Mass spectrometry studies of a twenty-four-member library of dithiocarbamate ester analogs of morpholine

CHED 225

Patrick J. Rogers, patrick_rogershu@yahoo.com, Velvet M. Patterson, Minseon Kwak, and Oladapo Bakare, obakare@howard.edu. Department of Chemistry, Howard University, 525 College Street, Washington, DC 20059
In our drug discovery program we found some dithiocarbamate esters to posses interesting biological activities, including anti-cancer activities. To further our studies in this area, we are employing solution phase parallel synthesis to develop libraries of small organic molecules containing the dithiocarbamate functionality. In this study, we report structure elucidation of a small library of dithiocarbamate ester derivatives of morpholine on an Agilent 5973 Inert GCMS. The library of compounds was synthesized by reacting potassium dithiocarbamate salt of morpholine with twenty-four different alkylating agents in a Radley's Carousel Reaction Station. Mass spectral analysis revealed molecular ion for each compound to confirm molecular weight. Fragments at m/z 130 or 86 appeared as base peak for most of the compounds. These two fragment ions included the morpholino- ring system and their mechanism of formation is presented. Further, interpretation of fragmentation leading to other fragment ions that supported our structure characterization is elaborated.