Improved synthesis of (5Z)-7-(3-endo-{(benzenesulfonamido)-bicyclo[2.2.1]heptyl}hept-5-enoic acid (S-145) derivatives and their iodine-125-labeled radioligands for the study of thromboxane A2 receptor

Ming Kan Wai Ming Kan, Hsin Hsiung Tai

研究成果: Article同行評審

2 引文 斯高帕斯(Scopus)

摘要

An improved synthetic scheme for (5Z)-7-{3-endo-[(benzenesulfonamido)-bicyclo[2.2.1]heptyl}-hept-5-enoic acid (S145) and its analogs has been designed. The procedure involves direct sulfonylation of 2-allyl-3-aminobicyclo[2.2.1]heptane intermediate followed by ozonolysis and addition of a C5 carboxyl unit. The yield of the final product was significantly improved. (5Z)-7-{3-endo-[(4-iodobenzensulfonamido)-bicyclo [2.2.1]heptyl}hept-5-enoic acid (HS-145) and (5Z)-7-{3-endo-[(4-hydroxy-benzensulfonamido)-bicyclo [2.2.1]heptyl}hept-5-enoic acid (HS-145) were synthesized directly without any protection and deprotection steps. [125I](5Z)-7-{3-endo-[(4-iodobenzensulfonamido)- bicyclo[2.2.1]heptyl}hept-5-enoic acid ([125I]HS-145) was prepared from IS-145 through an organotin intermediate and [125I]sodium iodide with high specific radioactivity and good recovery of radioactivity. [125I](5Z)-7-{3-endo-[(4-hydroxy 3-iodo-benzensulfonamido)-bicyclo[2.2.1]-heptyl}hept-5-enoic acid ([125I]HS-145) was prepared by direct iodination with sodium iodide using a modified chloramine-T method. Both [125]HS-145 and [125I]HS-145 were found to be valuable radioligands for studying thromboxane A2 (TXA2) receptor.

原文English
頁(從 - 到)57-64
頁數8
期刊Chemistry and Physics of Lipids
65
發行號1
DOIs
出版狀態Published - 1993 4月

All Science Journal Classification (ASJC) codes

  • 生物化學
  • 分子生物學
  • 有機化學
  • 細胞生物學

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