8-(1-heptanoylethene-1-yl)-13-methylcoptisine chloride

• 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: 8-(1-heptanoylethene-1-yl)-13-methylcoptisine chloride
• 英文别名: 2-(24-Methyl-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-octaen-14-yl)non-1-en-3-one;chloride；2-(24-methyl-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-octaen-14-yl)non-1-en-3-one;chloride
• 化学式: C₂₉H₃₀NO₅*Cl
• 分子量: 508.014
• InChiKey: ZRZCVBZHRBLBCM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氯化黄连碱 、 仲辛酮 在 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 8-(1-heptanoylethene-1-yl)-13-methylcoptisine chloride
  参考文献：
  名称：

  Derivatives Of Protoberberine Biological Alkaloids And Use Of Same Inhibiting Ulcerative Colitis

  摘要：

  本文披露了通过对原生物碱类季铵盐的源材料进行衍生反应而产生的原生物碱类季铵盐的衍生物或其生理上可接受的盐，以及其制备方法和药用用途。原生物碱类季铵盐的衍生物或其生理上可接受的盐显示出抑制溃疡性结肠炎的活性，并可用于制备相应药物。

  公开号：

  US20150031717A1

文献信息

• Derivatives Of Protoberberine Biological Alkaloids And Use Of Same Inhibiting Ulcerative Colitis
  申请人：Institute of Materia Medica, Chinese Academy of Medical Sciences

  公开号：US20150031717A1

  公开（公告）日：2015-01-29

  Disclosed are derivatives of protoberberine biological alkaloids or physiologically acceptable salts thereof produced by means of a derivative reaction of a source material of biological alkaline quaternary ammonium salts of protoberberine alkaloids, a preparation method for same and pharmaceutical uses thereof. The derivatives of protoberberine biological alkaloids or the physiologically acceptable salts thereof show activity inhibiting ulcerative colitis and can be used in the preparation of drugs for same.

  本文披露了通过对原生物碱类季铵盐的源材料进行衍生反应而产生的原生物碱类季铵盐的衍生物或其生理上可接受的盐，以及其制备方法和药用用途。原生物碱类季铵盐的衍生物或其生理上可接受的盐显示出抑制溃疡性结肠炎的活性，并可用于制备相应药物。
• DERIVATIVES OF PROTOBERBERINE BIOLOGICAL ALKALOIDS AND USE OF SAME INHIBITING ULCERATIVE COLITIS
  申请人：Institute of Mataria Medica, Chinese Academy of Medical Sciences

  公开号：EP2789612B1

  公开（公告）日：2018-08-15
• Synthesis of quaternary 8-(1-acylethene-1-yl)-13-methylcoptisine chlorides and their selective growth inhibitory activity between human cancer cell lines and normal intestinal epithelial cell-6
  作者：Zhi-Hui Zhang、Yu Yan、An-Jun Deng、Hai-Jing Zhang、Zhi-Hong Li、Tian-Yi Yuan、Lian-Hua Fang、Lian-Qiu Wu、Guan-Hua Du、Hai-Lin Qin

  DOI：10.1016/j.cclet.2017.08.026

  日期：2018.1

  In this paper, quaternary 8-(1-acylethene-1-yl)-13-methylcoptisine chlorides targeting thioredoxin reductases (TrxRs) were designed to test the growth inhibitory activity against human cancer cell lines and the effect on viability of the normal intestinal epithelial cell-6 (IEC-6) in vitro and to evaluate structure-activity relationship (SAR). The introduced alpha, beta-unsaturated ketone groups at C-8 consisting of n-alkanoyls possessing five to ten carbons or aroyls or cyclohexylcarbonyl increased the tested activity against the target cancer cell lines. By and large, this type of improvement was increasingly graced by the elongation of the aliphatic chain of the n-alkanoyls in the range of less than ten carbon atoms. The relatively more polar 1-acylethene-1-yls displayed no effect on improving the activity. All the explored aroyls showed significant effect on improving the activity of the target compounds against the tested cancer cell lines with no SAR being observed. The findings of this study suggested that oil/water partition coefficient of the test compounds was one of the key factors impacting the target activity against the tested cancer cell lines. At the concentration of 10 mu mol/L, except for the compounds with n-alkanoyls possessing seven or more carbons or with alpha-naphthoyl, none of the other compounds displayed obvious cytotoxicity on normal IEC-6 cell when co-incubated. The survival rate of IEC-6 cell ranged from 75% to 100% for the noncytotoxic compounds. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.