N-benzylevodiamine | 1253282-90-4

• 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-benzylevodiamine
• 英文别名: 3-benzyl-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: 1253282-90-4
• 化学式: C₂₆H₂₃N₃O
• 分子量: 393.488
• InChiKey: JLZMNPQHVZPOMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzylevodiamine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以56%的产率得到C₂₆H₂₅N₃O₂
  参考文献：
  名称：

  吴茱萸碱衍生物的开环合成及其生物活性评价

  摘要：

  作为从吴茱萸中提取的主要生物活性成分，吴茱萸碱具有多种药理活性。本文选择吴茱萸碱作为起始原料与不同的卤化物反应。经 TFA 处理后，一系列新型开环吴茱萸碱衍生物3a-o以中等至高产率成功合成。这些获得的化合物在MTT测定的体外试验中表现出对BGC803和SW480的中等至良好的抗肿瘤活性。结果表明，己基取代吴茱萸碱衍生物（3j，R=己基）对BGC803和SW480具有较强的抗肿瘤活性。

  DOI：

  10.1111/cbdd.13996
• 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-benzylevodiamine
  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。
• Synthesis of ring opening of evodiamine derivatives and evaluation on their biological activity
  作者：Weihang Guo、Xianheng Wang、Jidong Zhang、Tingting Zhang、Hongfeng Lv、Changkuo Zhao

  DOI：10.1111/cbdd.13996

  日期：2022.4

  halides. Upon treatment of TFA, a series of novel ring-opening evodiamine derivatives 3a–o were successfully synthesized in a moderate to high yields. These obtained compounds exhibit a moderate to good antitumor activity against BGC803 and SW480 in vitro test by MTT assay. The results showed that hexyl substituted evodiamine derivative (3j, R=hexyl) has a strong antitumor activity against BGC803 and SW480

  作为从吴茱萸中提取的主要生物活性成分，吴茱萸碱具有多种药理活性。本文选择吴茱萸碱作为起始原料与不同的卤化物反应。经 TFA 处理后，一系列新型开环吴茱萸碱衍生物3a-o以中等至高产率成功合成。这些获得的化合物在MTT测定的体外试验中表现出对BGC803和SW480的中等至良好的抗肿瘤活性。结果表明，己基取代吴茱萸碱衍生物（3j，R=己基）对BGC803和SW480具有较强的抗肿瘤活性。
• ANTI-CANCER PHARMACEUTICAL COMPOSITION FOR TARGETING HEAT SHOCK PROTEIN 70, CONTAINING INDOLOQUINAZOLIDINE ALKALOID
  申请人：SEOUL NATIONAL UNIVERSITY R & DB FOUNDATION

  公开号：US20240140949A1

  公开（公告）日：2024-05-02

  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.