Abstract
Crystal structure of two brom containing aza-tetracyclic fused N-heterocycles including isoxazolidine ring compounds have been determined in single-crystal X-ray diffraction studies. The compound, C14H19BrN2O3, (1), and C12H15BrN2O3, (2), were obtained from a stereospecific[3+2] 1,3-cycloaddition of oxime based tandem nitrone generation reactions. The envelope conformation of the isoxazolidine rings are different, leading the substituents to be pseudoaxial in (1) and pseudoequatorial in (2). The stereochemistry of these fused compounds are exo- and endo-stereoisomer geometry contributed by exo and endo transition state of nitrone 1,3-dipolar cycloaddition reactions. The title compound (1) crystallizes in the monoclinic space group P2 1/n with a = 12.6221(5)Å, b = 7.5917(4) Å, c = 16.2350(9) Å, β = 112.254(5)°, V = 1439.81(12) Å3, and D calc = 1.583 Mg/m3 for Z = 4 and compound (2) crystallizes in the monoclinic space group P2 1/c with a = 11.6906(9) Å, b = 6.4255(7) Å, c = 17.2070(10) Å, β = 109.264(5)°, V = 1220.2(2) Å3, and D calc = 1.716 Mg/m3 for Z = 4. The antibacterial activity of both compounds were investigated for three Gram (+) and two Gram (−) bacteria by employing broth microdilution method and subsequently inhibitory activity against yeast-like fungi was also determined.
Similar content being viewed by others
References
Gothelf, K.V.; Jorgensen, K.A. Chem. Rev. 1998, 863–909; Gothelf, K.V.; Jorgensen, K.A. Chem. Commun. 2000, 1449-1458.
Breuer, E.; Aurich, H.G.; Nielsen, A. Nitrones, Nitronates and Nitroxides; Wiley: New York, 1989; p. 141.
Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; ed. Wiley: New York, 1984; Vol. 2, p. 83; Torssell, K.B.G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH:Weinheim, Germany, 1988.
Iwasa, S.; Tsushima, S.; Shimada, T.; Nishiyama, H. Tetrahedron Lett. 2001, 42, 6715–6717.
Frank, E.; Wölfling, J.; Aukszi, B.; König, V.; Schneider, T.R.; Schneider, G. Tetrahedron 2002, 58, 6843–6849; Kanemasa, S.; Tsuruoka, T.; Yamamoto, H. Tetrahedron Lett. 1995, 36, 5019-5022; Kanemasa, S.; Tsuruoka, T. Chem. Lett. 1995, 49-50; Kanemasa, S.; Tsuruoka, T. Letters 1997, 38, 7777-7780.
Dondas, H.A.; Grigg, R.; Hadjisoteriou, M.; Markandu, J.; Thomas, W.A.; Kennewell, P. Tetrahedron 2000, 56, 10087–10096; Dondas, H.A.; Grigg, R.; Hadjisoteriou, M.; Markandu, J.; Kennewell, P.; Thornton-Pett, M. Tetrahedron 2001, 57, 1119-1128.
Dondas, H.A.; Grigg, R.; Thibault, S. Tetrahedron 2001, 57, 7035–7045; Dondas, H.A.; Grigg, R.; Frampton, C.S. Tetrahedron Lett. 1997, 38, 5719-5722; Dondas, H.A.; Frederickson, M.; Grigg, R.; Markandu, J.; Thornton-Pett, M. Tetrahedron 1997, 53, 14339-14354.
Dondas, H.A.; Grigg, R.; Markandu, J.; Perrior, T.; Suziki, T.; Thibault, S.; Thomas, W.A.; Thornton-Pett, M. Tetrahedron 2002, 58, 161–173; Markandu, J.; Dondas, H.A.; Frederickson, M.; Grigg, R.; Thornton-Pett, M. Tetrahedron 1997, 53, 13165-13176.
Button, G.; Clarke, G.J.; Douglas, J.D.; Eglinton, A.J.; Frydrych, C.H.; Hinks, J.D.; Hird, N.W.; Hunt, E.; Moss, S.F.; Naylor, A.; Nicholson, N.H.; Pearson, M.J. J. Antibiot. (Tokyo) 1996, 49, 1266–1274; Nishi, K.; Imuta, M.; Kimura, Y.; Miwe, H. J. Antibiot. (Tokyo) 1995, 48, 1481-1487; Huang, S.P.; Koyama, Y.; ?Ikeda, D.; Kondo, S.; Takeuchi, T. J. Antibiot. (Tokyo) 1992, 45, 1939-1948.
Hong, C.Y.; Kim, Y.K.; Chang, J.H.; Kim, S.H.; Choi, H.; Nam, D.H.; Kim, Y.Z.; Kwak, J.J. J. Med. Chem. 1997, 40, 3584–3593; Kim, D.J.; Seo, K.J.; Lee, K.S.; Shin, K.J.; Yoo, K.H.; Kim, D.C.; Park, S.W. Bioorg. Med. Chem. 2000, 10, 2799-2802.
National Committee for Clinical Laboratory Standards. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard, M7-A4; Villanova, PA, 1997.
National Committee for Clinical Laboratory Standards. Reference Methods for Broth Dilution Antifungal Susceptibility Testing Yeasts; Approved Standard, M27-A; Villanova, PA, 1997.
Sheldrichk, G.M. Acta Crytallogr., Sect. A 1990, 46, 467–473.
Sheldrichk, G.M. SHELXL 93, Programfor Refinement of Crystal Structures; University of Gottingen: Gottingen, Germany, 1993.
Billodeaux, D.R.; Fronczek, F.R.; Durust, Y. Acta Crystallogr. Sect. C 1999, 55(11), 1943–1945.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Dondas, H.A., Thornton-Pett, M. Crystal structure of two brom containing aza-tetracyclic fused-ring N-heterocycles including isoxazolidine ring. Journal of Chemical Crystallography 34, 459–463 (2004). https://doi.org/10.1023/B:JOCC.0000035387.65738.27
Issue Date:
DOI: https://doi.org/10.1023/B:JOCC.0000035387.65738.27