Abstract
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.
Graphical Abstract
Single crystal X-ray diffraction studies revealed that conversion of 1-tert-butyl-3-hydroxymethyl-3-nitroazetidine to 1-bromoacetyl-3,3-dinitroazetidine results inflattening of the azetidine ring due to sp2 hybridization of the ring nitrogen, and a crystal density increase of 0.725 Mg/m3 (1.232 vs. 1.957 Mg/m3 respectively) is observed.
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References
Hiskey MA, Stinecipher MM, Brown JE (1993) J Energ Mater 11:157–166
Hiskey MA, Johnson MC, Chavez DE (1999) J Energ Mater 17:233–254
Archibald TG, Gilardi R, Baum K, George C (1990) J Org Chem 55:2920–2924
Axenrod T, Watnick C, Yazdekhasti H, Dave PR (1995) J Org Chem 60:1959–1964
Marchand AP, Rajagopal D, Bott SG (1995) J Org Chem 60:4943–4946
Katritzky AR, Cundy DJ, Chen J (1994) J Heterocycl Chem 31:271–275
Bednarski MD, Oehler LM, Knox S, Cannizzo L, Warner K, Wardle R, Velarde S, Ning S (March 24, 2009) U.S. Patent US7,507,842 B2
Ning S, Bednarski M, Oronsky B, Scicinski J, Saul G, Knox SJ (2012) Cancer Res 72:2600–2608
Straessler NA, Lesley MW, Cannizzo LF (2012) Org Process Res Dev 16:512–517
Kornblum N, Singh HK, Kelly WJ (1983) J Org Chem 48:332–337
Garver LC, Grakauskas V, Baum K (1985) J Org Chem 50:1699–1702
Allen FH (2002) Acta Cryst B58:380–388
Hiskey MA, Coburn MD, Mitchell MA, Benicewicz BC (1992) J Heterocycl Chem 29:1855–1856
Acknowledgments
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).
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Deschamps, J.R., Cannizzo, L.F. & Straessler, N.A. Structure of 1-tert-Butyl-3-hydroxymethyl-3-nitroazetidine and 1-Bromoacetyl-3,3-dinitroazetidine, an Investigative Anticancer Agent Derived from Energetic Materials. J Chem Crystallogr 43, 306–309 (2013). https://doi.org/10.1007/s10870-013-0421-2
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DOI: https://doi.org/10.1007/s10870-013-0421-2