2-fluoro-6-(4-methylpiperazine-1-carbonyl)xanthen-9-one | 1222980-36-0

• 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: 2-fluoro-6-(4-methylpiperazine-1-carbonyl)xanthen-9-one
• CAS: 1222980-36-0
• 化学式: C₁₉H₁₇FN₂O₃
• 分子量: 340.354
• InChiKey: NTOLVJNZFXTZRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  53.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-fluoro-6-(4-methylpiperazine-1-carbonyl)xanthen-9-one 、 (3-methoxyphenyl)magnesium bromide 在 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到2-fluoro-6-(4-methylpiperazine-1-carbonyl)-9-hydroxy-9-(3-methoxyphenyl)-9H-xanthene
  参考文献：
  名称：

  Synthesis and cancer cell cytotoxicity of substituted xanthenes

  摘要：

  A series of substituted xanthenes was synthesized and screened for activity using DU-145, MCF-7, and HeLa cancer cell growth inhibition assays. The most potent compound, 9g ([N, N-diethyl]-9-hydroxy-9( 3-methoxyphenyl)-9H-xanthene-3-carboxamide), was found to inhibit cancer cell growth with IC50 values ranging from 36 to 50 mu M across all three cancer cell lines. Structure-activity relationship (SAR) data is presented that indicates additional gains in potency may be realized through further derivatization of the compounds (e. g., the incorporation of a 7-fluoro substituent to 9g). Results are also presented that suggest the compounds function through a unique mechanism of action as compared to that of related acridine and xanthone anticancer agents (which have been shown to intercalate into DNA and inhibit topoisomerase II activity). A structural comparison of these compounds suggests the differences in function may be due to the structure of the xanthene heterocycle which adopts a nonplanar conformation about the pyran ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.018
• 作为产物：
  描述：

  N-甲基哌嗪 、 以 二氯甲烷 为溶剂， 以0.28 g的产率得到2-fluoro-6-(4-methylpiperazine-1-carbonyl)xanthen-9-one
  参考文献：
  名称：

  Synthesis and cancer cell cytotoxicity of substituted xanthenes

  摘要：

  A series of substituted xanthenes was synthesized and screened for activity using DU-145, MCF-7, and HeLa cancer cell growth inhibition assays. The most potent compound, 9g ([N, N-diethyl]-9-hydroxy-9( 3-methoxyphenyl)-9H-xanthene-3-carboxamide), was found to inhibit cancer cell growth with IC50 values ranging from 36 to 50 mu M across all three cancer cell lines. Structure-activity relationship (SAR) data is presented that indicates additional gains in potency may be realized through further derivatization of the compounds (e. g., the incorporation of a 7-fluoro substituent to 9g). Results are also presented that suggest the compounds function through a unique mechanism of action as compared to that of related acridine and xanthone anticancer agents (which have been shown to intercalate into DNA and inhibit topoisomerase II activity). A structural comparison of these compounds suggests the differences in function may be due to the structure of the xanthene heterocycle which adopts a nonplanar conformation about the pyran ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.018