Journal of Interdisciplinary Undergraduate Research


Cardiovascular disease defines disorders of the heart and blood vessels, and is the number one cause of death in America. Diltiazem and clentiazem are common calcium channel blockers incorporated into drugs used to treat various cardiovascular diseases. Methods to synthesize 5-[2-(dimethylamino)ethyl]-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one, an analog of the core of diltiazem and clentiazem, using cost-efficient starting materials allows for affordable treatment and increased availability to affected individuals. N-(N,N-dimethylethanamine)-4-aminophenol can be oxidized to form a quineoneimine, which can be further reacted with 3-mercaptopropionic acid via Michael addition. Subsequent addition of a coupling reagent, N,N'-dicyclocarbodiimide (DCC),1 produces 5-[2-(dimethylamino)ethyl]-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one, analogous to the core structure of diltiazem and clentiazem. Final compounds can then be subjected to biological testing to determine successful inhibition of calcium channels leading to vasodilation. This four step total synthesis approach provides an innovative synthesis methodology.