DOI QR코드

DOI QR Code

The Crystal Structure of One Natural Compound Cyclo-(1,10-Docandiamino-11,20-Docanedioic) Amide (1,12-Diazacyclodocosane-2,11-Dione)


Abstract

1,12-diazacyclodocosane-2,11-dione was first isolated from a plant Phyllanthus niruri Linn. Its structure has been determined by means of spectroscopy methods and X-ray crystallography. Two peptide groups in the big ring (lactam) are the main factors influencing intermolecular contacts. The hydrogen-bond interaction of these hydrophilic groups is observed in the crystal structure. Meanwhile, C-H···O hydrogen bonds in molecules contribute to the formation of the whole crystal. These two kinds of hydrogen-bond form six- member rings among molecules. This compound crystallizes in the triclinic space group P-1 with a= 9.588(1) $\AA$, b= $9.850(1)\AA$, c = $11.810(1)\AA$, $\alpha=$ 68.18(1)$^{\circ}C$ , $\beta=$ 84.98(1), $\gamma$ = 86.03(1)$^{\circ}C$ , V = $1030.66(17)\AA3$ , Z = 2. A disorder of five-member carbon chain in the whole ring is observed in the title compound. The bond angle 105.8(4) is determined for a extreme configuration C(14)-C(15)-C(16), and 117.7(10) for another extreme configuration C(14')-C(15')-C(16'). In this crystal, two molecules are tied each other by short intermolecular hydrogen bonds, the oxygen atom being tied by hydrogen bond to nitrogen atom of another two molecules. The NMR and IR spectral data coincides to the structure of the compound.

Keywords

References

  1. Thyagarajan, S. P. et al. The Lancet. 1988, 1, 764.
  2. Wan, L.; Jiang, Z.-Z.; Huang, B. Z. Xinzhongyi. 1997, 29(5), 39 (China).
  3. Ogata, T.; Higuchi, H. et al. AIDS Res. Hum. Retroviruses. 1992, 8(11), 1937. https://doi.org/10.1089/aid.1992.8.1937
  4. Calixto, J. B.; Santos, R. S. A.; Paulino, N. Cient. Cult. 1997, 49(5/6), 422.
  5. Joy, K. L.; Kuttan, R. J. Clin. Biochem. Nutr. 1998, 24(3), 133. https://doi.org/10.3164/jcbn.24.133
  6. Ott, M.; Thyagarajan, S. P.; Gupta, S. Eur. J. Clin. Invest. 1997, 27(1), 908. https://doi.org/10.1046/j.1365-2362.1997.2020749.x
  7. Lee, C. D.; Ott, M.; Thyagarajan, S. P. Eur. J. Clin. Invst. 1996, 26(12), 1069. https://doi.org/10.1046/j.1365-2362.1996.410595.x
  8. Syamasundar, K. V.; Bikram Singh; Thakur, R. S. J. Ethropharmacol. 1985, 14(1), 41. https://doi.org/10.1016/0378-8741(85)90026-1
  9. Hussaain, R. A.; Dickey, J.K.; Rosser, M. P. J. Nat. Prod. 1995, 58(10), 1515. https://doi.org/10.1021/np50124a006
  10. Polya, G. M.; Wang, B. H. et al. Phytochemistry 1995, 38(2), 307. https://doi.org/10.1016/0031-9422(94)00547-7
  11. Eur. Pat. Appl. EP.199, 429, 1986.
  12. Rajeshkumar, N. V.; Kuttan, R. Journal of Enthnopharmacology 2000, 73, 215. https://doi.org/10.1016/S0378-8741(00)00311-1
  13. Wei, W. X.; Gong, X. G.; Ishrud, O.; Pan, Y. J. Bull. Korean Chem. Soc. 2002, 23(6), 896. https://doi.org/10.1007/s11814-006-0005-3
  14. Gutman, A. L.; Meyer, E.; Xu, Y.; Abell, C. Tetrahedron Letter 1992, 33(27), 3943. https://doi.org/10.1016/S0040-4039(00)74825-8
  15. Sheldrick, G. M. SHELXTL-Plus, Structure Determination Software Programs, Siemens Analytical X-Ray Instruments; Madison, WI, 1990.
  16. International Tabales for X-ray Crystallography, VOL. IV, Table 2.2A, Kynoch Press: Birmingham, England, 1974.
  17. Suctton, P. W.; Bradley, A.; Mark, R. J.; Elsegood, M. R. J.; Farras, J.; Jackson, R. F. W. Tetrahetron Letters 1999, 40, 2629. https://doi.org/10.1016/S0040-4039(99)00234-8
  18. Wawrzycka, I.; Stepniak, K.; Awomir, M. S.; KozioTadeusz Lis Anna E.; Abboud, K. A. Journal of Molecular Structure 1999, 474, 157. https://doi.org/10.1016/S0022-2860(98)00569-9

Cited by

  1. : An Ethnopharmacological, Phytochemical, and Pharmacological Review vol.2016, pp.1741-4288, 2016, https://doi.org/10.1155/2016/7584952
  2. Two new compounds from Phyllanthus niruri vol.40, pp.5, 2004, https://doi.org/10.1007/s10600-005-0011-4