6,7-bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one | 76787-76-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 6,7-bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one
• 英文别名: 6,7-bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydro-1H-indolizin-5-one
• CAS: 76787-76-3
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: IWBAJYUYVTZPJH-UHFFFAOYSA-N

物化性质

• 沸点：
  599.4±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one 在 红铝 作用下， 以 甲苯 为溶剂， 以68 %的产率得到(+/-)-septicine
  参考文献：
  名称：

  通过酸催化酰亚胺离子电环化级联快速进入菲并吲哚里西啶生物碱

  摘要：

  采用一锅酸催化脱保护-缩合-电环化策略，实现了环代菲并吲哚里西啶生物碱的快速全合成。该合成路线仅用 4 步即可简洁地合成 (±)-seco-antofine 和 (±)-septicine，总产率分别为 22% 和 17%。

  DOI：

  10.1039/d3ob01359f
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙酰氯 在 氢氧化钾 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 6,7-bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one
  参考文献：
  名称：

  Synthesis, in vitro and in vivo cytotoxicity of 6,7-diaryl-2,3,8,8a-tetrahydroindolizin-5(1H)-ones

  摘要：

  A 6.7-diaryl-2,3.8.8a-tetrahydroindolizin-5(1H)-one library was constructed and tested against the colon cancer cell line HCT-116 as an initial screen for cytotoxic properties. Of this library, the parent compound, in which the southern aromatic ring remains unsubstituted, and the northern aromatic ring carries a 4-methoxy group, exhibited the most potent cytotoxicity with an IC50 value of 0.39 mu M and displayed promising activity in vivo in the NCI's mouse hollow fiber assay.(c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.103

文献信息

• Synthesis of (±)-septicine and (±)-tylophorine by regioselective [3 + 2] cycloaddition
  作者：Hideo Iida、Masao Tanaka、Chihiro Kibayashi

  DOI：10.1039/c39830000271

  日期：——

  The synthesis of (±)-septicine and (±)-tylophorine, using 1,3-dipolar cycloaddition and intramolecular photocyclisation reactions as key steps, is described.

  描述了使用1，3-偶极环加成和分子内光环化反应作为关键步骤的（±）-败血碱和（±）-酪氨酸的合成。
• Mangla, V. K.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 9, p. 748 - 749
  作者：Mangla, V. K.、Bhakuni, D. S.

  DOI：——

  日期：——
• Novel 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues as cytotoxic agents
  作者：Vedula M. Sharma、K.V. Adi Seshu、C. Vamsee Krishna、P. Prasanna、V. Chandra Sekhar、A. Venkateswarlu、Sriram Rajagopal、R. Ajaykumar、Dhanvanthri S. Deevi、N.V.S. Rao Mamidi、R. Rajagopalan

  DOI：10.1016/s0960-894x(03)00263-4

  日期：2003.5

  A series of 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues were synthesized and evaluated for cytotoxic activity against eight human cancer cell lines. Compounds 18, 21, 28, 29, 30 and 31 showed cytotoxic activity with GI(50) values in the range of 2.1-8.1 muM concentration. Among these, compounds 21 and 28 exhibited good pharmacokinetic properties. These compounds were further evaluated for their in vivo efficacy in modified hollow fibre assay (HFA). (C) 2003 Elsevier Science Ltd. All rights reserved.
• General synthesis of phenanthroindolizidine, phenanthroquinolizidine, and related alkaloids: preparation of (.+-.)-tylophorine, (.+-.)-cryptopleurine, (.+-.)-septicine, and (.+-.)-julandine
  作者：Hideo Iida、Yohya Watanabe、Masao Tanaka、Chihiro Kibayashi

  DOI：10.1021/jo00187a022

  日期：1984.6
• Synthesis, in vitro and in vivo cytotoxicity of 6,7-diaryl-2,3,8,8a-tetrahydroindolizin-5(1H)-ones
  作者：F. Scott Kimball、Ashok Rao Tunoori、Samuel F. Victory、Dinah Dutta、Jonathan M. White、Richard H. Himes、Gunda I. Georg

  DOI：10.1016/j.bmcl.2007.05.103

  日期：2007.8

  A 6.7-diaryl-2,3.8.8a-tetrahydroindolizin-5(1H)-one library was constructed and tested against the colon cancer cell line HCT-116 as an initial screen for cytotoxic properties. Of this library, the parent compound, in which the southern aromatic ring remains unsubstituted, and the northern aromatic ring carries a 4-methoxy group, exhibited the most potent cytotoxicity with an IC50 value of 0.39 mu M and displayed promising activity in vivo in the NCI's mouse hollow fiber assay.(c) 2007 Elsevier Ltd. All rights reserved.