Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole

Salahuddin,; Shaharyar, Mohammad; Mazumder, Avijit; Ahsan, Mohamed Jawed

doi:10.1016/j.arabjc.2013.02.001

Cited by 56 publications

(29 citation statements)

References 16 publications

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“…One frequently used protocol for the synthesis of benzimidazole derivatives is the coupling of o -phenylenediamines with carboxylic acids [13–14]. Another widely used procedure for the same synthesis represents the condensation of o -phenylenediamine with aldehydes.…”

Section: Introductionmentioning

confidence: 99%

Selective and eco-friendly procedures for the synthesis of benzimidazole derivatives. The role of the Er(OTf)₃ catalyst in the reaction selectivity

Cano¹,

Uranga²,

Nardi³

et al. 2016

Beilstein J. Org. Chem.

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An improved and greener protocol for the synthesis of benzimidazole derivatives, starting from o-phenylenediamine, with different aldehydes is reported. Double-condensation products were selectively obtained when Er(OTf)3 was used as the catalyst in the presence of electron-rich aldehydes. Conversely, the formation of mono-condensation products was the preferred path in absence of this catalyst. One of the major advantages of these reactions was the formation of a single product, avoiding extensive isolation and purification of products, which is frequently associated with these reactions.Theoretical calculations helped to understand the different reactivity established for these reactions. Thus, we found that the charge density on the oxygen of the carbonyl group has a significant impact on the reaction pathway. For instance, electron-rich aldehydes better coordinate to the catalyst, which favours the addition of the amine group to the carbonyl group, therefore facilitating the formation of double-condensation products.Reactions with aliphatic or aromatic aldehydes were possible, without using organic solvents and in a one-pot procedure with short reaction time (2–5 min), affording single products in excellent yields (75–99%). This convenient and eco-friendly methodology offers numerous benefits with respect to other protocols reported for similar compounds.

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Section: Introductionmentioning

confidence: 99%

Selective and eco-friendly procedures for the synthesis of benzimidazole derivatives. The role of the Er(OTf)₃ catalyst in the reaction selectivity

Cano¹,

Uranga²,

Nardi³

et al. 2016

Beilstein J. Org. Chem.

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“…Considering these recent discoveries, curcumin can be considered as an ideal lead compound for anticancer drug development. Earlier we have reported the anticancer activity of pyrazoline and oxadiazole analogues [25, 26]. Receptor tyrosine kinases (RTKs) have been shown to be key regulators of normal cellular processes and to additionally play a critical role in the development and progression of many types of cancer by binding either with polypeptide growth factors or cytokines or hormones [27].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterisation, andIn VitroAnticancer Activity of Curcumin Analogues Bearing Pyrazole/Pyrimidine Ring Targeting EGFR Tyrosine Kinase

Ahsan¹,

Khalilullah

Yasmin

et al. 2013

BioMed Research International

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In search of potential therapeutics for cancer, we described herein the synthesis, characterization, and in vitro anticancer activity of a novel series of curcumin analogues. The anticancer effects were evaluated on a panel of 60 cell lines, according to the National Cancer Institute (NCI) screening protocol. There were 10 tested compounds among 14 synthesized compounds, which showed potent anticancer activity in both one-dose and 5-dose assays. The most active compound of the series was 3,5-bis(4-hydroxy-3-methylstyryl)-1H-pyrazole-1-yl(phenyl)methanone (10) which showed mean growth percent of −28.71 in one-dose assay and GI50 values between 0.0079 and 1.86 µM in 5-dose assay.

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“…Screening test of caspase‐dependent apoptosis showed 68 and 69 to be more potent than tirapazamine upon exposure to A549 cell. Other recently established anticancer benzimidazoles are 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , and 78 (Fig. ).…”

Section: Pharmacological Activitiesmentioning

confidence: 99%

“…The most prominent benzimidazole compound in nature is N ‐ribosyldimethyl benzimidazole 10 which serves in vitamin B 12 as an axial ligand for the cobalt metal .…”

Section: Chemistrymentioning

confidence: 99%

Functionalized Benzimidazole Scaffolds: Privileged Heterocycle for Drug Design in Therapeutic Medicine

Ajani

Aderohunmu

Ikpo

et al. 2016

Archiv der Pharmazie

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Benzimidazole derivatives are crucial structural scaffolds found in diverse libraries of biologically active compounds which are therapeutically useful agents in drug discovery and medicinal research. They are structural isosteres of naturally occurring nucleotides, which allows them to interact with the biopolymers of living systems. Hence, there is a need to couple the latest information with the earlier documentations to understand the current status of the benzimidazole nucleus in medicinal chemistry research. This present work unveils the benzimidazole core as a multifunctional nucleus that serves as a resourceful tool of information for synthetic modifications of old existing candidates in order to tackle drug resistance bottlenecks in therapeutic medicine. This manuscript deals with the recent advances in the synthesis of benzimidazole derivatives, the widespread biological activities as well as pharmacokinetic reports. These present them as a toolbox for fighting infectious diseases and also make them excellent candidates for future drug design.

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Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole

Cited by 56 publications

References 16 publications

Selective and eco-friendly procedures for the synthesis of benzimidazole derivatives. The role of the Er(OTf)₃ catalyst in the reaction selectivity

Selective and eco-friendly procedures for the synthesis of benzimidazole derivatives. The role of the Er(OTf)₃ catalyst in the reaction selectivity

Synthesis, Characterisation, andIn VitroAnticancer Activity of Curcumin Analogues Bearing Pyrazole/Pyrimidine Ring Targeting EGFR Tyrosine Kinase

Functionalized Benzimidazole Scaffolds: Privileged Heterocycle for Drug Design in Therapeutic Medicine

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Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole

Cited by 56 publications

References 16 publications

Selective and eco-friendly procedures for the synthesis of benzimidazole derivatives. The role of the Er(OTf)3 catalyst in the reaction selectivity

Selective and eco-friendly procedures for the synthesis of benzimidazole derivatives. The role of the Er(OTf)3 catalyst in the reaction selectivity

Synthesis, Characterisation, andIn VitroAnticancer Activity of Curcumin Analogues Bearing Pyrazole/Pyrimidine Ring Targeting EGFR Tyrosine Kinase

Functionalized Benzimidazole Scaffolds: Privileged Heterocycle for Drug Design in Therapeutic Medicine

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Selective and eco-friendly procedures for the synthesis of benzimidazole derivatives. The role of the Er(OTf)₃ catalyst in the reaction selectivity

Selective and eco-friendly procedures for the synthesis of benzimidazole derivatives. The role of the Er(OTf)₃ catalyst in the reaction selectivity