盐酸人血草碱 | 96087-21-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 中文名称: 盐酸人血草碱
• 英文名称: tetrahydrocoptisine hydrochloride
• 英文别名: (+/-)-stylopine; hydrochloride；(+/-)-Stylopin; Hydrochlorid；tetrahydrocoptisine hydrochloride Coptisine hydrochloride；5,7,17,19-tetraoxa-13-azoniahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-2,4(8),9,15(23),16(20),21-hexaene;chloride
• CAS: 96087-21-7
• 化学式: C₁₉H₁₇NO₄*ClH
• 分子量: 359.809
• InChiKey: WZUQSTMUNWBERD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  40.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 储存条件：
  -20℃

制备方法与用途

化学性质
四氢黄连碱是一种黄色结晶粉末，可溶于甲醇、乙醇和DMSO等有机溶剂。它来源于白屈菜、延胡索块茎以及元胡。

用途
四氢黄连碱具有抗自由基损伤和止痛的作用。

反应信息

• 作为反应物：
  描述：

  盐酸人血草碱 在 碘 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以67%的产率得到coptisine iodide
  参考文献：
  名称：

  Cytotoxicity evaluation of natural coptisine and synthesis of coptisine from berberine

  摘要：

  The crude extract (80% MeOH in water) of Chelidonii herba exhibited very interesting cytotoxicity against brine shrimp (Artemia salina Leach) nauplii and cultured human tumour cell in vitro, the colon carcinoma HT 29 (144 h treatment). Fractionation of the crude extract and bioassay-guided procedures showed that the cytotoxic and,the antitumour activities. were concentrated in the basic extract. On the basis of IR, MS and H-1 NMR the compound responsible of the cytotoxic activity was determined to be coptisine. Cytotoxicity evaluation of-coptisine was next extended to-a panel of human and murine cell lines in comparison with the established antitumour drugs mitoxantrone, doxorubicin (D. x) and cisplatin. (CDDP). Coptisine was cytotoxic on LoVo and HT 29 and less potent on L-1210, and it was partially crossresistant on the human tumour colon cell line resistant to Dx, LoVo/Dx, whereas it was not significantly crossresistant on the murine leukaemia cell line resistant to. CD. DP, L-1210/CDDP. Coptisine alkaloid was then synthesised in gram amount from commercial berberine. A four-step synthetic route was elaborated. The overall yield was about 8-10%. The structural identity of synthetic coptisine was verified by IR and NMR methods. A comparison of the cytotoxic effects on the human tumour colon cell line LoVo and on the murine leukaemia L1210 showed, for both natural and synthetic coptisines, a comparable cytotoxic activity more evident against-HT 29 cell line and LoVo. cell line, while the activity was lower against the L1210 cell line. (C) 2001 Editions scientifiques et medicales. Elsevier SAS.

  DOI：

  10.1016/s0014-827x(01)01121-1
• 作为产物：
  描述：

  盐酸小檗碱 在 platinum(IV) oxide 氢气 、 三溴化硼 、 溶剂黄146 、 cesium fluoride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~95.0 ℃ 、405.3 kPa 条件下， 反应 36.0h， 生成 盐酸人血草碱
  参考文献：
  名称：

  Cytotoxicity evaluation of natural coptisine and synthesis of coptisine from berberine

  摘要：

  The crude extract (80% MeOH in water) of Chelidonii herba exhibited very interesting cytotoxicity against brine shrimp (Artemia salina Leach) nauplii and cultured human tumour cell in vitro, the colon carcinoma HT 29 (144 h treatment). Fractionation of the crude extract and bioassay-guided procedures showed that the cytotoxic and,the antitumour activities. were concentrated in the basic extract. On the basis of IR, MS and H-1 NMR the compound responsible of the cytotoxic activity was determined to be coptisine. Cytotoxicity evaluation of-coptisine was next extended to-a panel of human and murine cell lines in comparison with the established antitumour drugs mitoxantrone, doxorubicin (D. x) and cisplatin. (CDDP). Coptisine was cytotoxic on LoVo and HT 29 and less potent on L-1210, and it was partially crossresistant on the human tumour colon cell line resistant to Dx, LoVo/Dx, whereas it was not significantly crossresistant on the murine leukaemia cell line resistant to. CD. DP, L-1210/CDDP. Coptisine alkaloid was then synthesised in gram amount from commercial berberine. A four-step synthetic route was elaborated. The overall yield was about 8-10%. The structural identity of synthetic coptisine was verified by IR and NMR methods. A comparison of the cytotoxic effects on the human tumour colon cell line LoVo and on the murine leukaemia L1210 showed, for both natural and synthetic coptisines, a comparable cytotoxic activity more evident against-HT 29 cell line and LoVo. cell line, while the activity was lower against the L1210 cell line. (C) 2001 Editions scientifiques et medicales. Elsevier SAS.

  DOI：

  10.1016/s0014-827x(01)01121-1