design and synthesis of 2-methyl and 2-methyl-4-nitro imidazole derivatives as antifungal agents

Authors

soghra khabnadideh

faculty of pharmacy and pharmaceutical sciences research center, shiraz university of medical sciences, shiraz, iran zahra rezaei

faculty of pharmacy and pharmaceutical sciences research center, shiraz university of medical sciences, shiraz, iran ali khalafi-nezhad

faculty of science, shiraz university, shiraz 71454, iran keyvan pakshir

department of parasitoligy and mycology, school of medicine, shiraz university of medical sciences, shiraz, iran mohammad javad heiran

abstract

two series (a and b) of n- substituted heteroaromatic compounds related to clotrimazole were synthesized. imidazole ring of the clotrimazole was replaced by 2-methylimidazole in series a, and by 2-methyl-4-nitroimidazole in series b. o-cholortrityl moiety of clotrimazole was also replaced by trityl, mono or dimethoxy trityl. chemical structures of all the new compounds were confirmed by spec-trophotometric methods. these compounds docked into the active site of mt-cyp51 (pdb code, 1e9x) using autodock tools software which showed good affinity for the enzyme. antifungal activities of these compounds were evaluated against trichophyton mentagrophytes, microsporum gypseum and candida albicans using sc, scc and pda as media, chcl3 and dmso as solvents and agar dilution assay as method. in this method 1(4-methoxyphenyl-diphenylmethyl)-2-methyl imidazole (2), 1[bis-4-methoxyphenyl-phenylmethyl]-2-methyl imidazole (3) and 1[4-methoxyphenyl-diphenylmethyl]-2-methyl-4-nitroimidazole (5) showed more than 75% activity against fungi. in the second step all of the derivatives also were evaluated against trichophyton rubrum, microsporum canis and epidermaphyton floccosum using pda medium by agar dilution method. compound 2 showed more than 75% activity by this method. then the most active analogue (2) was tested in rpmi 1640 medium which showed desirable biological activity in comparison to clotrimazole.

Upgrade to premium to download articles

Sign up to access the full text

Already have an account?login

similar resources

Design and Synthesis of 2-Methyl and 2-Methyl-4-Nitro Imidazole Derivatives as Antifungal Agents

      Two series (a and b) of N- substituted heteroaromatic compounds related to clotrimazole were synthesized. Imidazole ring of the clotrimazole was replaced by 2-methylimidazole in series a, and by 2-methyl-4-nitroimidazole in series b. O-cholortrityl moiety of clotrimazole was also replaced by trityl, mono or dimethoxy trityl. Chemical structures...

full text

Crystal structure of 1-methyl-2-[(E)-2-(4-methyl­phen­yl)ethen­yl]-4-nitro-1H-imidazole

In the title mol-ecule, C13H13N3O2, the planes of the benzene and imidazole rings form a dihedral angle of 7.72 (5)°. In the crystal, mol-ecules are linked by weak C-H⋯N and C-H⋯O hydrogen bonds, forming layers parallel to (100). A weak C-H⋯π inter-action connects these layers into a three-dimensional network. A π-π stacking inter-action, with a centroid-centroid distance of 3.5373 (9) Å, is al...

full text

Crystal structure of (E)-1-methyl-2-[2-(2-methoxphen­yl)ethen­yl]-4-nitro-1H-imidazole

In the asymmetric unit of the title compound, C13H13N3O3, the 2-(2-methoxphen-yl)ethenyl unit is connected to the methyl-nitro-imidazole 1-methyl-4-nitro-1H-imidazole moiety. The mol-ecule is quasi-planar and the planes of the two rings form a dihedral angle of 0.92 (11)°. The crystal packing can be described as layers parallel to the (011) plane, stabilized by inter-molecular C-H⋯O hydrogen bo...

full text

Novel Group of Imidazole Derivatives as Atypical Selective Cyclooxygenase-2 Inhibitors: Design, Synthesis and Biological Evaluation

In this study, a new series of 5-substituted 1-benzyl-2-(methylsulfonyl)-1-H-imidazolewith atypical structure-activity relationship was designed, synthesized, and biologicalevaluated as selective cyclooxygenase-2 inhibitors. Docking studies revealed that althoughthe pharmacophoric substitute of the compound 5b, methylsulfonyl group, has been directlyattached to the central ring, it is in the sa...

full text

Novel Group of Imidazole Derivatives as Atypical Selective Cyclooxygenase-2 Inhibitors: Design, Synthesis and Biological Evaluation

In this study, a new series of 5-substituted 1-benzyl-2-(methylsulfonyl)-1-H-imidazolewith atypical structure-activity relationship was designed, synthesized, and biologicalevaluated as selective cyclooxygenase-2 inhibitors. Docking studies revealed that althoughthe pharmacophoric substitute of the compound 5b, methylsulfonyl group, has been directlyattached to the central ring, it is in the sa...

full text

Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal Agents.

In this study two series of fluconazole derivatives bearing nitrotriazole (series A) or piperazine ethanol (series B) side chain were designed and synthesized and then docked in the active site of lanosterol 14α-demethylase enzyme (1EA1) using the Autodock 4.2 program (The scripps research institute, La Jolla, CA, USA). The structures of synthesized compound were confirmed by various methods in...

full text

My Resources

Save resource for easier access later


Journal title:
iranian journal of pharmaceutical sciences

جلد ۵، شماره ۱، صفحات ۳۱-۳۶

Keywords
[ ' a n t i f u n g a l a c t i v i t y ' , ' c l o t r i m a z o l e ' , 2 , ' m e t h y l i m i d a z o l e ' , 2 , ' m e t h y l ' , 4 , ' n i t r o i m i d a z o l e ' ]

Hosted on Doprax cloud platform doprax.com

copyright © 2015-2023