2-(2-allyl-4-methylphenoxy)benzoic acid | 117571-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-allyl-4-methylphenoxy)benzoic acid
• 英文别名: 2-(4-methyl-2-prop-2-enylphenoxy)benzoic acid
• CAS: 117571-24-1
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: ZDFDAAOXBOTDLH-UHFFFAOYSA-N

物化性质

• 沸点：
  382.7±42.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-allyl-4-methylphenoxy)benzoic acid 在 polyphosphate ester 作用下， 反应 0.5h， 以66%的产率得到4-allyl-2-methylxanthenone
  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
• 作为产物：
  描述：

  邻氯苯甲酸钾 、 sodium 2-allyl-4-methylphenolate 在 三(3,6-二氧杂庚基)胺 、 copper(l) chloride 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 以47%的产率得到2-(2-allyl-4-methylphenoxy)benzoic 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

• Compounds having antitumor and antibacterial properties
  申请人：Cancer Research Campaign Technology Limited

  公开号：US05281620A1

  公开（公告）日：1994-01-25

  The novel class of xanthenone-4-acetic acids represented by the general formula (I) ##STR1## where R.sub.1 represents up to two of the groups lower alkyl, halogen, CF.sub.3, CN, NO.sub.2, NH.sub.2, CH.sub.2 COOH, OR.sub.2, OH, NHCOR.sub.2, NHSO.sub.2 R.sub.2, SR.sub.2, SO.sub.2 R.sub.2, CH.sub.2 CONHR.sub.2 or NHR.sub.2 (where R.sub.2 is lower alkyl optionally substituted with hydroxy, amino or methoxy functions), at any of the positions 1-8 which are available, R.sub.1 may also represent the substitution of an aza (--N.dbd.) group for one or two of the methine (--CH.dbd.) groups in the carbocyclic rings and two of R.sub.1 on any two available adjacent positions may also represent the grouping --CH.dbd.CH--CH.dbd.CH-- to form an additional fused benzene ring; and basic addition salts thereof, possess antitumour and antibacterial properties.

  通式（I）所代表的新型黄色素-4-乙酸类化合物，其中R.sub.1代表以下任意一个或两个基团：低碳链烷基，卤素，CF.sub.3，CN，NO.sub.2，NH.sub.2，CH.sub.2 COOH，OR.sub.2，OH，NHCOR.sub.2，NHSO.sub.2 R.sub.2，SR.sub.2，SO.sub.2 R.sub.2，CH.sub.2 CONHR.sub.2或NHR.sub.2（其中R.sub.2为低碳链烷基，可选地带有羟基，氨基或甲氧基功能），在可用的1-8位置中的任意位置。R.sub.1还可以代表将一个或两个亚胺（-N.dbd.）基团取代为碳环中的一个或两个甲烷（-CH.dbd.）基团，而在任意两个可用的相邻位置上的两个R.sub.1也可以代表群-CH.dbd.CH-CH.dbd.CH-以形成额外的融合苯环;以及其基本加成盐，具有抗肿瘤和抗菌性能。
• REWCASTLE, GORDON W.;ATWELL, GRAHAM J.;BAGULEY, BRUCE C.;CALVELEY, STEPHE+, J. MED. CHEM., 32,(1989) N, C. 793-799
  作者：REWCASTLE, GORDON W.、ATWELL, GRAHAM J.、BAGULEY, BRUCE C.、CALVELEY, STEPHE+

  DOI：——

  日期：——
• 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.