Journal of Integrative Natural Science (통합자연과학논문집)

The Basic Science Institute Chosun University (조선대학교 기초과학연구원)
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Crystal Structure Analysis of 3-(4-ethylphenyl)-3H-chromeno[4,3-c]isoxazole-3a(4H)-carbonitrile

  • Malathy, P. (CAS in Crystallography and Biophysics, University of Madras) ;
  • Ganapathy, Jagadeesan (Department of Physics, Presidency College) ;
  • Srinivasan, J. (Department of Organic Chemistry, University of Madras) ;
  • Manickam, Bakthadoss (Department of Organic Chemistry, University of Madras)
  • Received : 2015.10.20
  • Accepted : 2015.12.25
  • Published : 2015.12.30
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Abstract

The crystal structure of the potential active 3-(4-ethylphenyl)-3H-chromeno[4,3-c]isoxazole-3a(4H)-carbonitrile ($C_{19}H_{16}N_2O_2$) has been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group $P2_1/c$ with unit cell dimension a=6.6869 (8) ${\AA}$, b=15.8326 (19) ${\AA}$ and c= 15.237 (2) ${\AA}$ [${\alpha}=90^{\circ}$, ${\beta}=100.663^{\circ}$ and ${\gamma}=90^{\circ}$]. In the structure chromene, isoxazole and carboxylate are almost coplanar each other. All geometrical parameters revelled that chromene ring of pyran ring adopt sofa conformation. The crystal packing is stabilized by intermolecular C-H...N and C-H...O hydrogen bond interaction.

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References

  1. W. Kemnitzer, S. Jiang, Y. Wang, S. Kasibhatla, C. Crogan-Grundy, M. Bubenik, D. Labrecque, R. Denis, S. Lamothe, G. Attardo, H. Gourdeau, B. Tseng, J. Drewe, and S. X. Cai, "Discovery of 4- aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based HTS assay. Part 5: Modifications of the 2- and 3-positions", Bioorg. Med. Chem. Lett., Vol. 18, pp. 603-607, 2008. https://doi.org/10.1016/j.bmcl.2007.11.078
  2. P. Valenti, P. Da Re, A. Rampa, P. Montanari, M. Carrara, and L. Cima, "Benzo-gamma-pyrone analogues of geiparvarin: synthesis and biological evaluation against B16 melanoma cells", Anti-cancer Drug Design, Vol. 8, pp. 349-360, 1993.
  3. G. T. Brooks, A. P. Ottridge, and D. W. Mace, "The effect of some furochromene and benzochromene analogues of 2,2-dimethyl-7-methoxychromene (precocene I) and benzofuran precursors on Oncopeltus fasciatus (dallas) and Locusta migratoria migratorioides (R&F)", J. Pestic. Sci., Vol. 22, pp. 41-50, 1988. https://doi.org/10.1002/ps.2780220105
  4. Q.-G. Tang, W.-Y. Wu, W. He, H.-S. Sun, and C. Guo, "Methyl 2-amino-4-(3-fluoro-phen-yl)-4Hbenzo[ h]chromene-3-carboxyl-ate methanol solvate", Acta Crystallographica Section E: Structure Reports Online, Vol. 63, pp. o1437-o1438, 2007. https://doi.org/10.1107/S1600536807000335
  5. M. Gabor and F. Kallay, "The pharmacology of benzopyrone derivatives and related compounds", Akademiai Kiado, pp. 91-126, 1986.
  6. S. X. Cai, "Small molecule vascular disrupting agents: potential new drugs for cancer treatment", Recent Pat. Anti-cans, Vol. 2, pp. 79-101, 2007.
  7. S. X. Cai, J. Drewe, and S. Kasibhatla, "A chemical genetics approach for the discovery of apoptosis inducers: from phenotypic cell based HTS assay and structure-activity relationship studies, to identification of potential anticancer agents and molecular targets", Curr. Med. Chem., Vol. 13, pp. 2627-2644, 2006. https://doi.org/10.2174/092986706778201521
  8. S. X. Cai, J. Drewe, and W. Kemnitzer, "Discovery of 4-aryl-4H-chromenes as potent apoptosis inducers using a cell- and caspase-based anti-cancer screening apoptosis program (ASAP): SAR studies and the identification of novel vascular disrupting agents", Anti-cancer Agent. Me., Vol. 9, pp. 437- 456, 2009. https://doi.org/10.2174/1871520610909040437
  9. M. Kidwai, S. Saxena, M. K. R. Khan, and S. S. Thukral, "Aqua mediated synthesis of substituted 2- amino-4H-chromenes and in vitro study as antibacterial agents", Bioorg. Med. Chem. Lett., Vol. 15, pp. 4295-4298, 2005. https://doi.org/10.1016/j.bmcl.2005.06.041
  10. J.-L. Wang, D. Liu, Z.-J. Zhang, S. Shan, X. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, and Z. Huang, "Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells", P. Natl. Acad. Sci. U.S.A., Vol. 97, pp. 7124-7129, 2000. https://doi.org/10.1073/pnas.97.13.7124
  11. C. Bruhlmann, F. Ooms, P.-A. Carrupt, B. Testa, M. Catto, F. Leonetti, C. Altomare, and A. Carotti, "Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase", J. Med. Chem., Vol. 44, pp. 3195-3198, 2001. https://doi.org/10.1021/jm010894d
  12. S. R. Kesten, T. G. Heffner, S. J. Johnson, T. A. Pugsley, J. L. Wright, and L. D. Wise, "Design, synthesis, and evaluation of chromen-2-ones as potent and selective human dopamine D4 antagonists", J. Med. Chem., Vol. 42, pp. 3718- 3725, 1999. https://doi.org/10.1021/jm990266k
  13. Bruker, "APEX2 and SAINT-Plus", Bruker AXS Inc., Madison, 2004.
  14. G. M. Sheldrick, "MSHELXS-97 and SHELXL-97, Program for crystal structure solution and refinement", University of Gottingen, Gottingen, Germany, 1997.
  15. G. M. Sheldrick, "A short history of SHELX", Acta Crystallogr. A, Vol. 64, pp. 112-122, 2008. https://doi.org/10.1107/S0108767307043930
  16. L. J. Farrugia, "ORTEP-3 for Windows-A version of ORTEP-III with a graphical user interface (GUI)", J. Appl. Crystallogr., Vol. 30, pp. 565, 1997.
  17. A. L. Spek, "Structure validation in chemical crystallography", Acta Crystallogr. D, Vol. 65, pp. 148- 155, 2009. https://doi.org/10.1107/S090744490804362X
  18. L. J. Farrugia, "WinGX Suite for small-molecule single-crystal crystallography", J. Appl. Crystallogr., Vol. 32, pp. 837-838, 1999. https://doi.org/10.1107/S0021889899006020
  19. G. Jagadeesan, G. Sivakumar, M. Bakthadoss, and S. Aravindhan, "Crystal structure theory and applications of 14-Ethoxy-4,6,-dimethyl-8.12-dioxa-4.6-diazatetracyclo[ $8.8.0.0^{2,7}.0^{13,18}$]octadeca-13,15,17-triene-3,5- dione", J. Chosun Natural Sci., Vol. 8, pp. 19-29, 2015. https://doi.org/10.13160/ricns.2015.8.1.19

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