2-(4-chlorophenyl)-3-methyl-7,7-diphenyl-7,8-dihydropyrano[4,3-b]pyran-5(2H)-one | 1449584-20-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2-(4-chlorophenyl)-3-methyl-7,7-diphenyl-7,8-dihydropyrano[4,3-b]pyran-5(2H)-one
• 英文别名: 2-(4-Chlorophenyl)-3-methyl-7,7-diphenyl-2,8-dihydropyrano[4,3-b]pyran-5-one；2-(4-chlorophenyl)-3-methyl-7,7-diphenyl-2,8-dihydropyrano[4,3-b]pyran-5-one
• CAS: 1449584-20-6
• 化学式: C₂₇H₂₁ClO₃
• 分子量: 428.915
• InChiKey: TYRNTEKGDHXFKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-3-methyl-7,7-diphenyl-7,8-dihydropyrano[4,3-b]pyran-5(2H)-one 在 氧气 、 rose bengal 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88%的产率得到2-(4-chlorophenyl)-3-methyl-7,7-diphenyl-7,8-dihydro-2H-3,8a-epidioxypyrano[4,3-b]pyran-5(3H)-one
  参考文献：
  名称：

  Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures

  摘要：

  A novel series of 1,2,4-trioxanes were synthesized from 2H-pyrans via photooxidation, and their antiproliferative and growth factor inhibitory activity has been investigated across a variety of human cancer cell lines. Compounds 5k, 51, 5s, 7a and 7c exhibited the highest activity and selectivity against a human leukemia (MV4-11) cell line (IC50 = 0.5 mu M). Compound 5o showed the highest growth factor inhibitory activity against a melanoma (LOX-IMVI) cancer cell line (GI(50) = 1.0 mu M). A SAR study has confirmed the importance of the 1,2,4-trioxane unit as a pharmacophore for anticancer activity. The computer-assisted database analysis, COMPARE, has suggested that the compounds have unique mechanisms of actions that were different from those of known anticancer drugs. Some of the selected trioxanes were tested against the NF54 strain, albeit showing weak antiplasmodial activity. The molecular docking of trioxanes and hemin reveals that a short distance (130 angstrom) leads to their physical contact. The UV-vis spectroscopic analysis ensured the definite complexation between 1,2,4-trioxanes and hemin. The role of hemin-trioxane interaction in the hemin-induced oxidative damage has been studied using methylene blue as a substrate by UV-vis spectroscopy. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.008
• 作为产物：
  描述：

  二苯甲酮 在 sodium hydride 、 ethylenediamine Tetraacetic Acid 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 2-(4-chlorophenyl)-3-methyl-7,7-diphenyl-7,8-dihydropyrano[4,3-b]pyran-5(2H)-one
  参考文献：
  名称：

  Annulation of 2H-Pyran onto 1-Oxa- or 1-Azacyclohexane-2,4-diones and Their Analogues via Sequential Condensation with α-Substituted Enals and 6π-Electrocyclization

  摘要：

  通过Knoevenagel缩合反应与烯醛反应，随后进行6π-电环化反应，以1-氧杂-或1-氮杂环己烷-2,4-二酮为核心构建了2H-吡喃衍生物，这些反应易于用乙二胺二乙酸盐催化。这种形式上的[3 + 3]策略构成了C–O和C–C键的形成，并通过在1-氧杂环己烷-2,4-二酮中使用相同的芳基进行6,6-二取代来避免立体异构体的形成。这种简便的方法学极大地促进了多取代双环2H-吡喃的合成，具有多样化的底物选择和产品稳定性的提高。

  DOI：

  10.1246/bcsj.20130069

文献信息

• Annulation of 2<i>H</i>-Pyran onto 1-Oxa- or 1-Azacyclohexane-2,4-diones and Their Analogues via Sequential Condensation with α-Substituted Enals and 6π-Electrocyclization
  作者：Md. Imran Hossain、Elkhabiry Shaban、Taku Ikemi、Wei Peng、Hiroyuki Kawafuchi、Tsutomu Inokuchi

  DOI：10.1246/bcsj.20130069

  日期：2013.7.15

  2H-Pyrans are constructed on a 1-oxa- or 1-azacyclohexane-2,4-dione core via Knoevenagel condensation with enals followed by 6π-electrocyclization, which are readily catalyzed with ethylenediammonium diacetate. This formal [3 + 3] strategy constitutes C–O and C–C bond making and the diastereomer formation is circumvented using 6,6-disubstitution with the same aryl group in the 1-oxacyclohexane-2,4-diones. This facile methodology significantly advances the access to polysubstituted bicyclic 2H-pyrans with a versatile substrate choice and improved stability of the product.

  通过Knoevenagel缩合反应与烯醛反应，随后进行6π-电环化反应，以1-氧杂-或1-氮杂环己烷-2,4-二酮为核心构建了2H-吡喃衍生物，这些反应易于用乙二胺二乙酸盐催化。这种形式上的[3 + 3]策略构成了C–O和C–C键的形成，并通过在1-氧杂环己烷-2,4-二酮中使用相同的芳基进行6,6-二取代来避免立体异构体的形成。这种简便的方法学极大地促进了多取代双环2H-吡喃的合成，具有多样化的底物选择和产品稳定性的提高。
• Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures
  作者：Md. Imran Hossain、Marta Świtalska、Wei Peng、Mariko Takashima、Ning Wang、Marcel Kaiser、Joanna Wietrzyk、Shingo Dan、Takao Yamori、Tsutomu Inokuchi

  DOI：10.1016/j.ejmech.2013.08.008

  日期：2013.11

  A novel series of 1,2,4-trioxanes were synthesized from 2H-pyrans via photooxidation, and their antiproliferative and growth factor inhibitory activity has been investigated across a variety of human cancer cell lines. Compounds 5k, 51, 5s, 7a and 7c exhibited the highest activity and selectivity against a human leukemia (MV4-11) cell line (IC50 = 0.5 mu M). Compound 5o showed the highest growth factor inhibitory activity against a melanoma (LOX-IMVI) cancer cell line (GI(50) = 1.0 mu M). A SAR study has confirmed the importance of the 1,2,4-trioxane unit as a pharmacophore for anticancer activity. The computer-assisted database analysis, COMPARE, has suggested that the compounds have unique mechanisms of actions that were different from those of known anticancer drugs. Some of the selected trioxanes were tested against the NF54 strain, albeit showing weak antiplasmodial activity. The molecular docking of trioxanes and hemin reveals that a short distance (130 angstrom) leads to their physical contact. The UV-vis spectroscopic analysis ensured the definite complexation between 1,2,4-trioxanes and hemin. The role of hemin-trioxane interaction in the hemin-induced oxidative damage has been studied using methylene blue as a substrate by UV-vis spectroscopy. (C) 2013 Elsevier Masson SAS. All rights reserved.