The synthesis of N-phenoxyethyl-1-substituted-1,2,3,4-tetrahydroisoquinolines and their alpha1-adrenoceptor blocking activity.
A series of phenoxyisoquinolines, N-phenoxyethyl-1-(2-nitrophenyl)-1,2,3,4-THIQs 3a-3d, N-phenoxyethyl-1-benzyl-1,2,3,4-THIQ 3e, N-phenoxyethyl-1-(2-aminophenyl)-1,2,3,4-THIQs 5f-5i, N-phenoxyethyl-1-(2-phenoxyethylaminophenyl)-1,2,3,4-THIQs 5f'-5i', have been synthesized and tested in isolated rat vas deferens alpha-adrenoreceptors. Comparison of pA2 values for these compounds in the presence of phenylephrine confirms that alpha(1)-adrenoceptor blocking activity of 3a-3d (-NO(2) series) is more active than 6a-6c (-NH(2) series) in the aortic rings isolated from SD rats. On the other hand, the electron-donating group at the 6-position of isoquinoline ring either increases or decreases the alpha(1)-adrenoceptor blocking activity.
Kuo
Chen-Yuan
CY
Department of Biological Engineering, Yung-Ta Institute of Technology and Commerce, 316 Jhong Shan Road, Pingtung 909, Taiwan, ROC. cykuo@mail.ytit.edu.tw
Wu
Ming-Jung
MJ
D058668:Adrenergic alpha-1 Receptor Antagonists; D000317:Adrenergic alpha-Antagonists / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D001011:Aorta / Q000187:drug effects; D066298:In Vitro Techniques; D008297:Male; D051381:Rats; D017207:Rats, Sprague-Dawley; D013329:Structure-Activity Relationship; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D014649:Vas Deferens / Q000187:drug effects
D058668:Adrenergic alpha-1 Receptor Antagonists; D000317:Adrenergic alpha-Antagonists; D044005:Tetrahydroisoquinolines; C014843:1,2,3,4-tetrahydroisoquinoline