SYNTHESIS OF 9-AMINO-6,7-BENZOMORPHAN AS A POTENTIAL ANALGESIC

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Date
1987-11
Authors
TOR-ANYIIN, TERRUMUN AMOM
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Abstract
6,7-Benzomorphans have been reported to show pronounce n a r c o t i c analgesic activities. In proceeding years several compounds comprising 6,7-benzomorphan nucleus have been synthesized. Previous works were c e n t r e d mainly on structure- activity relationship to the effective of oxygen, hydroxide, alkyd or aryl s u b s t i t u e n t s on various p o s i t i o n s of the molecule and v a r i a t i o n of N - s u b s t i t u e n t s . The present work is concerned with t h e synthesis of 6,7-benzomorphan having an amino group at C-9 of the molecule. The s y n t h e s i s of the t i t l e compound involved bromination and rearrangement of h e t e r o c y c l i c enamines, followed by aqueous basic hydrolysis to give 9-oxobenzomorphan. Conversion of 9-oxo compound to the oxime followed by c a t a l y t i c reduction afforded the desired 9o(-amino-6,7-benzomorphan. Its pharmacology demonstrated a dose-dependent i n h i b i t i o n analgesia. The product obtained as well as the intermediates have been analyzed and c h a r a c t e r i z e d on the basis of thier spectrial and chemical properties
Description
A THESIS SUBMITTED TO THE POSTGRADUATE SCHOOL, AHMADU BELLO UNIVERSITY, IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE IN PHARMACEUTICAL CHEMISTRY DEPARTMENT OF PHARMACEUTICAL AND MEDICINAL CHEMISTRY FACULTY OF PHARMACEUTICAL SCIENCES AHMADU BELLO UNIVERSITY ZARIA, NIGERIA NOVEMBER, 1987
Keywords
SYNTHESIS,, 9-AMINO-6,7,, -BENZOMORPHAN,, POTENTIAL,, ANALGESIC
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