1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₉H₁₉NO₆
• 分子量: 357.363
• InChiKey: MJOSDWMVKKYJJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 对甲苯磺酸 作用下， 以 异丙醇 为溶剂， 反应 1.8h， 以74%的产率得到6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one
  参考文献：
  名称：

  Conformational and configurational disorder in 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one and 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8-one: a hydrogen-bonded chain of rings and π-stacked hydrogen-bonded chains

  摘要：

  In 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one, C19H19NO6, (I), the six-membered heterocyclic ring adopts a conformation intermediate between envelope and half-chair forms; it is disordered over two enantiomeric configurations, with occupancies of 0.879 (3) and 0.121 (3), leading to positional disorder of the 3,4,5-trimethoxyphenyl unit. In 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g] quinolin-8-one, C17H13NO5, (II), the molecules are similarly disordered, with occupancies of 0.866 (4) and 0.134 (4). The molecules in (I) are linked by one three-centre N-H center dot center dot center dot(O)(2) hydrogen bond and one two-centre C-H center dot center dot center dot O hydrogen bond to form a complex chain of rings whose formation is reinforced by two independent aromatic pi-pi stacking interactions. In (II), a single N-H center dot center dot center dot O hydrogen bond links the molecules into a simple chain, and pairs of chains are linked by a single aromatic pi-pi stacking interaction.

  DOI：

  10.1107/s0108270109019556

文献信息

• MATTER OF COMPOSITION, SYNTHESIS, FORMULATION AND APPLICATION OF FL118 PLATFORM POSITIONS 7 AND 9-DERIVED ANALOGUES FOR TREATMENT OF HUMAN DISEASE
  申请人：Canget BioTekpharma

  公开号：US20200231596A1

  公开（公告）日：2020-07-23

  Described herein, are the chemical synthesis, matter of compositions, formulation, function, methods and uses of the FL118 platform Positions 7 and/or 9-derived analogues for treating cancer or other human diseases. Compounds derived from chemical modifications of the FL118 platform are employed alone or in combination with other anti-cancer agents to preclude, eliminate or reverse cancer phenotypes. This invention intends to realize unique personalized cancer treatment (personalized precision medicine) through application of a series of structural relevant individual FL118 platform-derived analogues, which target multiple cellular human disease-relevant proteins and their signaling pathways.
• Conformational and configurational disorder in 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5<i>H</i>-1,3-dioxolo[4,5-<i>g</i>]quinolin-8(5<i>H</i>)-one and 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5<i>H</i>-1,3-dioxolo[4,5-<i>g</i>]quinolin-8-one: a hydrogen-bonded chain of rings and π-stacked hydrogen-bonded chains
  作者：Paola Cuervo、Rodrigo Abonía、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270109019556

  日期：2009.7.15

  In 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one, C19H19NO6, (I), the six-membered heterocyclic ring adopts a conformation intermediate between envelope and half-chair forms; it is disordered over two enantiomeric configurations, with occupancies of 0.879 (3) and 0.121 (3), leading to positional disorder of the 3,4,5-trimethoxyphenyl unit. In 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g] quinolin-8-one, C17H13NO5, (II), the molecules are similarly disordered, with occupancies of 0.866 (4) and 0.134 (4). The molecules in (I) are linked by one three-centre N-H center dot center dot center dot(O)(2) hydrogen bond and one two-centre C-H center dot center dot center dot O hydrogen bond to form a complex chain of rings whose formation is reinforced by two independent aromatic pi-pi stacking interactions. In (II), a single N-H center dot center dot center dot O hydrogen bond links the molecules into a simple chain, and pairs of chains are linked by a single aromatic pi-pi stacking interaction.