(9-oxo-9H-xanthen-3-yl)acetic acid | 118537-75-0

• 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: (9-oxo-9H-xanthen-3-yl)acetic acid
• 英文别名: xanthone-3-acetic acid；3-xanthoneacetic acid；(xanthon-3-yl)acetic acid；2-(9-Oxoxanthen-3-yl)acetic acid
• CAS: 118537-75-0
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: SUPAWMOOSGYVIR-UHFFFAOYSA-N

物化性质

• 熔点：
  227.5-228.5 °C
• 沸点：
  498.1±34.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-methyl-9H-xanthen-9-one 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 水 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 水 为溶剂， 生成 (9-oxo-9H-xanthen-3-yl)acetic acid
  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

• Photodecarboxylation of Xanthone Acetic Acids:  C−C Bond Heterolysis from the Singlet Excited State
  作者：Jessie A. Blake、Eric Gagnon、Matthew Lukeman、J. C. Scaiano

  DOI：10.1021/ol052953d

  日期：2006.3.1

  products, consistent with an intermediate benzylic carbanion. Fluorescence and laser flash photolysis (LFP) studies suggest singlet state reactivity, which is unusual for aromatic ketones. 3-Xanthone acetic acid is photoinert under the same conditions. The results suggest that the reactive xanthone acetic acids are promising precursors for carbanion-mediated photocages.

  [反应：见正文]在含水缓冲液（pH 7.4）中辐照2-和4-蒽酮乙酸可导致有效的脱羧作用（分别为Phi = 0.67和0.64），得到相应的甲基产物，与中间的苄基碳负离子相符。荧光和激光闪光光解（LFP）研究表明，单重态反应性对于芳香族酮是不常见的。3-X吨酮乙酸在相同条件下是光惰性的。结果表明，反应性x吨酮乙酸是碳负离子介导的光笼的前体。
• US20140275316A1
  申请人：——

  公开号：US20140275316A1

  公开（公告）日：2014-09-18
• US9637565B2
  申请人：——

  公开号：US9637565B2

  公开（公告）日：2017-05-02
• Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo
  作者：Gordon W. Rewcastle、Graham J. Atwell、Bruce C. Baguley、Stephen B. Calveley、William A. Denny

  DOI：10.1021/jm00124a012

  日期：1989.4

  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.