ethyl ((13aS,14S)-14-hydroxy-6,7-dimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-3-yl) carbonate | 1223487-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: ethyl ((13aS,14S)-14-hydroxy-6,7-dimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-3-yl) carbonate
• 英文别名: carbonic acid ethyl ester (12aS,13S)-13-hydroxy-6,7-dimethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene-3-yl ester；carbonic acid ethyl ester(12aS,13S)-13-hydroxy-6,7-dimethoxy-9,10,11,12,12a,13-hexahydro-9a-azacyclopenta[b]triphenylene-3-yl ester；[(13aS,14S)-14-hydroxy-6,7-dimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-3-yl] ethyl carbonate
• CAS: 1223487-80-6
• 化学式: C₂₅H₂₇NO₆
• 分子量: 437.492
• InChiKey: MGUNQOGGSXPJAJ-GBXCKJPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  氯甲酸乙酯 、 13a(S),14(S)-(+)-3,14-dihydroxy-6,7-dimethoxyphenanthroindolizidine 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以52.3%的产率得到ethyl ((13aS,14S)-14-hydroxy-6,7-dimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-3-yl) carbonate
  参考文献：
  名称：

  Synthesis of Phenanthroindolizidine Alkaloids with an Acyloxy Group at the C3 Position and their Antitumor Activities and Toxicities

  摘要：

  我们之前报告过，苯并吲哚烯醇真碱3及其衍生物在体外具有显著的细胞毒性。然而，它们在体内的抗肿瘤活性较低且毒性较高，这对进一步开发构成了严重问题。基于通过乙酰化3可以改善抗肿瘤活性和毒性的发现，我们合成了3的新衍生物，这些衍生物具有不同的酰基，并评估了它们的抗肿瘤活性和毒性。我们发现，具有立体较小酰基的衍生物的抗肿瘤活性得到了改善。

  DOI：

  10.2174/157018012800389232

文献信息

• PHENANTHROINDOLIZIDINE DERIVATIVE AND NFKB INHIBITOR CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：Ikeda Takashi

  公开号：US20110201637A1

  公开（公告）日：2011-08-18

  A novel compound having an excellent NFκB inhibitory effect is provided. Specifically disclosed is a compound represented by the following formula (1) or a salt thereof: wherein, R 1 represents a hydrogen atom, a lower alkyl group, or the like; R 2 represents a hydrogen atom, a lower alkyl group, a halogen atom, or the like; R 3 represents a hydrogen atom, a lower alkyl group, a hydroxyl group, or a halogen atom; R 4 represents a hydrogen atom or a lower alkyloxy group; R 5 represents a hydrogen atom, a lower alkyloxy group, a halogen atom, a hydroxyl group, or a methylenedioxy group formed together with R 6 or an isopropylidenedioxy group formed together with R 6 ; R 6 represents a hydrogen atom, a lower alkyloxy group, or a methylenedioxy group formed together with R 5 or an isopropylidenedioxy group formed together with R 5 ; R 7 represents a hydrogen atom or a lower alkyl group; and R 8 represents a hydrogen atom, a hydroxyl group, an amino group, a lower alkylcarbonyloxy group, or a halogen atom.

  提供一种具有优异的NFκB抑制效果的新化合物。具体披露的是以下式（1）或其盐的化合物：其中，R1代表氢原子，低碳基或类似物; R2代表氢原子，低碳基，卤素原子或类似物; R3代表氢原子，低碳基，羟基或卤素原子; R4代表氢原子或低碳基氧基; R5代表氢原子，低碳基氧基，卤素原子，羟基或与R6形成的亚甲二氧基或与R6形成的异丙亚甲基二氧基; R6代表氢原子，低碳基氧基或与R5形成的亚甲二氧基或与R5形成的异丙亚甲基二氧基; R7代表氢原子或低碳基; R8代表氢原子，羟基，氨基，低碳基羰基氧基或卤素原子。
• PHENANTHROINDOLIZIDINE DERIVATIVE AND NF B INHIBITOR CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：Kabushiki Kaisha Yakult Honsha

  公开号：EP2351753A1

  公开（公告）日：2011-08-03

  A novel compound having an excellent NFκB inhibitory effect is provided. Specifically disclosed is a compound represented by the following formula (1) or a salt thereof: wherein, R1 represents a hydrogen atom, a lower alkyl group, or the like; R2 represents a hydrogen atom, a lower alkyl group, a halogen atom, or the like; R3 represents a hydrogen atom, a lower alkyl group, a hydroxyl group, or a halogen atom; R4 represents a hydrogen atom or a lower alkyloxy group; R5 represents a hydrogen atom, a lower alkyloxy group, a halogen atom, a hydroxyl group, or a methylenedioxy group formed together with R6 or an isopropylidenedioxy group formed together with R6; R6 represents a hydrogen atom, a lower alkyloxy group, or a methylenedioxy group formed together with R5 or an isopropylidenedioxy group formed together with R5; R7 represents a hydrogen atom or a lower alkyl group; and R8 represents a hydrogen atom, a hydroxyl group, an amino group, a lower alkylcarbonyloxy group, or a halogen atom.

  本研究提供了一种具有优异 NFκB 抑制作用的新型化合物。具体公开了由下式（1）代表的化合物或其盐： 其中，R1 代表氢原子、低级烷基或类似物； R2 代表氢原子、低级烷基、卤素原子或类似物； R3 代表氢原子、低级烷基、羟基或卤素原子； R4 代表氢原子或低级烷氧基； R5 代表氢原子、低级烷氧基、卤素原子、羟基或与 R6 共同形成的亚甲基二氧基或与 R6 共同形成的亚异丙基二氧基； R6 代表氢原子、低级烷氧基或与 R5 共同形成的亚甲基二氧基或与 R5 共同形成的亚异丙基二氧基； R7 代表氢原子或低级烷基；以及 R8 代表氢原子、羟基、氨基、低级烷基羰氧基或卤原子。
• PHENANTHROINDOLIZIDINE DERIVATIVE AND NF kB INHIBITOR CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：Kabushiki Kaisha Yakult Honsha

  公开号：EP2351753B1

  公开（公告）日：2015-02-11
• US8569327B2
  申请人：——

  公开号：US8569327B2

  公开（公告）日：2013-10-29