Abstract

Synthesis, characterization, and anti-Candida activity of ({(E)-[3-(1H-imidazol-1-yl)-1-phenylpropylidene]amino}oxy)(4-nitrophenyl)methanone (4) are reported. Compound 4 showed anti-Candida albicans activity (MIC = 0.6862 µmol/mL) being nearly 5-fold more potent than the gold standard antifungal drug, fluconazole (MIC ˃ 3.265 µmol/mL), on the clinical isolates of Candida albicans. Single crystal X-ray structure of the title compound 4 confirmed its assigned (E)-configuration. The compound crystallizes in the triclinic, P-1 (no. 2), a = 6.4633 (1) Å, b = 11.1063 (2) Å, c = 12.9872 (2) Å, α = 67.650 (1)°, β = 86.415 (1)°, γ = 86.776 (1)°, V = 860.01 (3)Å3, Z = 2, R(F) = 0.046, wR(F2) = 0.139, T = 296 K. The crystal structure is stabilized by weak intermolecular C—H•••O hydrogen interactions.

Highlights

  • IntroductionThe incidence of serious fungal infections has significantly increased

  • In recent years, the incidence of serious fungal infections has significantly increased

  • Candida albicans is the most common pathogen in invasive candidiasis, non-albicans Candida species have become more prevalent as agents of infection (Groll and Walsh, 2001; Singh, 2001; Slavin, 2002)

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Summary

Introduction

The incidence of serious fungal infections has significantly increased. Such infections are mainly affecting immunocomprimized patients associated with AIDS, organ transplantation, cancer chemotherapy and those using invasive devices, such as such as urinary catheters (Hossain and Ghannoum, 2000). In order to overcome these serious problems, the development of new antifungal agents has gained great importance (Ghannoum and Rice, 1999; Kathiravan et al, 2012; Moellering, 2011; Pfaller and Diekema, 2007; Sun et al, 2007). The epidemiological trends have emphasized the increasing importance of the infections caused by resistant fungal species to azoles (Canuto and Rodero, 2002)

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