(6,7-dimethoxy-2H-chromen-4-yl)(4-methoxy-2,2-dimethyl-2H-chromen-6-yl)methanone | 616207-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (6,7-dimethoxy-2H-chromen-4-yl)(4-methoxy-2,2-dimethyl-2H-chromen-6-yl)methanone
• 英文别名: (6,7-dimethoxy-2H-chromen-4-yl)(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)methanone；(6,7-dimethoxy-2H-chromen-4-yl)-(5-methoxy-2,2-dimethylchromen-6-yl)methanone
• CAS: 616207-43-3
• 化学式: C₂₄H₂₄O₆
• 分子量: 408.451
• InChiKey: YAVMWSNHCOMAMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6,7-dimethoxy-2H-chromen-4-yl)(4-methoxy-2,2-dimethyl-2H-chromen-6-yl)methanone 在 三氯化硼 、 potassium acetate 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 反应 2.0h， 以86%的产率得到cis-deguelin
  参考文献：
  名称：

  Concise Synthesis of the Chemopreventitive Agent (±)-Deguelin via a Key 6-Endo Hydroarylation

  摘要：

  [GRAPHIC]A concise total synthesis of (+/-)-deguelin was achieved with a longest linear sequence of six steps in 68% yield. A key step was the platinum-catalyzed 6-endo hydroarylation of an alkynone intermediate.

  DOI：

  10.1021/ol035419j
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 正丁基锂 、 溴 、 potassium carbonate 、 戴斯-马丁氧化剂 、 N,N-二乙基苯胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (6,7-dimethoxy-2H-chromen-4-yl)(4-methoxy-2,2-dimethyl-2H-chromen-6-yl)methanone
  参考文献：
  名称：

  Identification of small molecule inhibitors of the STAT3 signaling pathway: Insights into their structural features and mode of action

  摘要：

  A series of novel STAT3 inhibitors consisting of Michael acceptor has been identified through assays of the focused in-house library. In addition, their mode of action and structural feature responsible for the STAT3 inhibition were investigated. In particular, analog 6 revealed promising STAT3 inhibitory activity in HeLa cell lines. The analog also exhibited selective inhibition of STAT3 phosphorylation without affecting STAT1 phosphorylation and cytostatic effect in human breast epithelial cells (MCF10A-ras), which supports cancer cell-specific inhibitory properties. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.063

文献信息

• Alkyne Carbonyl Metathesis As a Means To Make 4-Acyl Chromenes: Syntheses of (±)-Deguelin and (±)-Munduserone
  作者：Maloy Nayak、Ikyon Kim

  DOI：10.1021/acs.joc.5b02160

  日期：2015.11.20

  A highly convergent synthetic approach to rotenoid natural products is described. Successful,pairing of two building blocks,for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready, access to 4-acylchromene, a key substructure of these natural products, leading to syntheses of (+/-)-degnelin and (+/-)-munduserone in high overall yields.
• NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：SNU R&DB Foundation

  公开号：EP2871187B1

  公开（公告）日：2017-09-20
• US9745280B2
  申请人：——

  公开号：US9745280B2

  公开（公告）日：2017-08-29
• Identification of small molecule inhibitors of the STAT3 signaling pathway: Insights into their structural features and mode of action
  作者：Kyeojin Kim、Su-Jung Kim、Young Taek Han、Sung-Jun Hong、Hongchan An、Dong-Jo Chang、Taewoo Kim、Bumhee Lim、Jeeyeon Lee、Young-Joon Surh、Young-Ger Suh

  DOI：10.1016/j.bmcl.2015.07.063

  日期：2015.11

  A series of novel STAT3 inhibitors consisting of Michael acceptor has been identified through assays of the focused in-house library. In addition, their mode of action and structural feature responsible for the STAT3 inhibition were investigated. In particular, analog 6 revealed promising STAT3 inhibitory activity in HeLa cell lines. The analog also exhibited selective inhibition of STAT3 phosphorylation without affecting STAT1 phosphorylation and cytostatic effect in human breast epithelial cells (MCF10A-ras), which supports cancer cell-specific inhibitory properties. (C) 2015 Elsevier Ltd. All rights reserved.
• Concise Synthesis of the Chemopreventitive Agent (±)-Deguelin via a Key 6-Endo Hydroarylation
  作者：Stefan J. Pastine、Dalibor Sames

  DOI：10.1021/ol035419j

  日期：2003.10.1

  [GRAPHIC]A concise total synthesis of (+/-)-deguelin was achieved with a longest linear sequence of six steps in 68% yield. A key step was the platinum-catalyzed 6-endo hydroarylation of an alkynone intermediate.