2,3,8,8a-四氢-7-(4-甲氧基苯基)-6-苯基-5(1H)-吲嗪酮 | 950567-39-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2,3,8,8a-四氢-7-(4-甲氧基苯基)-6-苯基-5(1H)-吲嗪酮
• 英文名称: 2,3,8,8a-Tetrahydro-7-(4-methoxyphenyl)-6-phenyl-5(1H)-indolizinone
• 英文别名: 7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one
• CAS: 950567-39-2
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: KQFPTEUZYOCIGQ-UHFFFAOYSA-N

物化性质

• 熔点：
  179-182℃
• 密度：
  1.21

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,8,8a-四氢-7-(4-甲氧基苯基)-6-苯基-5(1H)-吲嗪酮 在 三氯化硼 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到7-(4-hydroxyphenyl)-6-phenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-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
• 作为产物：
  描述：

  4'-methoxy-2-pyrrolidin-2-ylacetophenone 在 氢氧化钾 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 2,3,8,8a-四氢-7-(4-甲氧基苯基)-6-苯基-5(1H)-吲嗪酮
  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 and evaluation of heteroaromatic 6,7-diaryl-2,3,8,8a-tetrahydroindolizin-5(1H)-ones for cytotoxicity against the HCT-116 colon cancer cell line
  作者：F. Scott Kimball、Richard H. Himes、Gunda I. Georg

  DOI：10.1016/j.bmcl.2008.04.051

  日期：2008.6

  A heteroaromatic 6,7-diaryl-2,3,8,8a-tetrahydroindolizin-5(1H)-one analog library was prepared and tested for cytotoxic properties against the HCT-116 colon cancer cell line, thus providing additional information pertaining to structure-activity relationships for this class of compounds. The most active of the new analogs proved to be the C6 2-thiophene and 3-thiophene analogs with IC(50) values of

  制备了杂芳族 6,7-二芳基-2,3,8,8a-tetrahydroindolizin-5(1H)-one 类似物文库并测试其对 HCT-116 结肠癌细胞系的细胞毒性，从而提供有关结构的额外信息- 此类化合物的活性关系。最活跃的新类似物证明是 C6 2-噻吩和 3-噻吩类似物，IC(50) 值分别为 0.27 microM 和 0.60 microM。
• Enantiospecific synthesis and cytotoxicity of 7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one enantiomers
  作者：F. Scott Kimball、Brandon J. Turunen、Keith C. Ellis、Richard H. Himes、Gunda I. Georg

  DOI：10.1016/j.bmc.2008.02.073

  日期：2008.4

  An enantiospecific synthesis was developed to generate both enantiomers of 7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one. A biological assay utilizing the HCT-116 colon cancer cell line to determine the cytotoxicity of these analogs revealed that only the (R)-enantiomer exhibited appreciable cytotoxicity with an IC(50) value of 0.2 microM.

  开发了一种对映特异性合成来生成 7-(4-甲氧基苯基)-6-苯基-2,3,8,8a-四氢吲哚嗪-5(1H)-one 的两种对映异构体。利用 HCT-116 结肠癌细胞系来确定这些类似物的细胞毒性的生物测定表明，只有 (R)-对映体表现出明显的细胞毒性，IC(50) 值为 0.2 microM。
• 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.