6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one | 1135112-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one
• 英文别名: 6-(3,4,5-Trimethoxyphenyl)-6,7-dihydro[1,3]dioxolo[4,5-g]quinolin-8-ol；6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-[1,3]dioxolo[4,5-g]quinolin-8-one
• CAS: 1135112-27-4
• 化学式: C₁₉H₁₉NO₆
• 分子量: 357.363
• InChiKey: DHAJGKUFEDTMFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one 在 硫酸 、 sodium azide 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以75%的产率得到6-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro-9H-[1,3]dioxolo[4,5-h][1,4]benzodiazepin-9-one
  参考文献：
  名称：

  Schmidt重排介导的新型四氢-苯并[1,4]二氮杂-5-酮作为潜在的抗癌药和抗原生动物剂的合成

  摘要：

  通过施密特重排反应，由相应的1,2,3,4-tetrahydro-4合成了新颖的四氢-5 H-苯并[ e ] [1,4]二氮杂5-5-酮，其中几个含有喹啉药效团。NaN 3 / H 2 SO 4反应条件介导的喹诺酮类药物。美国国家癌症研究所（NCI）在体外筛选了十二种获得的化合物抑制60种不同人类肿瘤细胞系的能力，其中化合物24a对60种癌细胞系中的58种表现出显着的活性，其中最重要的是GI 50值范围从0.047至8.16μM和LC 50值范围从9.4到> 100μM。此外，其中一些被评估为抗疟药，抗锥虫病药和抗疟药。化合物22g 对恶性疟原虫的最佳抗疟疾反应为EC 50 = 13.61μg/ mL ，而化合物24d对克氏锥虫则表现出高活性。和Leishmania（V）panamensis的EC 50分别 为2.78μg/ mL和3.35μg/ mL。

  DOI：

  10.1016/j.ejmech.2017.10.024
• 作为产物：
  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

• A Schmidt rearrangement-mediated synthesis of novel tetrahydro-benzo[1,4]diazepin-5-ones as potential anticancer and antiprotozoal agents
  作者：Daniel Insuasty、Sara M. Robledo、Iván D. Vélez、Paola Cuervo、Braulio Insuasty、Jairo Quiroga、Manuel Nogueras、Justo Cobo、Rodrigo Abonia

  DOI：10.1016/j.ejmech.2017.10.024

  日期：2017.12

  NaN3/H2SO4 reaction conditions. Twelve of the obtained compounds were in vitro screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines, where compound 24a presented a remarkable activity against 58 of the 60 cancer cell lines, with the most important GI50 values ranging from 0.047 to 8.16 μM and LC50 values ranging from 9.4 to > 100 μM. Additionally

  通过施密特重排反应，由相应的1,2,3,4-tetrahydro-4合成了新颖的四氢-5 H-苯并[ e ] [1,4]二氮杂5-5-酮，其中几个含有喹啉药效团。NaN 3 / H 2 SO 4反应条件介导的喹诺酮类药物。美国国家癌症研究所（NCI）在体外筛选了十二种获得的化合物抑制60种不同人类肿瘤细胞系的能力，其中化合物24a对60种癌细胞系中的58种表现出显着的活性，其中最重要的是GI 50值范围从0.047至8.16μM和LC 50值范围从9.4到> 100μM。此外，其中一些被评估为抗疟药，抗锥虫病药和抗疟药。化合物22g 对恶性疟原虫的最佳抗疟疾反应为EC 50 = 13.61μg/ mL ，而化合物24d对克氏锥虫则表现出高活性。和Leishmania（V）panamensis的EC 50分别 为2.78μg/ mL和3.35μg/ mL。
• 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.