3-(4-Chlorophenyl)-1-(6-hydroxy-4,7-dimethoxybenzofuran-5-yl)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: 3-(4-Chlorophenyl)-1-(6-hydroxy-4,7-dimethoxybenzofuran-5-yl)prop-2-en-1-one
• 英文别名: (E)-3-(4-chlorophenyl)-1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)prop-2-en-1-one
• 化学式: C₁₉H₁₅ClO₅
• 分子量: 358.778
• InChiKey: VLYKEIDXUZVLGR-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-Chlorophenyl)-1-(6-hydroxy-4,7-dimethoxybenzofuran-5-yl)prop-2-en-1-one 在 吡啶 、 sodium hydroxide 、 双氧水 作用下， 以 水 为溶剂， 反应 96.0h， 以65%的产率得到2-[(4-chlorophenyl)methylidene]-4,8-dimethoxyfuro[3,2-f][1]benzofuran-3-one
  参考文献：
  名称：

  菲醌与一些来自 KHELLIN 和 VISNAGIN 的新 aurones 的光化学反应

  摘要：

  摘要 菲醌 2 和 aurones 5a-h 有可能发生有趣的光化学反应，导致形成加合物 6a-h。1,4-二恶英衍生物 6a-h 的结构是在分析数据和光谱证据的基础上确定的。

  DOI：

  10.1081/scc-120003624
• 作为产物：
  描述：

  凯林 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 3-(4-Chlorophenyl)-1-(6-hydroxy-4,7-dimethoxybenzofuran-5-yl)prop-2-en-1-one
  参考文献：
  名称：

  菲醌与一些来自 KHELLIN 和 VISNAGIN 的新 aurones 的光化学反应

  摘要：

  摘要 菲醌 2 和 aurones 5a-h 有可能发生有趣的光化学反应，导致形成加合物 6a-h。1,4-二恶英衍生物 6a-h 的结构是在分析数据和光谱证据的基础上确定的。

  DOI：

  10.1081/scc-120003624

文献信息

• Khellinone Derivatives as Blockers of the Voltage-Gated Potassium Channel Kv1.3:  Synthesis and Immunosuppressive Activity
  作者：Jonathan B. Baell、Robert W. Gable、Andrew J. Harvey、Nathan Toovey、Tanja Herzog、Wolfram Hänsel、Heike Wulff

  DOI：10.1021/jm030523s

  日期：2004.4.1

  The voltage-gated potassium channel Kv1.3 constitutes a promising new target for the treatment of T-cell-mediated autoimmune diseases such as multiple sclerosis. In this study, we report the discovery of two new classes of Kv1.3 blockers based on the naturally occurring compound khellinone, 5-acetyl-4,7-dimethoxy-6-hydroxybeiizofuran: (1) khellinone dimers linked via the alkylation of the 6-hydroxy groups and (2) chalcone derivatives of khellinone formed by Claisen-Schmidt condensation of the 5-acetyl group with aryl aldehydes. In particular, the chalcone 3-(4,7-dimethoxy-6-hydroxybenzofuran-5-yl)-1-phenyl-3-oxopropene (16) and several of its derivatives inhibited Kv1.3 with K-d values of 300-800 nM and a Hill coefficient of 2, displayed moderate selectivity over other Kv1-family K+ channels, suppressed T-lymphocyte proliferation at submicromolar concentrations, and showed no signs of acute toxicity in mice. Because of their relatively low molecular weight and lipophilicity and their high affinity to Kv1.3, aryl-substituted khellinone derivatives represent attractive lead compounds for the development of more potent and selective Kv1.3 blocking immunosuppressants.
• HAFEZ, O. M. ABDHL;AHMED, K. M.;MANDOUR, A. M.;EL-KHRISY, E. A. M., PAKISTAN J. SCI. AND IND. RES., 33,(1990) N-6, C. 197-200
  作者：HAFEZ, O. M. ABDHL、AHMED, K. M.、MANDOUR, A. M.、EL-KHRISY, E. A. M.

  DOI：——

  日期：——
• FURANOCHALCONES AS INHIBITORS OF CYP1A1, CYP1A2 AND CYP1B1 FOR CANCER CHEMOPREVENTION
  申请人：Council of Scientific & Industrial Research

  公开号：US20210284618A1

  公开（公告）日：2021-09-16

  The present invention relates to the furanochalcone class of compounds of general formula A. The present invention particularly relates to the synthesis of furanochalcones and their CYP1A1, CYP1A2 and CYP1B1 inhibitory activity. In addition, the invention relates to the prevention or treatment of cancer caused by polyaromatic hydrocarbons (PAHs), 4-nitroquinoline-1-oxide, and N-nitroso-N-methylurea, heterocyclic amines, estrogen and 17β-estradiol, resulting from the inhibition of CYP1A1, CYP1A2 and CYP1B1 enzymes.
• Thionation of Chalcone and Aurone Derivatives by Lawesson's Reagent
  作者：Eman Elhefny

  DOI：10.1080/10426507.2012.704457

  日期：2013.6.1

  The reaction of Lawesson's reagent (LR 5) with chalcones (4a-h) and aurones (12a-h) proceeds in refluxing toluene to give the respective benzofuranylprop-2-en-1-thiones (8a-h) and benzodifuran-3-thiones (13a-h). Correct elemental analyses and spectroscopic data were obtained for the new compounds.
• PHOTOCHEMICAL REACTION OF PHENANTHRENEQUINONE WITH SOME NEW AURONES DERIVED FROM KHELLIN AND VISNAGIN
  作者：A. A. Nada、M. F. Zayed、N. Khir El Din、M. M. T. El-Saidi、E. Hefny

  DOI：10.1081/scc-120003624

  日期：2002.1

  ABSTRACT Phenanthrenequinone 2 and aurones 5a–h are potentially capable of undergoing an interesting photochemical reaction leading to the formation of the adducts 6a–h. The structures of the 1,4-dioxine derivatives 6a–h were firmly established on the basis of analytical data and spectroscopic evidences.

  摘要 菲醌 2 和 aurones 5a-h 有可能发生有趣的光化学反应，导致形成加合物 6a-h。1,4-二恶英衍生物 6a-h 的结构是在分析数据和光谱证据的基础上确定的。