（E）-9-和（E）-10-硝基十八碳-9-烯酸的区域和立体特异性合成及其一氧化氮供体性质
Regio- and stereospecific syntheses and nitric oxide donor properties of (E)-9- and (E)-10-nitrooctadec-9-enoic acids.
作者信息
Gorczynski Michael J, Huang Jinming, King S Bruce
机构信息
Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
出版信息
Org Lett. 2006 May 25;8(11):2305-8. doi: 10.1021/ol060548w.
Abstract
[reaction: see text] Nitrated fatty acids act as endogenous peroxisome proliferator-activated receptor gamma (PPARgamma) ligands and nitric oxide (NO) donors. We describe the first specific preparation of the two regioisomers of nitrooleic acid, (E)-9-nitrooctadec-9-enoic acid (1) and (E)-10-nitrooctadec-9-enoic acid (2), from cis-cyclooctene and monomethyl azelate, respectively. These syntheses rely upon a Henry condensation between a nine-carbon nitro component and a nine-carbon aldehyde. Preliminary chemiluminescence NO detection studies reveal the ability of these nitrated fatty acids to release NO.
摘要
[反应：见正文] 硝化脂肪酸作为内源性过氧化物酶体增殖物激活受体γ（PPARγ）配体和一氧化氮（NO）供体。我们分别描述了从顺式环辛烯和壬二酸单甲酯首次特异性制备硝基油酸的两种区域异构体，即（E）-9-硝基十八碳-9-烯酸（1）和（E）-10-硝基十八碳-9-烯酸（2）。这些合成方法依赖于九碳硝基组分与九碳醛之间的亨利缩合反应。初步的化学发光NO检测研究揭示了这些硝化脂肪酸释放NO的能力。
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