Journal of Integrative Natural Science (통합자연과학논문집)

The Basic Science Institute Chosun University (조선대학교 기초과학연구원)
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Crystal Structure Analysis of 6-Ethoxy-3-phenyl-5a,9a-dihydro-3H-chromen[4,3-c][1,2]oxazole-3a(4H)-carbonitrile

  • Malathy, P. (CAS in Crystallography and Biophysics, University of Madras) ;
  • Sharmila, P. (Department of Physics, Presidency College) ;
  • Srinivasan, J. (Department of Organic Chemistry, University of Madras) ;
  • Manickam, Bakthadoss (Department of Organic Chemistry, University of Madras) ;
  • Aravindhan, S. (Department of Physics, Presidency College)
  • Received : 2016.05.02
  • Accepted : 2016.06.25
  • Published : 2016.06.30
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Abstract

The crystal structure of the potential active 6-ethoxy-3-phenyl-5a,9a-dihydro-3H-chromen[4,3-c][1,2]oxazole-3a(4H)-carbonitrile ($C_{19}H_{15}N_2O_3$) has been determined from single crystal X-ray diffraction technique. The title compound crystallizes in the monoclinic space group C2/c with unit cell dimension a= 29.3026(9) ${\AA}$, b= 6.7695(2) ${\AA}$ and c= 19.7597(6) ${\AA}$ [${\alpha}= 90^{\circ}$, ${\beta}= 125.709(10)^{\circ}$ and ${\gamma}= 90^{\circ}$]. Single crystals suitable for X-ray diffraction were obtained by slow evaporation method, the isoxazole and six membered pyran rings adopts envelope conformation. The crystal packing of the molecules is stabilized by the weak $C-H{\ldots}N$ 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. E63, pp. o1437-o1438, 2007.
  5. M. Gabor and F. Kallay, "The pharmacology of benzopyrone derivatives and related compounds", Akademiai Kiado, 1986.
  6. S. X. Cai, "Small molecule vascular disrupting agents: potential new drugs for cancer treatment", Recent Pat. Anti-Canc., Vol. 2, pp. 79-101, 2007. https://doi.org/10.2174/157489207779561462
  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. A64, pp. 112-122, 2008.
  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. P. Malathy, G. Jagadeesan, J. Srinivasan , and M. Bakthadoss, ''Crystal structure analysis of 3-(4-ethylphenyl)- 3Hchromeno[4,3-c]isoxazole-3a(4H)-carbonitrile'', J. Chosun Natural Sci., Vol. 8, pp. 250-257, 2015. https://doi.org/10.13160/ricns.2015.8.4.250
  20. G. Jagadeesan, J. Srinivasan, and M. Bakthadoss "Crystal structure analysis of methyl-3-phenyl-3H-chromeno[ 4,3-c]isoxazole-3a(4H)carboxylate", J. Chosun Natural Sci., Vol. 8, pp. 184-191, 2015. https://doi.org/10.13160/ricns.2015.8.3.184
  21. D. Cremer and J. A. Pople, "General definition of ring puckering coordinates". J. Am. Chem. Soc., Vol. 97, pp. 1354-1358, 1975. https://doi.org/10.1021/ja00839a011