کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1397564 1501178 2011 9 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Carbaboranes as pharmacophores: Similarities and differences between aspirin and asborin
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Carbaboranes as pharmacophores: Similarities and differences between aspirin and asborin
چکیده انگلیسی

In medicinal chemistry carbaboranes have been used almost exclusively as boron carriers for boron neutron capture therapy (BNCT). Recent developments extended the carrier approach and use carbaboranes as scaffolds for radiodiagnostic or therapeutic agents. Most recent studies, however, focus on carbaboranes as modern hydrophobic pharmacophores. This research employs preferably meta- and para-carbaborane, because these isomers are extremely hydrophobic and very stable. In this paper we therefore investigated the pharmacophoric behavior of the ortho isomer as putative phenyl mimetic by comparing aspirin to asborin, its ortho-carbaborane analogue. Special emphasis is placed on the impact of the cluster properties on the pharmacological profile. Subjects under study are the mode of cyclooxygenase (COX) inhibition, stability, and toxicity. The straightforward syntheses of the corresponding nido compounds as well as their contribution to the pharmacology of the closo precursors will be highlighted. Finally, proof will be given that the ortho-carbaborane core of asborin merits the designation “pharmacophore” by definition and is a multifunctional group rather than just a hydrophobic, bulky spectator.

Figure optionsDownload as PowerPoint slideResearch highlights
► Carbaboranes are used as modern hydrophobic pharmacophores.
► Comparison of aspirin to asborin, its ortho-carbaborane analogue, in mode of cyclooxygenase (COX) inhibition, stability, and toxicity.
► Syntheses of the corresponding nido compounds and their contribution to the pharmacology of the closo precursors are highlighted.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: European Journal of Medicinal Chemistry - Volume 46, Issue 4, April 2011, Pages 1131–1139
نویسندگان
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