Total synthesis of 7-acetamidoquinoline-5, 8-dione-2-carboxylic acid : [an honors thesis (HONRS 499)]
This thesis describes work done as part of an ongoing research project in the synthesis of lavendamycin analogs, including various quinoline-5,8-diones. These smaller compounds form two of the five rings found in the structure of lavendamycin, a potent antibiotic and antitumor drug. The thrust of our research project is to find a compound with high antitumor activity that also has low toxicity and sufficient solubility to make it suitable for clinical applications.The compound described in this thesis is a novel carboxylic acid derived from compounds previously synthesized as part of Dr. Behforouz's research work. Although this acid, due to its poor solubility, would not be suitable for practical applications, it is the hope of our group that this compound may be used as an intermediate in producing other compounds that would selectively enhance solubility and antitumor activity while decreasing cytotoxicity.Due to time constraints none of the acid derivatives (esters and amides) could be prepared and purified prior to this writing. However, work on the project is ongoing by several members within the research group.