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Synthesis, Characterization and Crystal Structure of Optically Active L- and D-Histidine Norcantharimide
Corresponding Author(s) : Yanfeng Wang
Asian Journal of Chemistry,
Vol. 26 No. 22 (2014): Vol 26 Issue 22
Abstract
L- and D-histidine norcantharimide was showed significant PP2A inhibitors effect. They were synthesized through a highly efficient combinatorial approach , to a solution of norcantharidin and L-histidine in 95 % EtOH under temperature affords L-histidine norcantharimide in 97 % yield. L-histidine norcantharimide was characterized by X-ray. This single crystal was orthorhombic with the space group P2(1)2(1)2(1). One unit cell dimensions were a = 10.1553(4) Å, b = 10.4840(5) Å and c = 12.8749(6) Å, respectively. a = b = g = 90°, Mr = 305.29, V = 1370.77(11) Å3, D = 1.479 Mg/m3, F(000) = 640 and Z = 4. The crystal structure is stabilized by a network of intermolecular hydrogen bonds involving N-H and COO– group.
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- G.S. Wang, J. Ethnopharmacol., 26, 147 (1989); doi:10.1016/0378-8741(89)90062-7.
- A. McCluskey and J.A. Sakoff, Mini Rev. Med. Chem., 1, 43 (2001); doi:10.2174/1389557013407205.
- A. McCluskey, A.T.R. Sim and J.A. Sakoff, J. Med. Chem., 45, 1151 (2002); doi:10.1021/jm010066k.
- P.A. Eichhorn, M.P. Creyghton and R. Bernards, Biochim. Biophys. Acta Rev. Cancer, 1795, 1 (2009); doi:10.1016/j.bbcan.2008.05.005.
- A. McCluskey, S.P. Ackland, E. Gardiner, C.C. Walkom and J.A. Sakoff, Anticancer Drug Des., 16, 291 (2001).
- A. McCluskey, C. Walkom, M.C. Bowyer, S.P. Ackland, E. Gardiner and J.A. Sakoff, Bioorg. Med. Chem. Lett., 11, 2941 (2001); doi:10.1016/S0960-894X(01)00594-7.
- T.A. Hill, S.G. Stewart, B. Sauer, J. Gilbert, S.P. Ackland, J.A. Sakoff and A. McCluskey, Bioorg. Med. Chem. Lett., 17, 3392 (2007); doi:10.1016/j.bmcl.2007.03.093.
- A. Thaqi, J.L. Scott, J. Gilbert, J.A. Sakoff and A. McCluskey, Eur. J. Med. Chem., 45, 1717 (2010); doi:10.1016/j.ejmech.2010.01.004.
- Y. Zhou, X.J. Zhang, Y.C. Cai, L.J. Xian and Y. Zou, Chin. Pharm. J., 42, 324 (2007).
- Y. Liu and Y.Z. Ling, Chin. J. Pharm., 22, 8 (1991).
- G.M. Sheldrick, SADABS 2.05, University Göttingen, Germany (2002).
- SHELXTL 6.10, Bruker Analytical Instrumentation, Madison, WI, USA, 2000.
- P. Edington and M.M. Harding, Acta Crystallogr., 30, 204 (1974); doi:10.1107/S0567740874002470.
References
G.S. Wang, J. Ethnopharmacol., 26, 147 (1989); doi:10.1016/0378-8741(89)90062-7.
A. McCluskey and J.A. Sakoff, Mini Rev. Med. Chem., 1, 43 (2001); doi:10.2174/1389557013407205.
A. McCluskey, A.T.R. Sim and J.A. Sakoff, J. Med. Chem., 45, 1151 (2002); doi:10.1021/jm010066k.
P.A. Eichhorn, M.P. Creyghton and R. Bernards, Biochim. Biophys. Acta Rev. Cancer, 1795, 1 (2009); doi:10.1016/j.bbcan.2008.05.005.
A. McCluskey, S.P. Ackland, E. Gardiner, C.C. Walkom and J.A. Sakoff, Anticancer Drug Des., 16, 291 (2001).
A. McCluskey, C. Walkom, M.C. Bowyer, S.P. Ackland, E. Gardiner and J.A. Sakoff, Bioorg. Med. Chem. Lett., 11, 2941 (2001); doi:10.1016/S0960-894X(01)00594-7.
T.A. Hill, S.G. Stewart, B. Sauer, J. Gilbert, S.P. Ackland, J.A. Sakoff and A. McCluskey, Bioorg. Med. Chem. Lett., 17, 3392 (2007); doi:10.1016/j.bmcl.2007.03.093.
A. Thaqi, J.L. Scott, J. Gilbert, J.A. Sakoff and A. McCluskey, Eur. J. Med. Chem., 45, 1717 (2010); doi:10.1016/j.ejmech.2010.01.004.
Y. Zhou, X.J. Zhang, Y.C. Cai, L.J. Xian and Y. Zou, Chin. Pharm. J., 42, 324 (2007).
Y. Liu and Y.Z. Ling, Chin. J. Pharm., 22, 8 (1991).
G.M. Sheldrick, SADABS 2.05, University Göttingen, Germany (2002).
SHELXTL 6.10, Bruker Analytical Instrumentation, Madison, WI, USA, 2000.
P. Edington and M.M. Harding, Acta Crystallogr., 30, 204 (1974); doi:10.1107/S0567740874002470.