کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
10267168 | 459445 | 2005 | 6 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Electrochemistry of β-lapachone and its diazoderivative: Relevance to their compared antimicrobial activities
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
مهندسی شیمی
مهندسی شیمی (عمومی)
پیش نمایش صفحه اول مقاله
![عکس صفحه اول مقاله: Electrochemistry of β-lapachone and its diazoderivative: Relevance to their compared antimicrobial activities Electrochemistry of β-lapachone and its diazoderivative: Relevance to their compared antimicrobial activities](/preview/png/10267168.png)
چکیده انگلیسی
A new diazo derivative (2) of β-lapachone (1) is synthesized in one step and good yield (72%). New and significant antimicrobial activity data toward several strains of resistant Staphylococcus aureus for β-lapachone are presented. For the new compound, compared with β-lapachone, the modification of the redox center decreased drastically the biological activity, a fact that could be rationalized by the electrochemical results. The redox properties of both compounds are investigated, in aprotic medium (DMF + 0.1 mol Lâ1 TBAP), using a glassy carbon electrode. For the diazoquinone, an unique irreversible monoelectronic reduction peak is observed. The reduction mechanism corresponds to an ECC process, where the first chemical reaction is the fast unimolecular loss of dinitrogen, leading to a transient carbene anion radical, which captures a hydrogen atom and furnishes a phenolate derivative. Addition of different proton sources (phenol, benzoic acid) does not affect at all the reduction wave, but leads to the disappearance of the corresponding anodic wave, due to the protonation of the phenolate anion. The reduction of 2 occurs at more negative potential and its anion radical is very short-lived, so this may be the main set of reasons, which prevents the generation of reactive oxygen species in situ and might be the reason for its lower antimicrobial activity.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Electrochemistry Communications - Volume 7, Issue 7, July 2005, Pages 767-772
Journal: Electrochemistry Communications - Volume 7, Issue 7, July 2005, Pages 767-772
نویسندگان
Fabiane C. de Abreu, Danielle C.M. Ferreira, Jay Wadhawan, Christian Amatore, Vitor F. Ferreira, Milton N. da Silva, Maria CecÃlia B.V. de Souza, Tatiana S. Gomes, Eulália Azevedo Ximenes, MarÃlia O.F. Goulart,