(6S,7R,9R,15R)‐9‐(aminomethyl)‐2,3,11,12‐tetramethoxy‐16‐methyl‐6,7,9,14,14a,15‐hexahydro‐5H‐6,15‐ep‐iminobenzo[4,5]azocino[1,2‐b]isoquinoline‐7‐carbonitrile | 1430398-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6S,7R,9R,15R)‐9‐(aminomethyl)‐2,3,11,12‐tetramethoxy‐16‐methyl‐6,7,9,14,14a,15‐hexahydro‐5H‐6,15‐ep‐iminobenzo[4,5]azocino[1,2‐b]isoquinoline‐7‐carbonitrile
• 英文别名: (1R,2S,10R,12R,13S)-10-(aminomethyl)-6,7,17,18-tetramethoxy-21-methyl-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4,6,8,15,17,19-hexaene-12-carbonitrile
• CAS: 1430398-32-5
• 化学式: C₂₆H₃₂N₄O₄
• 分子量: 464.564
• InChiKey: ZWVFFJAWOIZPEA-SSSYTOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-甲氧基肉桂酸 、 (6S,7R,9R,15R)‐9‐(aminomethyl)‐2,3,11,12‐tetramethoxy‐16‐methyl‐6,7,9,14,14a,15‐hexahydro‐5H‐6,15‐ep‐iminobenzo[4,5]azocino[1,2‐b]isoquinoline‐7‐carbonitrile 在 4-二甲氨基吡啶 、 1,2-二氯乙烷 作用下， 反应 7.0h， 生成
  参考文献：
  名称：

  Synthesis and cytotoxicity of 3-aryl acrylic amide derivatives of the simplified saframycin–ecteinascidin skeleton prepared from l -dopa

  摘要：

  Twenty four compounds with diversified 3-aryl acrylic amide side chains of the simplified saframycin-ecteinascidin pentacyclic skeleton were synthesized via a 14-step stereospecific route starting from L-dopa. The cytotoxicities of these compounds were tested against eight human tumor cell lines including HCT-8, BEL-7402, BGC-803, A549, A2780, MCF-7, MX-1, and MDA-MB-231. Most of these compounds exhibited potent antitumor activity, and a preliminary structure-activity relationship (SAR) was discussed. Compound 28 with 3-thiophenyl acrylic amide side chain exhibited selective cytotoxicity against MDA-MB-231 cell line with the IC50 value of 50 nM. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.033
• 作为产物：
  描述：

  (6S,7R,9R,15R)‐9‐(hydroxymethyl)‐2,3,11,12‐tetramethoxy‐16‐methyl‐6,7,9,14,14a,15‐hexahydro‐5H‐6,15‐ep‐iminobenzo[4,5]azocino[1,2‐b]isoquinoline‐7‐carbonitrile 在 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.5h， 生成 (6S,7R,9R,15R)‐9‐(aminomethyl)‐2,3,11,12‐tetramethoxy‐16‐methyl‐6,7,9,14,14a,15‐hexahydro‐5H‐6,15‐ep‐iminobenzo[4,5]azocino[1,2‐b]isoquinoline‐7‐carbonitrile
  参考文献：
  名称：

  简化的四氢异喹啉类似物的设计、合成和生物学评价

  摘要：

  制备了一系列四氢异喹啉衍生物，并研究了其对几种人癌细胞系的抗肿瘤活性，包括 Ketr3、BEL-7402、BGC-823、KB、HCT-8、MCF-7、HeLa、A2780、A549 和 HT- 1080.化合物20是Phascidin 650的类似物，在体外表现出良好的广谱抗肿瘤活性。然而，C-22位侧链简化的化合物19和21并没有表现出明显的抗肿瘤活性，表明该类化合物的C-22位侧链对其活性影响较大。化合物20和酞菁650体内活性的差异也表明骨架结构上的取代基对体内活性的显着影响。

  DOI：

  10.1002/ardp.202300453

文献信息

• Synthesis and cytotoxicity screening of derivatives of the simplified ecteinascidin pentacyclic skeleton as anticancer agents
  作者：Ju Guo、Yang Yang、Nan Wang、Zhanzhu Liu

  DOI：10.1016/j.tetlet.2018.07.027

  日期：2018.8

  A series of new ecteinascidin pentacyclic-derived compounds bearing aryl carboxylic amide side chains at C-22 have been designed and synthesized. The cytotoxicity evaluation confirmed their potent antitumor activity by use of eight different cell lines. Studies on the structure-activity relationship of them showed that the chemical structure of C-22 pendants have great effects on the tumor-killing

  设计并合成了一系列在C-22上带有芳基羧基酰胺侧链的新的十碳胞苷五环衍生物。细胞毒性评估通过使用八种不同的细胞系证实了其有效的抗肿瘤活性。对它们的构效关系的研究表明，C-22侧基的化学结构对杀肿瘤活性有很大的影响。值得注意的是，化合物6，7和8与苯并[ b ]噻吩-2-甲酰胺吊坠表现出优异的广谱的抗肿瘤活性与低IC 50个的10个值-7  M.
• Synthesis and cytotoxicity of 3-aryl acrylic amide derivatives of the simplified saframycin–ecteinascidin skeleton prepared from l -dopa
  作者：Ju Guo、Wenfang Dong、Wei Liu、Zheng Yan、Nan Wang、Zhanzhu Liu

  DOI：10.1016/j.ejmech.2013.01.033

  日期：2013.4

  Twenty four compounds with diversified 3-aryl acrylic amide side chains of the simplified saframycin-ecteinascidin pentacyclic skeleton were synthesized via a 14-step stereospecific route starting from L-dopa. The cytotoxicities of these compounds were tested against eight human tumor cell lines including HCT-8, BEL-7402, BGC-803, A549, A2780, MCF-7, MX-1, and MDA-MB-231. Most of these compounds exhibited potent antitumor activity, and a preliminary structure-activity relationship (SAR) was discussed. Compound 28 with 3-thiophenyl acrylic amide side chain exhibited selective cytotoxicity against MDA-MB-231 cell line with the IC50 value of 50 nM. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, and biological evaluation of simplified tetrahydroisoquinoline analogs
  作者：Yang Yang、Yi Gao、Siyu Chen、Ju Guo、Yanggen Hu

  DOI：10.1002/ardp.202300453

  日期：2023.12

  were prepared and their antitumor activity was studied against several human carcinoma cell lines, including Ketr3, BEL-7402, BGC-823, KB, HCT-8, MCF-7, HeLa, A2780, A549, and HT-1080. Compound 20, an analog of phthalascidin 650, exhibited good broad-spectrum antitumor activity in vitro. However, compounds 19 and 21, in which the side chains at C-22 are simplified, showed no obvious antitumor activity

  制备了一系列四氢异喹啉衍生物，并研究了其对几种人癌细胞系的抗肿瘤活性，包括 Ketr3、BEL-7402、BGC-823、KB、HCT-8、MCF-7、HeLa、A2780、A549 和 HT- 1080.化合物20是Phascidin 650的类似物，在体外表现出良好的广谱抗肿瘤活性。然而，C-22位侧链简化的化合物19和21并没有表现出明显的抗肿瘤活性，表明该类化合物的C-22位侧链对其活性影响较大。化合物20和酞菁650体内活性的差异也表明骨架结构上的取代基对体内活性的显着影响。