4-bromomethyl-3-chloro-xanthen-9-one | 43160-06-1

• 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: 4-bromomethyl-3-chloro-xanthen-9-one
• 英文别名: 4-(Bromomethyl)-3-chloroxanthen-9-one
• CAS: 43160-06-1
• 化学式: C₁₄H₈BrClO₂
• 分子量: 323.573
• InChiKey: WAEBOVPYZAPKIE-UHFFFAOYSA-N

物化性质

• 熔点：
  175-178 °C
• 沸点：
  462.0±45.0 °C(Predicted)
• 密度：
  1.658±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromomethyl-3-chloro-xanthen-9-one 在 tetra(n-butyl)ammonium dichromate(VI) 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 15.0h， 生成 3-O-methyl 5-O-prop-2-enyl 4-(3-chloro-9-oxoxanthen-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Bisi, Alessandra; Budriesi, Roberta; Rampa, Angela, Arzneimittel-Forschung/Drug Research, 1996, vol. 46, # 9, p. 848 - 851

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium 3-chloro-2-methylphenolate 在 N-溴代丁二酰亚胺(NBS) 、 polyphosphate ester 、 三(3,6-二氧杂庚基)胺 、 copper(l) chloride 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 生成 4-bromomethyl-3-chloro-xanthen-9-one
  参考文献：
  名称：

  Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo

  摘要：

  In a search for compounds related to flavoneacetic acid with activity against solid tumors, a series of methyl-, methoxy-, chloro-, nitro-, and hydroxy-substituted xanthenone-4-acetic acids have been synthesized and evaluated against subcutaneously implanted colon adenocarcinoma 38 in vivo, using a short-term histology assay as a primary screening system. A major goal of this work was to identify compounds with similar profiles of activity to that of flavoneacetic acid but of higher potency. The level of activity of the compounds appeared to depend more on the nature of the substituent than its positioning, in the order Cl greater than Me, OMe greater than NO2, OH. However, the potency of the compounds was related much more to the position rather than the nature of the substitution, with 5-substituted compounds being clearly the most dose potent. 5-Methylxanthenone-4-acetic acid has a similar level of activity to that of flavoneacetic acid in the test systems employed but is more than 7-fold as dose potent.

  DOI：

  10.1021/jm00124a012

文献信息

• Da Re,P. et al., Chimica Therapeutica, 1973, vol. 8, p. 60 - 64
  作者：Da Re,P. et al.

  DOI：——

  日期：——