Enzyme inhibitors XXIII: Syntheses of 9‐(substituted aralkyl)‐6‐substituted purines as inhibitors of adenosine deaminase

Howard J. Schaeffer, Eugene Odin, Shmuel Bittner

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

A series of 9‐(substituted aralkyl)‐6‐substituted purines was prepared as potential inhibitors of adenosine deaminase. The adenine derivatives were reversible inhibitors of adenosine deaminase, with potencies not strikingly different than the corresponding benzyl derivatives. However, 9‐(p‐bromoacetamidophenethyl)‐adenine (XV) and 9‐(3‐o‐ and p‐bromoacetamidophenylpropyl)‐adenines (XXIXa and XXIXb) were incapable of causing irreversible inhibition of adenosine deaminase, whereas the corresponding ortho‐ and para‐benzyl derivatives (I and II) and 9‐(m‐bromoacetamidophenethyl)adenine (IV) caused rapid irreversible inactivation of this enzyme. These experiments demonstrated the selectivity of irreversible inhibition that can be obtained by site‐directed irreversible enzyme inhibitors.

Original languageEnglish
Pages (from-to)1184-1188
Number of pages5
JournalJournal of Pharmaceutical Sciences
Volume60
Issue number8
DOIs
StatePublished - 1 Jan 1971
Externally publishedYes

Keywords

  • Adenosine deaminase inhibitors, irreversible—9‐(substituted aralkyl)‐6‐substituted purines
  • Enzymes, irreversible site‐directed inhibitors—9‐(substituted aralkyl)‐6‐substituted purines
  • Purines, 9‐(substituted aralkyl)‐6‐substituted—syntheses, adenosine deaminase irreversible inhibitors

ASJC Scopus subject areas

  • Pharmaceutical Science

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