DOI QR코드

DOI QR Code

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

  • Received : 2014.05.27
  • Accepted : 2014.06.25
  • Published : 2014.06.30

Abstract

The crystal structure of the title compounds with both coumarin and sulfonamide moieties were examined. These two groups have very special for their pharmaceutical and medicinal properties have been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group C2/c with unit cell dimension a = 28.633(3) ${\AA}$, b= 9.3215(7) ${\AA}$ and c= 24.590(2) ${\AA}$ [alpha & gamma=$90^{\circ}$ beta= $115.976(3)^{\circ}$]. In the structure The S1 atom shows a distorted tetrahedral geometry, with O1-S1-O2 [119.74 $(2)^{\circ}$] and N1-S1-C5 [$105.57(1)^{\circ}$] angles deviating from ideal tetrahedral values are attributed to the Thrope-Ingold effect. The sum of bond angles around N1 ($316.2(1)^{\circ}$) indicates that N1 is in sp2 hybridization. The Pyridine ring adopts boat conformation and pyran rings adopt a sofa conformation. The carboxylate group of atoms were disordered over two positions with site occupancy factors 0.598 (9):0.402 (9). Crystal structure and packing is stabilized by $C-H{\ldots}O$ intra and inter molecular hydrogen bond interactions.

Keywords

References

  1. J. Ganapathy, K. Damodharan, B. Manickam, and A. Sanmargam, "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", J. Chosun Natural Sci. Vol. 6, pp. 197-204, 2013. https://doi.org/10.13160/ricns.2013.6.4.197
  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 Å 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. Crystallogr., 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. Crystallogr., Vol. 32, pp. 837-838, 1999. https://doi.org/10.1107/S0021889899006020
  15. A. Bassindale, "The third dimension in organic chemistry", ch. 1, p. 11, New York, John Wiley and Sons, 1984.
  16. 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

Cited by

  1. Molecular Docking Studies of Wolbachia Endosymbiont of Brugia Malayi's Carbonic Anhydrase Using Coumarin-chromene Derivatives Towards Designing Anti-filarial Agents vol.9, pp.4, 2016, https://doi.org/10.13160/ricns.2016.9.4.268