6-hydroxyxanthenone-4-acetic acid methyl ester | 477192-12-4

• 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-hydroxyxanthenone-4-acetic acid methyl ester
• 英文别名: methyl 6-hydroxyxanthen-9-one-4-acetate；Methyl 2-(6-hydroxy-9-oxoxanthen-4-yl)acetate
• CAS: 477192-12-4
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: XIAWBEHIENSMMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-hydroxyxanthenone-4-acetic acid methyl ester 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 methyl (3,3-dimethyl-7-oxo-2,3-dihydro-1H,7H-4,12-dioxabenzo[a]anthracen-10-yl)acetate
  参考文献：
  名称：

  Synthesis and Antitumor Activity of New Derivatives of Xanthen-9-one-4-acetic Acid

  摘要：

  Xanthen-9-one-4-acetic acid (XAA) analogues in which the substituents in positions 5 and 6 are included in cyclic structures are described. Direct in vitro toxicity of the synthesized compounds against four tumor cell lines was evaluated, and their ability to stimulate mouse peritoneal macrophages and human monocytes in culture to become tumoricidal (indirect toxicity) was also studied. Despite low direct toxicity, almost all,the compounds proved to be able to significantly enhance the lytic properties of both murine macrophages and human monocytes. as well as the parent compound XAA and its most active derivative DMXAA taken as reference. In particular, compounds 4a, 5a, 7a, 13a,b, and 16a,b showed higher activity than the lead compound on human monocytes, compound 7a being 2.5 times more active than DMXAA, which is the most potent compound synthesized so far. Moreover, compounds 4a, 5a, 7a, 13a, 16a, and 16b proved to be able to induce TNF production in human immune cells.

  DOI：

  10.1021/jm020929p
• 作为产物：
  描述：

  3-chloro-5-methyl-9H-xanthen-9-one 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 吡啶盐酸盐 、 sodium 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 四氯化碳 、 乙醇 、 水 为溶剂， 反应 141.5h， 生成 6-hydroxyxanthenone-4-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis and Antitumor Activity of New Derivatives of Xanthen-9-one-4-acetic Acid

  摘要：

  Xanthen-9-one-4-acetic acid (XAA) analogues in which the substituents in positions 5 and 6 are included in cyclic structures are described. Direct in vitro toxicity of the synthesized compounds against four tumor cell lines was evaluated, and their ability to stimulate mouse peritoneal macrophages and human monocytes in culture to become tumoricidal (indirect toxicity) was also studied. Despite low direct toxicity, almost all,the compounds proved to be able to significantly enhance the lytic properties of both murine macrophages and human monocytes. as well as the parent compound XAA and its most active derivative DMXAA taken as reference. In particular, compounds 4a, 5a, 7a, 13a,b, and 16a,b showed higher activity than the lead compound on human monocytes, compound 7a being 2.5 times more active than DMXAA, which is the most potent compound synthesized so far. Moreover, compounds 4a, 5a, 7a, 13a, 16a, and 16b proved to be able to induce TNF production in human immune cells.

  DOI：

  10.1021/jm020929p

文献信息

• New derivatives of xanthenone-4-acetic acid: Synthesis, pharmacological profile and effect on TNF-α and NO production by human immune cells
  作者：Silvia Gobbi、Federica Belluti、Alessandra Bisi、Lorna Piazzi、Angela Rampa、Antonella Zampiron、Mariagnese Barbera、Anna Caputo、Maria Carrara

  DOI：10.1016/j.bmc.2006.02.003

  日期：2006.6

  New derivatives of xanthenone-4-acetic acid, bearing an alkoxy chain of variable length and a basic moiety, were synthesised in order to test the influence of this additional function on antitumour activity. The introduction of bulky substituents carrying a basic nitrogen seems to be somewhat tolerated, since for some of the compounds the enhancement of lytic potential of human monocytes was comparable to that of the reference molecule DMXAA. The induction of the release of TNF-alpha and nitric oxide by human monocytes, as well as the hypothesis of a potentiation of the activity of lipopolysaccharide in the induction of those cytotoxic factors, was also evaluated. In this respect, the most interesting compound (6a) exhibited the same spectrum of biological activity shown by DMXAA and seems therefore to be endowed with the same mechanism of action of the reference compound. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and Antitumor Activity of New Derivatives of Xanthen-9-one-4-acetic Acid
  作者：Silvia Gobbi、Angela Rampa、Alessandra Bisi、Federica Belluti、Piero Valenti、Anna Caputo、Antonella Zampiron、Maria Carrara

  DOI：10.1021/jm020929p

  日期：2002.10.1

  Xanthen-9-one-4-acetic acid (XAA) analogues in which the substituents in positions 5 and 6 are included in cyclic structures are described. Direct in vitro toxicity of the synthesized compounds against four tumor cell lines was evaluated, and their ability to stimulate mouse peritoneal macrophages and human monocytes in culture to become tumoricidal (indirect toxicity) was also studied. Despite low direct toxicity, almost all,the compounds proved to be able to significantly enhance the lytic properties of both murine macrophages and human monocytes. as well as the parent compound XAA and its most active derivative DMXAA taken as reference. In particular, compounds 4a, 5a, 7a, 13a,b, and 16a,b showed higher activity than the lead compound on human monocytes, compound 7a being 2.5 times more active than DMXAA, which is the most potent compound synthesized so far. Moreover, compounds 4a, 5a, 7a, 13a, 16a, and 16b proved to be able to induce TNF production in human immune cells.