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Enantioseparation of Racemic Anti-hepatitis New Drug Bicyclol with Crystallization 被引量：2

Enantioseparation of Racemic Anti-hepatitis New Drug Bicyclol with Crystallization
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摘要 The enantioseparation of anti-hepatitis new drug （±）-bicyclol was performed by optically active alkaloid. The alcoholic acid, the hydrolysate of bicyclol was reacted with optically active alkaloid, such as brucine, strychnine, quinidine etc., the diastereoisomeric salts were obtained by fractional recrystallization, then separately decomposed and esterified to obtain the two enantiomers of bicyclol. The pharmacological study showed that the effect of （-）-bicyclol was more potent than racemic bicyclol two times and the potency of （＋）-bicyclol was incative. The enantioseparation of anti-hepatitis new drug （±）-bicyclol was performed by optically active alkaloid. The alcoholic acid, the hydrolysate of bicyclol was reacted with optically active alkaloid, such as brucine, strychnine, quinidine etc., the diastereoisomeric salts were obtained by fractional recrystallization, then separately decomposed and esterified to obtain the two enantiomers of bicyclol. The pharmacological study showed that the effect of （-）-bicyclol was more potent than racemic bicyclol two times and the potency of （＋）-bicyclol was incative.
作者 Wei HU Yan LI Chun Zhen ZHANG
机构地区 Institute of Materia Medica
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2005年第11期1471-1473,共3页 中国化学快报（英文版）
关键词 （±）-Bicyclol 4 4＇-dimethoxy-2 3 2 3＇-bis（methylenedioxy）-6-hydroxymethyl-6＇-methoxy-carbonyl biphenyl anti-hepatitis resolution. （±）-Bicyclol, 4, 4＇-dimethoxy-2, 3, 2＇, 3＇-bis（methylenedioxy）-6-hydroxymethyl-6＇-methoxy-carbonyl biphenyl, anti-hepatitis, resolution.
分类号 TQ465 [化学工程—制药化工]
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参考文献4

  • 1The test report of the X-ray analysis of single-crystal of bicyclol was deposited in the National Research Center for Analysis of Drugs and Metabolites.
  • 2Y. Q. Liu, X. Q. Han, et al., Chin. J. of Chem., 2002, 20(7), 663.
  • 3Y. Q. Liu, W. J. Lao, et al., Chromatographia, 2000, 52(314), 190.
  • 4H. M. Ho, L. Soo, H. S. Cheol, et al., Enantiomer, 2001, 5(5), 313.

同被引文献12

  • 1Hung HY, Ohkoshi E, Goto M,et al. Antitumor agents. 293. Non-toxic dimethyl-4, 4'-dimethoxy-5, 6, 5', 6'-dimethylenedioxybi- phenyl-2, 2'-dicarboxylate ( DDB ) analogues chemosensitize multidrug-resistant cancer cells to clinical anticaneer drugs[ J]. J Med Chem,2012, 55(11) :5 413 -5 424.
  • 2Sun H, Liu GT. Chemopreventive effect of bicyclol on malignant transformation of WB-F344 rat liver epithelial cells and its effect on related signal transduction in vitro[ J]. Cancer Lett,2006, 236 (2) :239 -249.
  • 3Jin J, Sun H, Wei H, et al. The anti-hepatitis drug DDB chemo- sensitizes mnhidrug resistant cancer cells in vitro and in vivo by inhibiting P-gp and enhancing apoptosis [ J ]. Invest New Drugs, 2007, 25(2) :95 - 105.
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  • 7Ling Y, Ye XL, Zhang ZZ, et al. Novel nitric oxide-releasing derivatives of farnesylthiosalicylic acid : synthesis and evaluation of antihepatocellular carcinoma activity [ ] ]. J Med Chem, 2011, 54(9) :3 251 -3 259.
  • 8Huang ZJ, Zhang YH, Zhao L, et al. Synthesis and anti-human hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid [ J ]. Org Biomol Chem, 2010, 8(3) :632 -639.
  • 9Chen L, Zhang Y, Kong X, et al. Design, synthesis, and antihepa- tocellular carcinoma activity of nitric oxide releasing derivatives of oleanolic acid [J ]. J Med Chem,2008, 51 ( 15 ) :4 834 - 4 838.
  • 10Fu J ,Liu L,Huang Z ,et al. Hybrid molecule from 02-(2,4-dini- trophenyl) diazeniumdiolate and oleanolic acid:a glutathione S- transferase pi-activated nitric oxide prodrug with selective anti- human hepatocellular carcinoma activity and improved stability [ J]. J Med Chem,2013, 56( 11 ) :4 641 -4 655.

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Chinese Chemical Letters
2005年 第11期

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