Synthesis, Crystal Structure, Electrochemical Properties, and Biological Activity of 2-((1H-Benzimidazol-2-yl)methylamin
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TRUCTURE OF MACROMOLECULAR COMPOUNDS
Synthesis, Crystal Structure, Electrochemical Properties, and Biological Activity of 2-((1H-Benzimidazol-2-yl)methylamino)acetic Acid1 T. Sabithakalaa, G. Bhargavib, and Ch. Venkata Ramana Reddya,* a
Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, Hyderabad, 500085 India bSchool of Chemistry, University of Hyderabad, Hyderabad, 500046 India *e-mail: [email protected] Received March 23, 2017
Abstract—A water soluble compound, (2-((1H-benzimidazol-2-yl)methylamino)acetic acid, BIGH, has been synthesized and structurally characterized by elemental analysis, IR and UV spectroscopies, 1H-NMR, thermogravimetric and differential thermal analyses, and single crystal and powder X-ray diffraction. BIGH can act as a flexible planar ligand with three potential coordination sites. It crystallizes in a monoclinic system with the sp. gr. P21/c with the unit cell parameters, a = 9.3764(7) Å, b = 11.5031(8) Å, c = 10.0543(6) Å, and Z = 4. The crystal structure was stabilized through inter-molecular hydrogen bonds. The anti-microbial activity of the compound has been studied against Escherichia coli, Bacillus subtilis, Pseudomonas aeruginosa, and Staphylococcus aureus, which showed a good activity against Bacillus subtilis. Cyclic voltammogram of the compound shows that it is a redox-active molecule. DOI: 10.1134/S1063774518040235
INTRODUCTION Benzimidazole is an important nitrogen heterocycle. Its derivatives provide building blocks for structural variability and also show pharmacological activities. The discovery of 5,6-dimethyl-1-(α-D-ribofuranosyl)benzimidazole [1] as a basic unit of the vitamine-B12 led to massive research in synthesis new benzimidazole derivatives. Benzimidazole derivatives are also useful intermediates for the development of new chemical entities and molecules of potential biological interest [2, 3]. In addition to the benzimidazole moiety, amino acids are also found to be an important pharmacophore in medicinal chemistry. Due to their favorable spatial and cationic properties, amino acids are also included in our target compound. 2-Substituted benzimidazoles show a wide range of biological activities [4–11] including antiulcer, antihypertensive, antiviral, antifungal, anticancer, and antihistaminic. The widespread interest [12] in benzimidazole and substituted amino acids has prompted us for the synthesis of 2-((1H-benzimidazol-2-yl)methylamino)acetic acid, BIGH, by an alternative method which can pave way for the synthesis of many other amino acid coupled benzimidazole derivatives. Further, benzimidazole, amino acid derivative also has the added benefit of providing steric bulk in the vicinity of the metal due to 1 The article is published in the original.
the presence of arene ring in the structure as potential chelating agents with biological activity [13]. EXPERIMENTAL Materials and Methods The chemicals used, Chloroacetic acid (Aldrich), orthophenelinediamine (OPDA) (Aldrich), hydrochloric acid (Merck), aqueous ammonia (Aldrich), potas
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