Commenced in January 2007
Frequency: Monthly
Edition: International
Paper Count: 6

Search results for: oxadiazole

6 Exploitation of the Solvent Effect and the Mechanism of the Cycloaddition Reaction Between 2-Chlorobenzimidazole and Benzonitrile N-Oxide

Authors: M. Abdoul-Hakim, A. Zeroual, H. Garmes

Abstract:

2-Chlorobenzimidazoles are amphoteric compounds and versatile intermediates for the construction of polycyclic heterocycles. In this theoretical study performed by DFT at the B3LYP/6-311+G(d,p) level, we showed that the most likely route to obtain benzimidazo[1,2-d]oxadiazole from the reaction of 2-Chlorobenzimidazole with benzonitrile N-oxide involves the presence of anionic species, a concerted mechanism is not possible. The inclusion of the effect of the polar protic solvent (MeOH) favors the course of the reaction. The key interactions causing bond formation and breakage were identified by ELF topological analysis.

Keywords: benzimidazo[1, 2-d]oxadiazole, benzonitrile N-oxide, DFT, ELF, polycyclic heterocycles

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5 Quantitative Structure Activity Relationship and Insilco Docking of Substituted 1,3,4-Oxadiazole Derivatives as Potential Glucosamine-6-Phosphate Synthase Inhibitors

Authors: Suman Bala, Sunil Kamboj, Vipin Saini

Abstract:

Quantitative Structure Activity Relationship (QSAR) analysis has been developed to relate antifungal activity of novel substituted 1,3,4-oxadiazole against Candida albicans and Aspergillus niger using computer assisted multiple regression analysis. The study has shown the better relationship between antifungal activities with respect to various descriptors established by multiple regression analysis. The analysis has shown statistically significant correlation with R2 values 0.932 and 0.782 against Candida albicans and Aspergillus niger respectively. These derivatives were further subjected to molecular docking studies to investigate the interactions between the target compounds and amino acid residues present in the active site of glucosamine-6-phosphate synthase. All the synthesized compounds have better docking score as compared to standard fluconazole. Our results could be used for the further design as well as development of optimal and potential antifungal agents.

Keywords: 1, 3, 4-oxadiazole, QSAR, multiple linear regression, docking, glucosamine-6-phosphate synthase

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4 Design and Synthesis of Some Oxadiazole Bearing Benzimidazole Derivatives as Potential Epidermal Growth Factor Receptor Inhibitors

Authors: Ismail Celik, Gulgun Ayhan Kilcigil, Berna Guven, Zumra Kara, Arzu Onay-Besikci

Abstract:

Epidermal Growth Factor Receptor is the cell-surface receptor of the ErbB (erythroblastic leukemia viral oncogene homologue receptors) family of tyrosine kinases. It plays a vital role in regulating the proliferation and differentiation of cells. However, a variety of mechanisms, such as EGFR expression, mutation, and ligand-dependent receptor dimerization, are associated with the development of various activated EGFR tumors. EGFR is highly expressed in most solid tumors, including breast, head and neck cancer, non-small cell lung cancer (NSCLC), renal, ovarian, and colon cancers. Thus, specific EGFR inhibition plays one of the key roles in cancer treatment. The compounds used in the treatment as tyrosine kinase inhibitors are known to contain the benzimidazole isosterium indole, pazopanib, and axitinibin indazole rings. In addition, benzimidazoles have been shown to exhibit protein kinase inhibitory activity in addition to their different biological activities.Based on these data, it was planned and synthesized of some oxadiazole bearing benzimidazole derivatives [N-cyclohexyl-5-((2-phenyl/substitutedphenyl-1H-benzo[d]imidazole-1-yl) methyl)-1,3,4-oxadiazole-2-amine]. EGFR kinase inhibitory efficiency of the synthesized compounds was determined by comparing them with a known kinase inhibitor erlotinib in vitro, and two of the compounds bearing phenyl (19a) and 3,4-dibenzyloxyphenyl (21a) ring exhibited significant activities.

Keywords: benzimidazole, EGFR kinase inhibitory, oxadiazole, synthesis

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3 Discerning of Antimicrobial Potential of Phenylpropanoic Acid Derived Oxadiazoles

Authors: Neeraj Kumar Fuloria, Shivkanya Fuloria, Amit Singh

Abstract:

2-Phenyl propionic acid and oxadiazoles possess antimicrobial potential. 2-Phenyl propane hydrazide (1), on cyclization with aromatic acids offered 2-aryl-5-(1-phenylethyl)-1,3,4-oxadiazole derivatives (1A-E). The PPA derived oxadiazoles were characterized by elemental analysis and spectral studies. The compounds were screened for antimicrobial potential. The compound 1D bearing strong electron withdrawing group showed maximum antimicrobial potential. Other compounds also displayed antimicrobial potential to a certain extent. The SAR of newer oxadiazoles indicated that substitution of strong electronegative group in the PPA derived oxadiazoles enhanced their antimicrobial potential.

Keywords: antimicrobial, imines, oxadiazoles, PPA

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2 Synthesis and Antimicrobial Activity of Tolyloxy Derived Oxadiazoles

Authors: Shivkanya Fuloria, Neeraj Kumar Fuloria, Sokinder Kumar

Abstract:

m-Cresol and oxadiazoles are the potent antimicrobial moieties. 2-(m-Tolyloxy)acetohydrazide (1) on cyclization with aromatic acids yielded 2-(aryl)-5-(m-tolyloxymethyl)-1,3,4-oxadiazole (1A-E). The structures of newer oxadiazoles were confirmed by elemental and spectral analysis. The newer compounds were evaluated for their antimicrobial potential. The compound 1E containing strong electron withdrawing group showed maximum antimicrobial potential. Other compounds also displayed antimicrobial potential to certain extent. The SAR of newer oxadiazoles indicated that substitution of strong electronegative group in the tolyloxy derived oxadiazoles enhanced their antimicrobial potential.

Keywords: antibacterial, cresol, hydrazide, oxadiazoles

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1 Synthesis and Biological Evaluation of Pyridine Derivatives as Antimicrobial Agents

Authors: Dagim Ali Hussen, Adnan A. Bekhit, Ariaya Hymete

Abstract:

In this study, several pyridine derivatives were synthesized and evaluated for their in vitro antimicrobial activity against gram-positive bacteria (S. aureus and B. Cereus), gram-negative bacteria (P. aeruginosa and E. coli) and fungus (C. albican and A niger). The intermediate chalcone derivative 2a,b was synthesized by condensation of pyrazole aldehydes 1a,b with acetophenone in alcoholic KOH. Cyclization of 2a,b with ethyl cyanoacetate ad ammonium acetate resulted in pyridine carbonitrile derivatives 3a,b. Furthermore, condensation of pyridine-4-carboxaldeyhe with different amino-derivatives gave rise to pyridine derivatives 5a,b, 6a,b. The oxadiazole derivative 7a was prepared by cyclization of 6a with acetic anhydride. Characterization of the synthesized compound was performed using IR, 1H NMR, 13C NMR spectra and elemental microanalyses. The antimicrobial results revealed that compounds 5a, 6b and 7a exhibited half fold antibacterial activity compared to ampicillin, against B. cereus. On the other hand, compound 3b showed an equivalent activity compared to miconazole against candida albican (CANDAL 03) and to clotrimazole against the clinical isolate candida albican 6647. Moreover, this compound 3b was further tested for its acute toxicity profile. The results showed that oral LD50 is more that 300 mg/kg and parentral LD50 is more than 100 mg/kg. Compound 3b is a good candidate for antifungal agent with good toxicity profile, and deserves more chemical derivatization and clinical study.

Keywords: antifungal, antimicrobial, Candida albican, pyridine

Procedia PDF Downloads 425