Structure of 1-tert-Butyl-3-hydroxymethyl-3-nitroazetidine and 1-Bromoacetyl-3,3-dinitroazetidine, an Investigative Anticancer Agent Derived from Energetic Materials
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The structures of a novel investigative anticancer agent 1-bromoacetyl-3,3-dinitro azetidine (ABDNAZ, 2) and its synthetic precursor 1-tert-butyl-3-hydroxymethyl-3-nitroazetidine (1) were determined by single crystal X-ray diffraction. The data show that the chemical transformation from 1 to 2 resulted in an increase in crystal density of 0.725 Mg/m3 (1 = 1.232 Mg/m3; 2 = 1.957 Mg/m3). The azetidine ring of 1 is puckered while 2 is planar, consistent with sp2 hybridization of the ring nitrogen following conversion of the tertiary amine to an amide. The structural information will aid in elucidating the biological activity of 2.
Keywords1-Bromoacetyl-3,3-dinitroazetidine ABDNAZ 1-tert-Butyl-3-hydroxymethyl-3-nitroazetidine Anticancer energetic materials Nitrogen-heterocycle
X-ray crystallographic studies were supported in part by the Naval Research Laboratory and the Office of Naval Research. The bioactivity and therapeutic applications of compound 2 are being investigated by RadioRx, Inc. (http://www.radiorx.com, Menlo Park, CA).