통합자연과학논문집 (Journal of Integrative Natural Science)

조선대학교 기초과학연구원 (The Basic Science Institute Chosun University)
권호 표지
DOI QR코드

DOI QR Code

Crystal and Molecular Structure of 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

  • 투고 : 2013.10.31
  • 심사 : 2013.12.20
  • 발행 : 2013.12.30
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

The crystal structure of 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 ($C_{22}H_{18}N_2O_5$) has been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group $P_12_1/c_1$ with unit cell dimension a=15.2039(8), b=12.3888(6) and c= 9.8162(5) [alpha & $gamma=90^{\circ}$ beta=98.113(2)]. In the structure fused pyrone and pyran rings each adopt a sofa/envelop conformation. The crystal structure is stabilized by intramolecular C-H... O hydrogen bond interaction.

키워드

참고문헌

  1. V. Maddi, S. N. Mamledesai, D. Satyanarayana, and S. Swamy, "Synthesis and antiinflammatory activity of aubstituted (2-oxochromen-3-yl)benzamides", Indian Journal of Pharamceutical Sciences, Vol. 69, pp. 847-849, 2007. https://doi.org/10.4103/0250-474X.39452
  2. S. Kawaii, Y. Tomono, K. Ogawa, M. Sugiura, M. Yano, Y. Yoshizawa, C. Ito, and H. Furukawa, "Antiproliferative effect of isopentenylated coumarins on several cancer cell lines", Anticancer Res., Vol. 21, pp. 1905-1911, 2001.
  3. C. F. Hossain, E. Okuyama, and M. Yamazaki, "A new series of coumarin derivatives having monoamine oxidase inhibitory activity from Monascus anka", Chem. Pharm. Bull., Vol. 44, pp. 1535-1539, 1996. https://doi.org/10.1248/cpb.44.1535
  4. R. K. Goel, R. N. Maiti, M. Manickam, and A. B. Ray, "Antiulcer activity of naturally occurring pyrano- coumarin and isocoumarins and their effect on prostanoid synthesis using human colonic mucosa", Indian J. Exp. Biol., Vol. 35, pp. 1080-1083, 1997.
  5. J. R. Casley-Smith, C. T. Wang, J. R. Casley-Smith, and C. Zi-hai, "Treatment of filarial lymphoedema and elephantiasis with 5,6-benzo-${\alpha}$-pyrone (coumarin)", Br. Med. J., Vol. 307, pp. 1037-1041, 1993. https://doi.org/10.1136/bmj.307.6911.1037
  6. C. R. Su, S. F. Yeh, C. M. Liu, A. G. Damu, T. H. Kuo, P. C. Chiang, K. F. Bastow, K. H. Lee, and T. S. Wu, "Anti-HBV and cytotoxic activities of pyranocoumarin derivatives", Bioorg. Med. Chem., Vol. 17, pp. 6137-6143, 2009. https://doi.org/10.1016/j.bmc.2008.12.007
  7. Z. Q. Xu, K. Pupek, W. J. Suling, L. Enache, and M. T. Flavin, "Pyranocoumarin, a novel anti-TB pharmacophore: synthesis and biological evaluation against Mycobacterium tuberculosis", Bioorg. Med. Chem., Vol. 14, pp. 4610-4626, 2006. https://doi.org/10.1016/j.bmc.2006.02.017
  8. F. Pavao, M. S. Castilho, M. T. Pupo, R. L. A. Dias, A. G. Correa, J. B. Fernandes, M. F. G. F. Da Silva, J. Mafezoli, P. C. Vieir, and G. Oliva, "Structure of Trypanosoma cruzi glycosomal glyceraldehyde-3- phosphate dehydrogenase complexed with chalepin, a natural product inhibitor, at 1.95 A resolution", FEBS Lett., Vol. 520, pp. 13-17, 2002. https://doi.org/10.1016/S0014-5793(02)02700-X
  9. Bruker, APEX2 and SAINT-Plus, Bruker AXS Inc., Madison, 2004.
  10. G. M. Sheldrick, SHELXS-97 and SHELXL-97, Program for Crystal Structure Solution and Refinement, University of Gottingen, Gottingen, 1997.
  11. G. M. Sheldrick. "A short history of SHELX", Acta Cryst. A, Vol. 64, pp. 112-122, 2008. https://doi.org/10.1107/S0108767307043930
  12. L. J. Farrugia. "ORTEP-3 for windows-a version of ORTEP-III with a graphical user interface (GUI)", J. Appl. Crystallog., Vol. 30, p. 565, 1997.
  13. A. L. Spek, "Structure validation in chemical crystallography", Acta Cryst. D, Vol. 65, pp. 48-155, 2009. https://doi.org/10.1107/S010876730802936X
  14. L. J. Farrugia, "WinGX suite for small-molecule single-crystal crystallography", J. Appl. Crystallog., Vol. 32, pp. 837-838, 1999. https://doi.org/10.1107/S0021889899006020
  15. G. Jagadeesan, D. Kannan, M. Bakthadoss, and S. Aravindhan, "14-Ethoxy-4,6,9-trimethyl-8,12-dioxa- 4,6-diazatetracyclo-[8.8.0.02,7.013,18]octadeca-2(7), 13,15,17-tetraene-3,5,11-trione", Acta Cryst. E, Vol. 69, p. o272, 2013. https://doi.org/10.1107/S1600536813000743
  16. G. Jagadeesan, D. Kannan, M. Bakthadoss, and S. Aravindhan, "14-Ethoxy-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", Acta Cryst. E, Vol. 69, p. o80, 2013.
  17. M. Nardelli, "Ring asymmetry parameters from outof- plane atomic displacements", Acta Cryst. C, Vol. 39, pp. 1141-1142, 1983. https://doi.org/10.1107/S0108270183007696

피인용 문헌

  1. Crystal and Molecular Structure of 12-(2-Methoxyphenyl)-9-[(4-methylbenzene)sulfonyl]-22-oxo-13,21-dioxa-9-azapentacyclo [12.8.0.02,11.03,8.015,20]docosa-1(14),3,5,7,15(20),16,18-heptaene-11-carbonitrile vol.7, pp.3, 2014, https://doi.org/10.13160/ricns.2014.7.3.149
  2. Stereoselective construction of functionalized tetracyclic and pentacyclic coumarinopyranpyrazole/pyrimidinedione/coumarin scaffolds using a solid-state melt reaction vol.13, pp.20, 2015, https://doi.org/10.1039/C5OB00442J
  3. Crystal and Molecular Structure of Methyl 12-(3-bromophenyl)-9-[(4-methylbenzene)sulfonyl]-22-oxo-13,21-dioxa-9-azapentacyclo[12.8.0.02,11.03,8.015,20]docosa-1(14),3,5,7,15(20),16,18-heptaene-11-carboxylate vol.7, pp.2, 2014, https://doi.org/10.13160/ricns.2014.7.2.92