Design and synthesis of novel imidazole derivatives as potent inhibitors of allene oxide synthase(CYP74)
Allene oxide synthase (AOS) is a key enzyme in the oxylipin pathway in plants leading to jasmonic acid and other jasmonates (JAs), important signal mediators of defense signal networks in plants. AOS uses hydroperoxylinolenic acid as an oxygen donor as we
Aliphatic ethers of 1-(2,4-dichlorophenyl)-2-(1-H-imidazolyl)ethanol: Influence of ramification and/or unsaturation on lipophilicity and antifungal activity
Ethers of 1-(2,4-dichlorophenyl)-2-(1-H-imidazolyl)ethanol bearing influence ramification and/or unsaturated chains have been synthesized in order to specify the role of lipophilicity or steric contributions on antifungal activity against yeast for miconazole-like structures. The presence of ramifications on aliphatic chains (between 4 and 7 carbons) or unsaturation at the end, increases antifungal activity. For these compounds, lipophilicity seems to be counterbalanced by steric contributions.
Structure-activity relationships of a new antifungal imidazole, AFK-108, and related compounds
Fungicidal activity of widely used imidazole antifungal drugs in topical applications is not so strong in spite of their potent fungistatic activities against dermatophytes and pathogenic yeasts. In order to improve fungicidal activity of imidazole antifungal agents, a series of novel imidazole derivatives having a hydrophobic substituent derived from isoprenoid were synthesized. The efficacy of these compounds was evaluated with respect to direct cell-membrane damaging activity, ergosterol biosynthesis inhibition, minimum growth-inhibitory concentration (MIC) and therapeutic effect for experimental dermatophytosis of guinea pigs. Among the newly synthesized compounds, the geranyl derivative named AFK-108 (2a) showed the highest in vivo fungicidal activity with both cell membrane damaging activity and ergosterol biosynthesis inhibition in vitro.
Hori, Kimihiko,Sakaguchi, Akira,Kudoh, Michinari,Ishida, Koichi,Aoyama, Yuri,Yoshida, Yuzo
p. 60 - 64
(2007/10/03)
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