کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1372077 | 981865 | 2010 | 4 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Synthesis and hSERT activity of homotryptamine analogs. Part 6: [3+2] dipolar cycloaddition of 3-vinylindoles Synthesis and hSERT activity of homotryptamine analogs. Part 6: [3+2] dipolar cycloaddition of 3-vinylindoles](/preview/png/1372077.png)
Substituted 1-tosyl-3-vinylindoles undergo [3+2] dipolar cycloaddition with cyclic nitrones to afford substituted isoxazoles in good yield and high diastereoselectivity. The cycloadducts were readily converted in 4 steps into ring constrained homotryptamine analogs. These analogs exhibited excellent binding affinity for the human serotonin transporter (hSERT). Indoles bearing a 5-cyano group and a pendent ethyl(tetrahydroisoquinoline) moiety at the 3-position displayed the best potency for hSERT and high selectivity versus hDAT and hNET.
A series of ring constrained homotryptamine analogs was prepared in 5 steps from 1-tosyl-3-vinylindoles via [3+2] dipolar cycloaddition with cyclic nitrones. The final products, including (−)-21a, demonstrated potent and selective binding affinity for the human serotonin transporter (hSERT).Figure optionsDownload as PowerPoint slide
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 20, Issue 3, 1 February 2010, Pages 1027–1030