design and synthesis of 2-methyl and 2-methyl-4-nitro imidazole derivatives as antifungal agents
Authors
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.
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 textCrystal 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 textCrystal 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 textNovel 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 textNovel 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 textDesign, 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 textMy Resources
Save resource for easier access later
Journal title:
iranian journal of pharmaceutical sciencesجلد ۵، شماره ۱، صفحات ۳۱-۳۶
Hosted on Doprax cloud platform doprax.com
copyright © 2015-2023