Romanian Society of Pharmaceutical Sciences
 

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SYNTHESIS OF BENZIMIDAZOLES IN THE PRESENCE OF NANO-TiCl4.SiO2 AS ANTIFUNGAL AGENTS AND TAUTOMERISM THEORETICAL STUDY OF SOME PRODUCTS

LEILA ZAMANI1, BI BI FATEMEH MIRJALILI1, KAMIAR ZOMORODIAN2*, MANSOOR NAMAZIAN1, SOGHRA KHABNADIDEH3, EHSAN FAGHIH MIRZAEI3,4

1.Department of Chemistry, College of Science, Yazd University, Yazd, P.O. Box 8915813149, Iran.
2 .Center of Basic Researches in Infectious Diseases and Department of Medical Mycology and Parasitology School of Medicine, Shiraz University of Medical Sciences, Post code 71348-45794, Shiraz, Iran
3 .Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical S.ciences, Shiraz, I. R. Iran.
4 .Department of Medicinal Chemistry, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, Iran

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Pathogenic fungi are associated with diseases ranging from simple dermatosis to life-threatening infections, particularly in immunocompromised patients. During the past two decades, resistance to established antifungal drugs has increased dramatically and has become extremely important to identify novel antimicrobial compounds. The purpose of this study was to synthesize some new benzimidazole derivatives and to evaluate their activity against some species of Candida, Aspergillus and dermatophytes. Benzimidazoles have been synthesized in the presence of nano-TiCl4.SiO2 as a reusable and efficient catalyst. The stability of different tautomers of some products has been investigated using standard ab initio calculations. The antimicrobial activities of the synthetic compounds have been tested against the fungi by Broth microdilution method as recommended by Clinical and Laboratory Standards Institute (CLSI). Inhibition studies showed that some of the tested compounds, in particular 2-(2,3-dihydroxyphenyl)-1H-5-Nitro-benzimidazole exhibited strong antifungal activities against all tested fungi at concentrations of less than 32 μg/mL while some of them only inhibited the growth of dermatophytes or Aspergillus species. These results suggest that the derivatives should be further investigated for possible use in antimicrobial products.