((4-oxo-4H-chromen-3-yl)methyl)triphenylphosphonium bromide | 1186311-31-8

• 英文名称: ((4-oxo-4H-chromen-3-yl)methyl)triphenylphosphonium bromide
• CAS: 1186311-31-8
• 化学式: Br*C₂₈H₂₂O₂P
• 分子量: 501.359
• InChiKey: LSQKCRQYCDZKBE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ((4-oxo-4H-chromen-3-yl)methyl)triphenylphosphonium bromide 以 二氯甲烷 为溶剂， 以54%的产率得到3-((1E)-2-(4-oxo-4H-chromen-3-yl)vinyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and SAR studies of bis-chromenone derivatives for anti-proliferative activity against human cancer cells

  摘要：

  A novel family of 3-((4-oxo-4H-chromen-3-yl)methyl)-4H-chromen-4-one (bis-chromone) derivatives were designed, synthesized and studied for their anti-cancer activity using the XTT assay for the growth inhibition against various human cancer cells. Among them, 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-methoxy-4H-chromen-4-one and 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-hydroxy-4H-chromen-4-one showed micromolar level of in vitro anti-proliferative activity against human cancer cell lines. The SAR studies indicated bis-chromone as a basic scaffold to design anticancer agents. The 5-cyclohexylmethoxy on the first chromenone ring and electron donating group such as CH3, OCH3 or hydrogen bonding group (OH) on the other chromenone ring of bis-chromone increased the activity. However, saturation of one of chromenone to chromanone in bis-chromones decreased the activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.057
• 作为产物：
  描述：

  色酮-3-甲醛 在 aluminum oxide 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 ((4-oxo-4H-chromen-3-yl)methyl)triphenylphosphonium bromide
  参考文献：
  名称：

  Synthesis and SAR studies of bis-chromenone derivatives for anti-proliferative activity against human cancer cells

  摘要：

  A novel family of 3-((4-oxo-4H-chromen-3-yl)methyl)-4H-chromen-4-one (bis-chromone) derivatives were designed, synthesized and studied for their anti-cancer activity using the XTT assay for the growth inhibition against various human cancer cells. Among them, 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-methoxy-4H-chromen-4-one and 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-hydroxy-4H-chromen-4-one showed micromolar level of in vitro anti-proliferative activity against human cancer cell lines. The SAR studies indicated bis-chromone as a basic scaffold to design anticancer agents. The 5-cyclohexylmethoxy on the first chromenone ring and electron donating group such as CH3, OCH3 or hydrogen bonding group (OH) on the other chromenone ring of bis-chromone increased the activity. However, saturation of one of chromenone to chromanone in bis-chromones decreased the activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.057

文献信息

• Identification of a chromone-based retinoid containing a polyolefinic side chain via facile synthetic routes
  作者：Weilin Sun、Patrick J. Carroll、Dianne R. Soprano、Daniel J. Canney

  DOI：10.1016/j.bmcl.2009.05.081

  日期：2009.8

  Attempts to prepare substituted chromones as novel retinoids revealed that some chromones were unstable under Wadsworth-Horner-Emmons reaction conditions. Hence, Wittig reactions were used to prepare chromone-based compounds as potential retinoids. Firstly, Wittig reagents prepared from 3-bromomethyl-chromen-4-one were reacted with olefinic-aldehydes to provide the target compounds with all-trans side chains in good yield. The approach supplies a useful general route to structurally diverse chromone-based compounds possessing a variety of side chains. Sequential Wittig reactions were used also to prepare a chromone-based retinoid. These novel compounds were evaluated in binding assays and a high affinity RAR ligand was identified. Crystal structures obtained for two key precursors aided the interpretation of binding data. (C) 2009 Elsevier Ltd. All rights reserved.