread biological activities such as antimicrobial [20], antihistaminic [21], antiparasitic [22], antiallergic [23], anticancer [24] and antioxidant [25]. In addition, its derivatives display efficiency in material science field.…”

Section: Revised Manuscript Received On December 15 2019mentioning

confidence: 99%

Novel Benzimidazole Bejeweled Pyrazole: Synthesis, Characterization and Density Functional Theory Analysis

Sivaramakarthikeyan¹,

Padmavathy²,

Saravanan³

et al. 2019

IJEAT

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A novel benzimidazole festooned pyrazolyl acrylonitrile 6 has been synthesized with a good yield via Knoevenagel condensation method and the structure has been elucidated based on analytical and spectroscopic methods. DFT-B3LYP calculation with 6-311 G(d,p) basis set has been performed for optimization of the structure and to determine their structural - energy parameters. The HOMO –LUMO analysis and polarizability cum hyper polarizability values ensure compound 6 is likely to be NLO material that could also find use in solar cells. Besides, the electronic properties and the structural cores imply that the molecule could also serve as bioagent.

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“…Many nitrogen-heterocyclic ring systems have recently been discovered to introduce surprisingly complex biological properties, making them one of the most significant groups in medicinal chemistry. They constitute a basic scaffold in numerous drugs due to their capabilities to imitate and interact with different biological molecules, leading to remarkable pharmacological properties. − The benzimidazole scaffold participates in various compounds producing a wide range of biological activities such as antimicrobial, antiparasitic, antihistaminic, antiallergic, anticancer, and antioxidant. − The benzimidazoles could be considered as auxiliary isosters of nucleotides having a potential for chemotherapeutic applications . In addition, the orally available third-generation EGFR inhibitor nazartinib bears a benzimidazole nucleus .…”

Section: Introductionmentioning

confidence: 99%

New Benzimidazole-, 1,2,4-Triazole-, and 1,3,5-Triazine-Based Derivatives as Potential EGFR^WT and EGFR^T790M Inhibitors: Microwave-Assisted Synthesis, Anticancer Evaluation, and Molecular Docking Study

et al. 2022

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A new series of benzimidazole, 1,2,4-triazole, and 1,3,5-triazine derivatives were designed and synthesized using a microwave irradiation synthetic approach utilizing 2-phenylacetyl isothiocyanate (1) as a key starting material. All the new analogues were evaluated as anticancer agents against a panel of cancer cell lines utilizing doxorubicin as a standard drug. Most of the tested derivatives exhibited selective cytotoxic activity against MCF-7 and A-549 cancer cell lines. Furthermore, the new target compounds 5 , 6 , and 7 as the most potent antiproliferative agents have been assessed as in vitro EGFR WT and EGFR T790M inhibitors compared to the reference drugs erlotinib and AZD9291. They represented more potent suppression activity against the mutated EGFR T790M than the wild-type EGFR WT . Moreover, the compounds 5 , 6 , and 7 down-regulated the oncogenic parameter p53 ubiquitination. A docking simulation of compound 6b was carried out to correlate its molecular structure with its significant EGFR inhibition potency and its possible binding interactions within the active site of EGFR WT and the mutant EGFR T790M .

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Synthesis and biological evaluation of 1-cyano-2-amino-benzimidazole derivatives as a novel class of antitumor agents

Cited by 25 publications

References 22 publications

Crystal structures of (E)-2-amino-4-methylsulfanyl-6-oxo-1-(1-phenylethylideneamino)-1,6-dihydropyrimidine-5-carbonitrile and (E)-2-amino-4-methylsulfanyl-6-oxo-1-[1-(pyridin-2-yl)ethylideneamino]-1,6-dihydropyrimidine-5-carbonitrile

Crystal structures of (E)-2-amino-4-methylsulfanyl-6-oxo-1-(1-phenylethylideneamino)-1,6-dihydropyrimidine-5-carbonitrile and (E)-2-amino-4-methylsulfanyl-6-oxo-1-[1-(pyridin-2-yl)ethylideneamino]-1,6-dihydropyrimidine-5-carbonitrile

Novel Benzimidazole Bejeweled Pyrazole: Synthesis, Characterization and Density Functional Theory Analysis

New Benzimidazole-, 1,2,4-Triazole-, and 1,3,5-Triazine-Based Derivatives as Potential EGFR^WT and EGFR^T790M Inhibitors: Microwave-Assisted Synthesis, Anticancer Evaluation, and Molecular Docking Study

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Synthesis and biological evaluation of 1-cyano-2-amino-benzimidazole derivatives as a novel class of antitumor agents

Cited by 25 publications

References 22 publications

Crystal structures of (E)-2-amino-4-methylsulfanyl-6-oxo-1-(1-phenylethylideneamino)-1,6-dihydropyrimidine-5-carbonitrile and (E)-2-amino-4-methylsulfanyl-6-oxo-1-[1-(pyridin-2-yl)ethylideneamino]-1,6-dihydropyrimidine-5-carbonitrile

Crystal structures of (E)-2-amino-4-methylsulfanyl-6-oxo-1-(1-phenylethylideneamino)-1,6-dihydropyrimidine-5-carbonitrile and (E)-2-amino-4-methylsulfanyl-6-oxo-1-[1-(pyridin-2-yl)ethylideneamino]-1,6-dihydropyrimidine-5-carbonitrile

Novel Benzimidazole Bejeweled Pyrazole: Synthesis, Characterization and Density Functional Theory Analysis

New Benzimidazole-, 1,2,4-Triazole-, and 1,3,5-Triazine-Based Derivatives as Potential EGFRWT and EGFRT790M Inhibitors: Microwave-Assisted Synthesis, Anticancer Evaluation, and Molecular Docking Study

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New Benzimidazole-, 1,2,4-Triazole-, and 1,3,5-Triazine-Based Derivatives as Potential EGFR^WT and EGFR^T790M Inhibitors: Microwave-Assisted Synthesis, Anticancer Evaluation, and Molecular Docking Study