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

Wai-Ming Kan, Hsin Hsiung Tai

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2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)57-64
Number of pages8
JournalChemistry and Physics of Lipids
Volume65
Issue number1
DOIs
Publication statusPublished - 1993 Jan 1

Fingerprint

S 145
Prostaglandin H2 Receptors Thromboxane A2
Iodine
Derivatives
Acids
Sodium Iodide
Radioactivity
Heptanes
Halogenation
Recovery

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Biophysics

Cite this

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title = "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",
abstract = "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.",
author = "Wai-Ming Kan and Tai, {Hsin Hsiung}",
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T1 - 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

AU - Kan, Wai-Ming

AU - Tai, Hsin Hsiung

PY - 1993/1/1

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N2 - 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.

AB - 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.

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