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Synthesis of a new azapeptide with renin‐inhibiting properties
Author(s) -
Gante Joachim,
Weitzel Reinhard
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900166
Subject(s) - chemistry , carbodiimide , hydrazine (antidepressant) , chloroformate , renin inhibitor , ethyl chloroformate , stereochemistry , renin–angiotensin system , oligopeptide , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , peptide , medicine , blood pressure , radiology
Boc‐hydrazine ( 1 ) was treated with 4‐nitrophenyl chloroformate ( 2 ) to give Boc‐Azagly 4‐nitrophenyl ester ( 3 ). Reaction of 3 with H‐ACHP‐Ile‐3‐pyridylmethylamide 5) ( 4 ) provided Boc‐Azagly‐ACHP‐Ile‐3‐pyridylmethylamide ( 5 ). This was deprotected with HCl/dioxane to give H‐Azagly‐ACHP‐Ile‐3‐pyridylmethylamide dihydrochloride ( 6 ), which was coupled with Boc‐Phe‐OH ( 7 ) by the carbodiimide/HOBt method providing the final azapeptide Boc‐Phe‐Azagly‐ACHP‐3‐pyridyl‐methylamide ( 8 ). This compound was shown to be a renin inhibitor of high specificity.