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.
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.
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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