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
1Department of Chemistry, College of Science, Yazd University, Yazd, P.
O. Box 8915813149, Iran.
2Center 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
3Department of Medicinal Chemistry, Faculty of Pharmacy and
Pharmaceutical Sciences Research Center, Shiraz University of Medical
Sciences, Shiraz, I. R. Iran.
4Department of Medicinal Chemistry, Faculty of Pharmacy, Kerman
University of Medical Sciences, Kerman, Iran
* corresponding author: zomorodian@sums.ac.ir, zomorodian2@yahoo.com
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Abstract:

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.

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