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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.
Kan, W M; Tai, H H.
Afiliação
  • Kan WM; Division of Medicinal Chemistry and Pharmaceutics, College of Pharmacy, University of Kentucky, Lexington 40536-0082.
Chem Phys Lipids ; 65(1): 57-64, 1993 Apr.
Article em En | MEDLINE | ID: mdl-8348677
ABSTRACT
An improved synthetic scheme for (5Z)-7-(3-endo-[(benzenesulfonamido)-bicyclo[2.2.1]heptyl)-h ept-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-iodobenzenesulfonamido)-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-benzenesulfonamido)-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 [125I]HS-145 and [125I]HS-145 were found to be valuable radioligands for studying thromboxane A2 (TXA2) receptor.
Assuntos
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Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Compostos Bicíclicos com Pontes / Ácidos Graxos Monoinsaturados / Receptores de Tromboxanos Limite: Humans Idioma: En Revista: Chem Phys Lipids Ano de publicação: 1993 Tipo de documento: Article
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Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Compostos Bicíclicos com Pontes / Ácidos Graxos Monoinsaturados / Receptores de Tromboxanos Limite: Humans Idioma: En Revista: Chem Phys Lipids Ano de publicação: 1993 Tipo de documento: Article