coptisine iodide | 6020-84-4

• 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
• 英文名称: coptisine iodide
• 英文别名: Coptisin；6,7-dihydro-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isoquino[3,2-a]isoquinolinylium; iodide；6,7-Dihydro-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isochino[3,2-a]isochinolinylium; Jodid；5,7,17,19-tetraoxa-13-azoniahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(13),2,4(8),9,14,16(20),21,23-octaene;iodide
• CAS: 6020-84-4
• 化学式: C₁₉H₁₄NO₄*I
• 分子量: 447.229
• InChiKey: CPBHUIZDMJHXJO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.8
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  coptisine iodide 在 sodium tetrahydroborate 作用下， 以 乙醚 为溶剂， 生成 4-benzyl-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isoquino[3,2-a]isoquinoline
  参考文献：
  名称：

  Battersby,A.R. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1140 - 1147

  摘要：

  DOI：
• 作为产物：
  描述：

  盐酸小檗碱 在 platinum(IV) oxide 氢气 、 碘 、 sodium acetate 、 三溴化硼 、 溶剂黄146 、 cesium fluoride 作用下， 以 乙醇 、 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 48.0h， 生成 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

文献信息

• 黄连碱卤酸盐的合成方法及其用途
  申请人：西南大学

  公开号：CN104045636B

  公开（公告）日：2016-08-24

  本发明公开了一种黄连碱卤酸盐的合成方法及其用途；黄连碱卤酸盐的合成方法包括以下步骤：1）将甲酸和占甲酸体积0~10%的磷酸作为溶剂，加入无水硫酸铜、氯化钠及乙二醛回流搅拌反应；2）往反应体系中加入N‑(2,3‑亚甲氧基‑N‑苄基)‑β‑(3,4‑亚甲氧基苯基)乙胺，继续回流反应；3）反应完毕后，滤饼水洗去除反应残留物；4）将滤饼放入NaHCO3溶液中加热搅拌，然后趁热过滤，滤液中加入氢卤酸，冷却结晶。本发明将黄连碱卤酸盐的收率从23.4%大幅提高到70.2%以上，大大超出了预料的收率范围，取得了预料不到的技术效果。本发明制备的黄连碱卤酸盐可以用于制备减肥药和防治心血管类疾病药物。
• Alkaloids of Corydalis incisa PERS. III. The Structures of Corydamine Hydrochloride and N-Formyl Corydamine
  作者：GENICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.21.1410

  日期：——

  Two new alkaloids, corydamine hydrochloride, C20H19O4N2Cl, mp235-239° (decomp.) and N-formyl corydamine, C21H18O4N2, mp159.5-160.5°, were isolated from Corydalis incisa PERS. (Papaveraceae) and their structures were established to be II and IX, respectively, by spectroscopic analyses and their chemical conversion to coptisine iodide and anhydrodihydroprotopine-B. Corydamine hydrochloride and N-formyl corydamine are noted as the first naturally occurring alkaloids having the 3-phenyl isoquinoline skeleton.

  从Corydalis incisa PERS.（罂粟科）中分离出了两种新的生物碱，氯化可瑞达明（corydamine hydrochloride），C20H19O4N2Cl，熔点235-239°（分解）和N-甲酰可瑞达明（N-formyl corydamine），C21H18O4N2，熔点159.5-160.5°。通过光谱分析及其与可尔托辛碘化物和无水二氢原花青素-B的化学转化，确定了它们的结构分别为II和IX。氯化可瑞达明和N-甲酰可瑞达明被认为是首批具有3-苯基异喹啉骨架的天然生物碱。
• Battersby,A.R. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1140 - 1147
  作者：Battersby,A.R. et al.

  DOI：——

  日期：——
• Cytotoxicity evaluation of natural coptisine and synthesis of coptisine from berberine
  作者：Maria Laura Colombo、Carlo Bugatti、Andrea Mossa、Nicoletta Pescalli、Laura Piazzoni、Gabriella Pezzoni、Ernesto Menta、Silvano Spinelli、Francis Johnson、Ramesh C Gupta、Lakkaraju Dasaradhi

  DOI：10.1016/s0014-827x(01)01121-1

  日期：2001.7

  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.