N-(4-methoxylbenzyl)evodiamine | 1253282-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-(4-methoxylbenzyl)evodiamine
• 英文别名: 3-[(4-methoxyphenyl)methyl]-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one
• CAS: 1253282-93-7
• 化学式: C₂₇H₂₅N₃O₂
• 分子量: 423.514
• InChiKey: JWSFWJOEOOBNCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,9-二氢-3H-吡啶并(3,4-B)吲哚 在 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N-(4-methoxylbenzyl)evodiamine
  参考文献：
  名称：

  ANTI-CANCER PHARMACEUTICAL COMPOSITION FOR TARGETING HEAT SHOCK PROTEIN 70, CONTAINING INDOLOQUINAZOLIDINE ALKALOID

  摘要：

  The present invention relates to: an anti-cancer pharmaceutical composition for targeting heat shock protein 70, containing an indoloquinazolidine alkaloid; and the like. The indoloquinazolidine alkaloid of the present invention inhibits the growth of tumors and inhibits the expression of HSP70 protein and the colony formation activity of cancer cells, and inhibits the growth of tumors in mouse models with xenografts of a cancer cell line and xenografts of patient-derived cancer, and inhibits the growth of cancer cells resistant to drugs such as pemetrexed, cisplatin, and paclitaxel, and thus is expected to be widely usable in the prevention and treatment of various types of cancer.

  公开号：

  US20240140949A1

文献信息

• Selection of Evodiamine as a Novel Topoisomerase I Inhibitor by Structure-Based Virtual Screening and Hit Optimization of Evodiamine Derivatives as Antitumor Agents
  作者：Guoqiang Dong、Chunquan Sheng、Shengzheng Wang、Zhenyuan Miao、Jianzhong Yao、Wannian Zhang

  DOI：10.1021/jm100387d

  日期：2010.11.11

  target for the development of effective antitumor agents. Structure-based virtual screening was applied to the discovery of structurally diverse TopoI inhibitors. From 23 compounds selected by virtual screening, a total of 14 compounds were found to be TopoI inhibitors. Five hits (compounds 1, 14, 20, 21, and 23) also showed moderate to good in vitro antitumor activity. These novel structures can be considered

  人拓扑异构酶I（TopoI）被认为是开发有效抗肿瘤药物的重要靶标。基于结构的虚拟筛选应用于发现结构多样的TopoI抑制剂。从通过虚拟筛选选择的23种化合物中，总共发现14种化合物是TopoI抑制剂。五次命中（化合物1，14，20，21，和23）也显示中等至体外抗肿瘤活性好。这些新颖的结构可被视为开发新的抗肿瘤先导化合物的良好起点。命中20（evodiamine）被选择用于初步的结构-活性关系研究。将各种基团，包括烷基，苯甲酰基，苄基和酯，引入到戊二胺的吲哚氮原子上。发现取代的苯甲酰基对于抗肿瘤活性和光谱是有利的。4-Cl苯甲酰基衍生物化合物29u是活性最高的化合物，IC 50值在0.049-2.6μM范围内。