Sudan Medical Laboratory Journal

Omdurman Islamic University

Tetracycline's, (TCs) are well-known as antibiotics and their antibacterial action is recognized as very dynamic molecules. Emerging new technological advances in research have led to the search for the synthesis of further derivatives of tetracyclines that endow new characteristics and properties that fortify their therapeutic actions. A large number of alkyl derivatives have been synthesized in order to correlate their structure and reactivity with their pharmacological potential. One of the targets of this study is to attempt a chemical synthesis to produce two such derivatives. 

The second aim of this work is to introduce a new framework for the classification of old and new generations of TCs, using a medicinal chemistry approach to the structure of those drugs

The Mannich base reaction was adopted for the synthesis of two tautomeric forms of amino-N-(lysinomethyl)-tetracycline. The reaction included a three-component-single-pot reaction in which a secondary amine reacts with an aldehyde, tetrahydrofuran and an active hydrogen compound. The attempt was successfully carried out and yielded the two isomers. The confirmatory tests were carried out employing the NMR Spectroscopy detection technique.

The main aim of this study is to prepare two isomers of amino-N-(lysinomethyl)-tetracycline as a  new antibiotic. The study also makes attempts for a drug discovery.

Method: In this study Mannich base reaction method is followed in order to prepare two isomers of amino-N-(lysinomethyl)-tetracycline. The products were detected by NMR Spectroscopy.

Results:  Synthesis of tetracycline with Mannich side chain gavetwo isomers of amino-N-(lysinomethyl)-tetracycline hydrochloride and the reaction was illustrated by the following equation