(1R,2S,10R,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-hexaen-12-one | 880262-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (1R,2S,10R,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-hexaen-12-one
• CAS: 880262-77-1
• 化学式: C₂₅H₃₁N₃O₅
• 分子量: 453.538
• InChiKey: JSTWPSLKUURUMN-GSRZOBFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2S,10R,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-hexaen-12-one 在 lithium aluminium tetrahydride 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 23.5h， 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：

  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：

  L-3,4-二羟基苯基丙氨酸甲酯盐酸 在 盐酸 、 lithium aluminium tetrahydride 、 甲酸 、 草酰氯 、 氢溴酸 、 sodium acetate 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 乙酸酐 、 potassium carbonate 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 40.5h， 生成 (1R,2S,10R,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-hexaen-12-one
  参考文献：
  名称：

  Synthesis and antitumor activity of simplified ecteinascidin–saframycin analogs

  摘要：

  Two series of simplified analogs of the ecteinascidin-saframycin type alkaloids were prepared from L-DOPA. Their in vitro antitumor activity was tested against three human cancer cell lines (HCT-8 colon carcinoma, Bel-7402 liver carcinoma, and BGC-823 gastric carcinoma). Among these compounds, the ester analogs have stronger activities than those of amide analogs in general. Among them, 1-naphthalene carboxylate ester analog 31 has the strongest activity against BGC-823 cells. F (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.069

文献信息

• 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.
• Synthesis and antitumor activity of simplified ecteinascidin–saframycin analogs
  作者：Zhan-Zhu Liu、Ye Wang、Ye-Feng Tang、Shi-Zhi Chen、Xiao-Guang Chen、Hong-Yan Li

  DOI：10.1016/j.bmcl.2005.11.069

  日期：2006.3

  Two series of simplified analogs of the ecteinascidin-saframycin type alkaloids were prepared from L-DOPA. Their in vitro antitumor activity was tested against three human cancer cell lines (HCT-8 colon carcinoma, Bel-7402 liver carcinoma, and BGC-823 gastric carcinoma). Among these compounds, the ester analogs have stronger activities than those of amide analogs in general. Among them, 1-naphthalene carboxylate ester analog 31 has the strongest activity against BGC-823 cells. F (C) 2005 Elsevier Ltd. All rights reserved.