Synthesis of New C2-Symmetric Chiral Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons

Çapan, İrfan; Servi, Süleyman

doi:10.2174/1570178616666190731105327

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2020

DOI: 10.2174/1570178616666190731105327

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Synthesis of New C2-Symmetric Chiral Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons

İrfan Çapan

Süleyman Servi

Abstract: Racemic dicarboxylic acids were synthesized from the Diels-Alder cycloaddition reactions which formed the dibenzobarrelene and norbornene skeletons. The pure enantiomers of these compounds were obtained using brucine as the chiral auxiliary. Novel C2-symmetric chiral benzimidazole derivatives were synthesized from the reaction of the diaminobenzene and the enantiomeric dicarboxylic acids in the presence of boric acid.

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Cited by 2 publications

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Synthesis and Anticancer Evaluation of Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons and Different Functional Groups

Çapan

Servi²,

Dalkılıç³

et al. 2020

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Two different anhydrides having norbornene and dibenzobarrelene skeletons were synthesized from Diels‐Alder cycloaddition reactions using dienes such as anthracene and cyclopentadiene, and dienophiles like maleic acid and maleic anhydride. New benzimidazole derivatives bearing carboxamide, guanidine, and cyclic imide functional groups were obtained from these anhydrides. The compounds were investigated for their effects on MDA‐MB‐231 (Human breast cancer), A549 (Lung cancer), Ovcar3 (Human Ovarian cancer), and Panc1 (human pancreas cancer) cell lines using the MTT assay test. Compounds 4–8 demonstrated critical cytotoxic action against all cell lines.

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Synthesis and Anticancer Evaluation of Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons and Different Functional Groups

Çapan

Servi²,

Dalkılıç³

et al. 2020

ChemistrySelect

Self Cite

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Synthesis, DFT Study, Molecular Docking and Drug‐Likeness Analysis of the New Hydrazine‐1‐Carbothioamide, Triazole and Thiadiazole Derivatives: Potential Inhibitors of HSP90

Çapan

Servi²,

Yıldırım

et al. 2021

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In this research, the new hydrazine-1-carbothioamides (IC32 and IC34) having unsubstituted benzimidazole skeleton were converted to 1, 2, 4-triazole derivatives (IC42 and IC44) by Ncyclization reaction using the microwave-assisted synthesis method in the basic medium with high efficiency in a short time. 2-Amino-1,3,4-thiadiazole derivatives (IC52 and IC54) were obtained from the carbothioamides in the acidic medium by S-cyclization using the conventional method. The structure of all compounds was confirmed by FT-IR, 1 H NMR, and 13 C NMR spectroscopic techniques. The optimized structures, theoretical NMR shielding values in DMSO-d 6 solvent, the frontier molecular orbital, molecular electrostatic potential, and non-linear optical properties of these molecules were calculated in the Gaussian 09 W package program by using DFT method/B3LYP function and 6-311 + + G (d, p) basis set. All calculations except NMR calculations were performed in the gas phase and the obtained results were interpreted within the related sections. The discovery of new drugs is of great importance in combating health problems and improving the quality of human life.In the light of this information, molecular docking with Autodock Vina and physicochemical calculations with the SwissADME server were performed at the end of the article. Therefore, the inhibiting potential of the ligands containing different groups in their structure was investigated for the first time in this study.

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Synthesis of New C2-Symmetric Chiral Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons

Cited by 2 publications

References 17 publications

Synthesis and Anticancer Evaluation of Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons and Different Functional Groups

Synthesis and Anticancer Evaluation of Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons and Different Functional Groups

Synthesis, DFT Study, Molecular Docking and Drug‐Likeness Analysis of the New Hydrazine‐1‐Carbothioamide, Triazole and Thiadiazole Derivatives: Potential Inhibitors of HSP90

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