Date of Award

Summer 1987

Document Type


Degree Name

Master of Science (MS)


Chemistry & Biochemistry



Committee Director

Roy L. Williams

Committee Member

Patricia B. Williams

Committee Member

Frank E. Scully, Jr.

Committee Member

John D. Van Norman

Call Number for Print

Special Collections LD4331.C45C47


An investigation was undertaken to synthesize and evaluate longer acting analogs to the antihypertensive agent nifedipine. Analogs that are capable of covalent bonding to the nifedipine receptor were considered. These compounds may show increased activity as they will remain at the receptor for a longer period of time.

During the course of this study, previously unreported and unexpected products were encountered and lead to a more intense examination of the Hantzsch synthesis. Of particular interest was the oxazolidine 25 which was a major component of the Hantzsch synthesis when ethanolamine was used instead of ammonium hydroxide. Also isolated during this reaction were two alternate cyclization products 35 and 33.

An attempt was made to eliminate the possibility of the oxazolidine formation by using 2-methoxyethylamine. Again an alternate cyclization product 37 was isolated.

Although not containing the potential for covalent bonding, 25 was tested for cardiovascular activity. At doses as high as 200 mg/kg, 25 showed no significant cardiovascular activity.


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