期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 7, 页码 3844-3854出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00440
关键词
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资金
- National Institutes of Health [AI105084]
2-Alkyl-1,2-benzisoselenazol-3(2H)-ones, represented by ebselen (la), are being studied intensively for a range of medicinal applications. We describe both a new thermal and photoinduced copper-mediated cross-coupling between potassium selenocyanate (KSeCN) and N-substituted ortho-halobenzamides to form 2-alkyl-1,2-benzisoselenazol-3(2H)-ones containing a C-Se-N bond. The copper ligand (1,10-phenanthroline) facilitates C Se bond formation during heating via a mechanism that likely involves atom transfer (AT), whereas, in the absence of ligand, photoinduced activation likely proceeds through a single electron transfer (SET) mechanism. A library of 15 2-alkyl-1,2-benzisoselenazol-3(2H)-ones was prepared. One member of the library was azide-containing derivative lj that was competent to undergo a strain-promoted azide alkyne cycloaddition. The library was evaluated for inhibition of Mycobacterium tuberculosis (Mtb) growth and Mtb Antigen 85C (Mtb Ag85C) activity. Compound if was most potent with a minimal inhibitory' concentration (MIC) of 12.5 ftg/mL and an Mtb Ag85C apparent IC50 of 8.8 mu M.
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