(+)-白屈菜碱盐酸盐 | 4312-31-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 苯并菲啶生物碱
• 中文名称: (+)-白屈菜碱盐酸盐
• 中文别名: 白屈菜碱盐酸盐
• 英文名称: [5bR-(5bα,6β,12bα)]-5b,6,7,12b,13,14-hexahydro-13-methyl[1,3]benzodioxo[5,6-c]-1,3-dioxo[4,5-i]phenanthridin-6-ol hydrochloride
• 英文别名: chelidonine hydrochloride；Chelidonine, hydrochloride；(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol;hydrochloride
• CAS: 4312-31-6
• 化学式: C₂₀H₁₉NO₅*ClH
• 分子量: 389.835
• InChiKey: LVURMIFHBFKWNP-PHANBDLMSA-N

物化性质

• 熔点：
  275-283°C
• 溶解度：
  可溶于氯仿、乙醇、甲醇（微溶、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.4
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 (+)-白屈菜碱盐酸盐 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以67.66%的产率得到(1S,12S,13R)-24-methyl-12-prop-2-enoxy-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaene
  参考文献：
  名称：

  Synthesis and biological activity of O-acyl and O-alkyl chelidonine derivatives

  摘要：

  A group of 11 derivatives of chelidonine was obtained by acylations and/or alkylations of the secondary hydroxyl group with the aim of testing their biological activity. This paper focuses on the new derivatives influence on CNS in mice. The highest activity was observed for compounds 2c, 3c and 4, which produced antinociceptive and antiserotoninergic effects, not recorded for the parent alkaloid 1. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01288-0

文献信息

• Quaternary chelidonine and alkaloid derivatives, process for their preparation and their use in the manufacture of medicaments
  申请人：Nowicky, Wassyl, Dipl.-Ing. DDr.

  公开号：EP1459753A1

  公开（公告）日：2004-09-22

  The invention relates to alkaloid reaction products obtainable in a process wherein alkaloids are reacted with an alkylating agent, preferably thiotepa, whereafter unreacted alkylating agent and other water-soluble compounds are removed from the reaction mixture by washing with water or a suitable aqueous solvent, whereafter the reaction mixture is subjected to a treatment with strong acid, preferably hydrogen chloride (HCl), to precipitate a water soluble salt of the reaction products. The precipitated reaction products comprise at least one quaternary alkaloid derivative and are suitable as drugs for prophylactic or therapeutic application, particularly in the treatment of immunological or metabolic dysfunctions, and cancer.

  该发明涉及一种碱性物质反应产物，可通过一种过程获得，在该过程中，碱性物质与烷基化剂发生反应，优选为硫替巴（thiotepa），随后通过用水或适当的水溶性溶剂洗涤来除去未反应的烷基化剂和其他水溶性化合物，然后将反应混合物经过强酸处理，优选为盐酸（HCl），以沉淀反应产物的水溶性盐。沉淀的反应产物包括至少一种季铵碱性物质衍生物，并适用于用于预防或治疗应用的药物，特别是在免疫或代谢功能障碍以及癌症治疗中。
• [EN] QUATERNARY ALKALOID DERIVATIVES OF CHELIDONIUM MAJUS L<br/>[FR] DERIVES ALCALOIDES QUATERNAIRES DE CHELIDONIUM MAJUS L
  申请人：NOWICKY WASSILI

  公开号：WO2006032380A1

  公开（公告）日：2006-03-30

  The invention relates to alkaloid reaction products obtainable in a process wherein alkaloids are reacted with a derivatizing agent, preferably thiotepa or another one of the compounds listed in Fig.3, whereafter unreacted derivatizing agent and other water-soluble compounds are removed from the reaction mixture by washing with water or a suitable aqueous solvent, whereafter the reaction mixture is subjected to a treatment with strong acid, preferably hydrogen chloride (HCI), to precipitate a water soluble salt of the reaction products. The precipitated reaction products comprise at least one quaternary alkaloid derivative and are suitable as drugs for prophylactic or therapeutic application, particularly in the treatment of immunological or metabolic dysfunctions, and cancer.

  本发明涉及一种碱性物质反应产物，该产物可以在一种过程中获得，该过程中碱性物质与衍生化试剂（优选为硫唑磷或图3中列出的其他化合物之一）反应，然后通过用水或适当的水溶性溶剂洗涤来去除未反应的衍生化试剂和其他水溶性化合物，然后将反应混合物用强酸（优选为盐酸）处理，以沉淀反应产物的水溶性盐。沉淀的反应产物包括至少一种季铵碱衍生物，适用于预防或治疗应用的药物，特别是在免疫或代谢功能障碍和癌症的治疗中。
• Production of high purity alkaloids
  申请人：VIPONT PHARMACEUTICAL, INC.

  公开号：EP0379623A1

  公开（公告）日：1990-08-01

  A method for extracting valuable alkaloid mate­rials from plants containing the same comprising slurrying the comminuted plant material in a mixture of water and a cosolvent at a pH of 8.5, adding a nonpolar, water-insoluble, solvent to dissolve the alkaloid, washing the nonpolar phase with acidulated water to convert the alkaloid to the imminium ion or acid salt form, precipitating the alkaloid, and recovering and drying the alkaloid.

  一种从含有有价值生物碱的植物中提取有价值生物碱材料的方法，包括在 pH 值为 8.5 的水和共溶剂混合物中将粉碎的植物材料浆化，加入非极性、不溶于水的溶剂以溶解生物碱，用酸化水洗涤非极性相以将生物碱转化为铵离子或酸性盐形式，沉淀生物碱，以及回收和干燥生物碱。
• Quaternary chelidonine and alkaloid derivatives, process for their preparation and their use in manufacture of medicaments
  申请人：Nowicky Wassyl

  公开号：US20060154947A1

  公开（公告）日：2006-07-13

  The invention relates to alkaloid reaction products obtainable in a process wherein alkaloids are reacted with an alkylating agent, preferably thiotepa, whereafter unreacted alkylating agent and other water-soluble compounds are removed from the reaction mixture by washing with water or a suitable aqueous solvent, whereafter the reaction mixture is subjected to a treatment with strong acid, preferably hydrogen chloride (HCI), to precipitate a water soluble salt of the reaction products. The precipitated reaction products comprise at least one quaternary alkaloid derivative and are suitable as drugs for prophylactic or therapeutic application, particularly in the treatment of immunological or metabolic dysfunctions, and cancer.

  本发明涉及生物碱反应产物，可通过以下工艺获得：生物碱与烷化剂，最好是噻替帕反应，然后用水或适当的水性溶剂洗涤，从反应混合物中除去未反应的烷化剂和其他水溶性化合物，然后用强酸，最好是氯化氢（HCI）处理反应混合物，沉淀反应产物的水溶性盐。析出的反应产物包括至少一种季生物碱衍生物，适合作为预防或治疗药物，特别是用于治疗免疫或代谢功能障碍和癌症。
• QUATERNARY CHELIDONINE AND ALKALOID DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN MANUFACTURE OF MEDICAMENTS
  申请人：Nowicky, Wassyl

  公开号：EP1644012A1

  公开（公告）日：2006-04-12