9'-(2-naphthyl)-noscapine | 1621072-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 9'-(2-naphthyl)-noscapine
• 英文别名: (S)-6,7-dimethoxy-3-((R)-4-methoxy-6-methyl-9-(naphthalen-2-l)-5,6,7,8-etrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one；(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-9-naphthalen-2-yl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
• CAS: 1621072-68-1
• 化学式: C₃₂H₂₉NO₇
• 分子量: 539.585
• InChiKey: UAKMUIIQAAOXBE-SXOMAYOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  诺司卡品 盐酸盐 水合物 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 氢溴酸 、 溴 、 caesium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 9'-(2-naphthyl)-noscapine
  参考文献：
  名称：

  一种那可汀衍生物及其制备方法和应用

  摘要：

  本发明涉及一类具有式Ⅰ结构通式的那可汀(Noscapine)衍生物及其制备方法和应用，其中衍生物中的R取代基为芳基、杂环基团、烷基、烷基羧酸或烷基酰胺。通过对那可汀母环结构进行化学修饰、引入官能团以增强其抗癌活性而获得活性高、副作用低的抗癌药物。

  公开号：

  CN105801588B

文献信息

• Novel 9′-substituted-noscapines: Synthesis with Suzuki cross-coupling, structure elucidation and biological evaluation
  作者：Elena Porcù、Attila Sipos、Giuseppe Basso、Ernest Hamel、Ruoli Bai、Verena Stempfer、Antal Udvardy、Attila Cs. Bényei、Helmut Schmidhammer、Sándor Antus、Giampietro Viola

  DOI：10.1016/j.ejmech.2014.07.050

  日期：2014.9

  Tubulin is a major molecular target for anticancer drugs. The dynamic process of microtubule assembly and disassembly can be blocked by various agents that bind to distinct sites on tubulin, usually its β-subunit. Among the antimitotic agents that perturb microtubule dynamics, noscapinoids represent an emerging class of agents. In particular, 9'-bromonoscapine (EM011) has been identified as a potent noscapine analog. Here we present high yielding, efficient synthetic methods based on Suzuki coupling of 9'-alkyl and 9'-arylnoscapines and an evaluation of their antiproliferative properties. Our results showed that 9'-alkyl and 9'-aryl derivatives inhibit proliferation of human cancer cells. The most active compounds were the 9'-methyl and the 9'-phenyl derivatives, which showed similar cytotoxic potency in comparison to the 9'-brominated derivative. Interestingly these newly synthesized derivatives did not induce cell death in normal human lymphocytes, suggesting that the compounds may be selective against cancer cells. All of these derivatives, except 9'-(2-methoxyphenyl)-noscapine, efficiently induced a cell cycle arrest in the G2/M phase of the cell cycle in HeLa and Jurkat cells. Furthermore, we showed that the most active compounds in HeLa cells induced apoptosis following the mitochondrial pathway with the activation of both caspase-9 and caspase-3. In addition, these compounds significantly reduced the expression of the anti-apoptotic proteins Mcl-1 and Bcl-2.
• 一种那可汀衍生物及其制备方法和应用
  申请人：长沙凯得尔森生物技术有限公司

  公开号：CN105801588B

  公开（公告）日：2018-09-18

  本发明涉及一类具有式Ⅰ结构通式的那可汀(Noscapine)衍生物及其制备方法和应用，其中衍生物中的R取代基为芳基、杂环基团、烷基、烷基羧酸或烷基酰胺。通过对那可汀母环结构进行化学修饰、引入官能团以增强其抗癌活性而获得活性高、副作用低的抗癌药物。