Journal of Integrative Natural Science (통합자연과학논문집)

The Basic Science Institute Chosun University (조선대학교 기초과학연구원)
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Crystal Structure Theory and Applications of 14-Ethoxy-4,6,-dimethyl-8.12- dioxa-4.6-diazatetracyclo [8.8.0.02,7.013,18]octadeca-13,15,17-triene-3,5-dione

  • Ganapathy, Jagadeesan (Department of Physics, Presidency College) ;
  • Sivakumar, G. (Department of Organic Chemistry, University of Madras, Guindy Campus) ;
  • Manickam, Bakthadoss (Department of Organic Chemistry, University of Madras, Guindy Campus) ;
  • Sanmargam, Aravindhan (Department of Physics, Presidency College)
  • Received : 2015.01.24
  • Accepted : 2015.03.25
  • Published : 2015.03.30
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Abstract

In view of the growing medicinal importance of chromene and its derivatives, the single crystal X-ray diffraction study was carried out for the potential active 4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-diazatetracyclo [8.8.0.02,7.013,18]octadeca-2(7),13,15,17-tetraene-3,5,11-trione-2-ethoxyphenyl (2E)-but-2-enoate ($C_{18}H_{20}N_2O_5$). In the title compound are two molecules exist in the asymmetric unit. It crystallizes in the monoclinic space group $P2_1/c$ with unit cell dimension a=14.608(3) ${\AA}$, b=12.845(3) and c= 17.781(4) [alpha & gamma=$90^{\circ}$ beta=$91.233(5)^{\circ}$]. Both pyran and pyran ring of the chromene moiety adopts sofa conformation in the molecule A & B. The crystal structure is stabilized by intramolecular C-H...O hydrogen bond interaction.

Keywords

References

  1. 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)", Pest Manag. Sci., Vol. 22, pp. 41-50, 1988. https://doi.org/10.1002/ps.2780220105
  2. 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
  3. 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
  4. C. S. Xiong, 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
  5. 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
  6. G. P. Ellis, "The chemistry of heterocyclic compounds", John Wiley and Sons Inc, New York, 1997.
  7. M. Gabor and F. Kallay, "The pharmacology of benzopyrone derivatives and related compounds", Akademiai Kiado, pp. 91-126, 1986.
  8. A. Hassanabadi, M. H. Mosslemin, M. Anary-Abbasinejad, and M. Ghasemi, "One-pot synthesis of substituted 4H-chromenes by three-component reaction of alkyl isocyanides, dialkyl acetylenedicarboxylates, and N-aryl-3-hydroxynaphthalene-2-carboxamide", Synthetic Commun., Vol. 41, pp. 3714-3719, 2011. https://doi.org/10.1080/00397911.2010.520184
  9. W. Kemnitzera, S. Jianga, Y. Wanga, S. Kasibhatlaa, C. Crogan-Grundya, M. Bubenikb, D. Labrecqueb, R. Denisb, S. Lamotheb, G. Attardob, H. Gourdeaub, B. Tsenga, J. Drewea, 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
  10. 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
  11. M. Kidwai, S. Saxena, M. K. Rahman 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
  12. 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 Crystallogr. E, Vol. 63, pp. o1437-o1438, 2007. https://doi.org/10.1107/S1600536807000335
  13. 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.
  14. 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. USA., Vol. 97, pp. 7124-7129, 2000. https://doi.org/10.1073/pnas.97.13.7124
  15. Bruker, "APEX2 and SAINT-Plus", Bruker AXS Inc., Madison, 2004.
  16. G. M. Sheldrick, "SHELXS-97 and SHELXL-97, Program for Crystal Structure Solution and Refinement", University of Gottingen, Gottingen, Germary, 1997.
  17. G. M. Sheldrick, "A short history of SHELX", Acta Crystallogr. A, Vol. 64, pp. 112-122, 2008. https://doi.org/10.1107/S0108767307043930
  18. 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.
  19. A. L. Spek, "Structure validation in chemical crystallography", Acta Crystallogr. D, Vol. 65, pp. 148-155, 2009. https://doi.org/10.1107/S090744490804362X
  20. 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

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