Design and synthesis of a benzopentathiepin drug-conjugate

ORGN 687

Adaickapillai Mahendran, agreer@brooklyn.cuny.edu1, David Aebisher1, Angela Vuong1, Yaqiong Gong2, Robert Bittman2, and Alexander Greer1. (1) Department of Chemistry, City University of New York, Brooklyn College, Brooklyn, NY 11210, (2) Department of Chemistry and Biochemistry, City University of New York, Queens College, Flushing, NY 11367
The synthesis of a benzopentathiepin “conjugated” to a ceramide has been accomplished. The polysulfane-ceramide conjugate was synthesized in 9 steps and 1.6% overall yield. The final step of the synthesis involved the reaction of 7-carboxybenzopentathiepin p-nitrophenyl ester with D-erythrosphingosine, which led to the formation of an amide bond. The development of conjugation chemistry of polysulfanes beyond our lead ceramide compound should unveil which conjugate moieties are best suited to polysulfanes to facilitate drug delivery.