Synthesis of New Substituted 4,5-Dihydro-3H-spiro[1,5]-benzoxazepine-2,4′-piperidine and Biological Properties

Younes Laras; Nicolas Pietrancosta; Vincent Moret; Sylvain Marc; Cédrik Garino; Amandine Rolland; Valérie Monnier; Jean-Louis Kraus

doi:10.1071/CH06318

RESEARCH ARTICLE

Synthesis of New Substituted 4,5-Dihydro-3H-spiro[1,5]-benzoxazepine-2,4′-piperidine and Biological Properties

Younes Laras ^A , Nicolas Pietrancosta ^A , Vincent Moret ^A , Sylvain Marc ^A , Cédrik Garino ^A , Amandine Rolland ^A , Valérie Monnier ^B and Jean-Louis Kraus ^A ^C

+ Author Affiliations

- Author Affiliations

^A Laboratoire de Chimie Biomoléculaire, IBDML Faculté des Sciences de Luminy, Université de la Méditerranée, 13288 Marseille Cedex 9, France.

^B Spectropole-Service de Spectrométrie de Masse, Faculté de St Jérôme, Avenue Escadrille Normandie Niémen, 13397 Marseille Cedex 20, France.

^C Corresponding author. Email: kraus@luminy.univ-mrs.fr

Australian Journal of Chemistry 59(11) 812-818 https://doi.org/10.1071/CH06318
Submitted: 30 August 2006 Accepted: 9 October 2006 Published: 17 November 2006

Abstract

The reduction of substituted spiro-piperidinyl chromanone oximes with DIBAH reagents has been known to afford the corresponding substituted 4,5-dihydro-3H-spiro[1,5]-benzoxazepine-2,4′-piperidine. The position and electronic effects of the substituents on the aryl moiety control the observed rearrangement. Spiro-benzoxazepine analogue 5j represents a key intermediate for the creation of a library of diverse potential bioactive drugs. With three functional groups that could be selectively and orthogonally protected, many different substituents can be introduced. The obtained analogues were assayed as the possible aspartyl protease inhibitors HIV protease (HIV-1), and β-secretase (BACE-1).

Acknowledgment

Professor K. Dudley is greatly acknowledged for assistance with manuscript preparation.

References

Synthesis of New Substituted 4,5-Dihydro-3H-spiro[1,5]-benzoxazepine-2,4′-piperidine and Biological Properties

Abstract

Acknowledgment

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