Long-Acting Angiotensin II Inhibitors Containing Hexafluorovaline in Position 8

Kun Hwa Hsieh, Philip Needleman, Garland R. Marshall

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

An improved synthesis of hexafluorovaline (Hfv) derivatives, i.e., DL-Hfv-OBzl and Boc-DL-Hfv, is described. Incorporation of hexafluorovaline into angiotensin resulted in [Sar1,Hfv8]AII and [Sar1,D-Hfv8] AII. At the nanogram/milliliter dose range, the L congener was 20–100 times more active as either angiotensin agonist or angiotensin antagonist than its D diastereomer on isolated tissue preparations. At the microgram dose range, both [Sar1,Hfv8]AII and [Sar1,D-Hfv8]AII were significantly more effective than [Sar1,Leu8]AII as angiotensin II inhibitors, producing prolonged blockade of the pressor response toward angiotensin II for over 1 h.

Original languageEnglish
Pages (from-to)1097-1100
Number of pages4
JournalJournal of Medicinal Chemistry
Volume30
Issue number6
DOIs
StatePublished - Jun 1 1987

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