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Synthesis of 1‐(2‐Carboxyethylbenzyl)‐2‐benzenesulfonamidobicyclo[2.2.1]heptane: A Novel Potent Thromboxane Antagonist
Author(s) -
Kan WaiMing,
Chem ChingYuh,
Su ShengFang
Publication year - 1998
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199800107
Subject(s) - chemistry , antagonist , heptane , ether , thromboxane , prostaglandin , tetrahydropyran , thromboxane a2 , stereochemistry , thromboxane receptor , platelet aggregation , pharmacology , receptor , platelet , biochemistry , ring (chemistry) , organic chemistry , medicine
A potent thromboxane antagonist, 1‐[2‐(2‐carboxyethyl)benzyl)]‐2‐benzenesulfonamidobicyclo‐[2.2.1]heptane was synthesized from norcamphor in 8 steps. It was shown to be a very potent thromboxane antagonist by inhibition of platelet aggregation induced by U46,619 at nanomolar concentration. The key intermediate 3‐[2‐bromomethylphenyl]propyl tetrahydropyran ether may be useful for the synthesis of other interphenylene containing prostaglandin analogs.