4-carboxymethyl-1-methyl-9-xanthenone | 88521-78-2

• 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-carboxymethyl-1-methyl-9-xanthenone
• 英文别名: (1-Methyl-9-oxo-9H-xanthen-4-yl)acetic acid；2-(1-methyl-9-oxoxanthen-4-yl)acetic acid
• CAS: 88521-78-2
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: BKKSSCGJZDSXJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2-[2-(Carboxymethyl)-5-methylphenoxy]benzoic acid 在 硫酸 作用下， 生成 4-carboxymethyl-1-methyl-9-xanthenone
  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

• Oxidation of 9-Xanthenones with Lead(IV) Acetate. Formation of Di-γ-lactones
  作者：Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1246/bcsj.56.2847

  日期：1983.9

  The oxidation of 9-xanthenones with lead(IV) acetate afforded 3a,3b,6a,12b-tetrahydro-2H-difuro[3,2-a:3′,2′-c]xanthene-2,5,7(3H,6H)-triones in addition to other products. Characterization of the di-γ-lactones and the difference between the oxidation reaction of lead(IV) and manganese(III) acetates in the 9-xanthenone system are discussed.

  用乙酸铅 (IV) 氧化 9-呫吨酮得到 3a,3b,6a,12b-四氢-2H-二呋喃 [3,2-a:3',2'-c]xanthene-2,5,7(3H ,6H)-triones 以及其他产品。讨论了二-γ-内酯的表征以及 9-呫吨酮系统中乙酸铅 (IV) 和乙酸锰 (III) 的氧化反应之间的差异。
• Compounds having antitumour and antibacterial properties
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0278176B1

  公开（公告）日：1994-03-09
• US5281620A
  申请人：——

  公开号：US5281620A

  公开（公告）日：1994-01-25
• [EN] ANTICANCER COMBINATION THERAPIES<br/>[FR] COMBINAISONS THÉRAPEUTIQUES ANTICANCERS
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2008024844A2

  公开（公告）日：2008-02-28

  [EN] Methods for treating or preventing hyperproliferating diseases, e.g., cancer, are described. A method may comprise administering to a subject in need thereof a therapeutically effective amount of a chemotherapeutic agent and a DNA vaccine.
  [FR] L'invention concerne des méthodes pour traiter ou prévenir des maladies hyperprolifératives, comme par exemple, un cancer. Une méthode peut comprendre l'administration d'une quantité thérapeutiquement efficace d'un agent chimiothérapeutique et d'un vaccin ADN à un sujet en ayant besoin.
• 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.