(2E)-N-{[(6S,7R,9R,14aS,15R)-7-Cyano-6,7,9,14,14a,15-hexahydro-2,3,11,12-tetramethoxy-16-methyl-6,15-imino-5H-isoquino[3,2-b][3]benzazocin-9-yl]methyl}-3-(4-fluorophenyl)-2-propenamide | 1430398-33-6

• 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: (2E)-N-{[(6S,7R,9R,14aS,15R)-7-Cyano-6,7,9,14,14a,15-hexahydro-2,3,11,12-tetramethoxy-16-methyl-6,15-imino-5H-isoquino[3,2-b][3]benzazocin-9-yl]methyl}-3-(4-fluorophenyl)-2-propenamide
• 英文别名: (E)-N-[[(1R,2S,10R,12R,13S)-12-cyano-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-10-yl]methyl]-3-(4-fluorophenyl)prop-2-enamide
• CAS: 1430398-33-6
• 化学式: C₃₅H₃₇FN₄O₅
• 分子量: 612.701
• InChiKey: KIKYRUBPURLADZ-QCIFZFOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 palladium(II) hydroxide 、 溶剂黄146 、 1,2-二氯乙烷 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 32.5h， 生成 (2E)-N-{[(6S,7R,9R,14aS,15R)-7-Cyano-6,7,9,14,14a,15-hexahydro-2,3,11,12-tetramethoxy-16-methyl-6,15-imino-5H-isoquino[3,2-b][3]benzazocin-9-yl]methyl}-3-(4-fluorophenyl)-2-propenamide
  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

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.