4-乙酰氨基苯-1,3-二羧酸 | 7501-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-乙酰氨基苯-1,3-二羧酸
• 英文名称: 4-acetamidoisophthalic acid
• 英文别名: 4-acetylamino-isophthalic acid；4-Acetylamino-isophthalsaeure；4-Acetamino-isophthalsaeure；4-Acetylaminoisophthalsaeure；4-Acetamidobenzene-1,3-dicarboxylic acid
• CAS: 7501-68-0
• 化学式: C₁₀H₉NO₅
• 分子量: 223.185
• InChiKey: KFABBSXAHCCRSK-UHFFFAOYSA-N

物化性质

• 熔点：
  295-296 °C (decomp)
• 沸点：
  544.6±45.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-乙酰氨基苯-1,3-二羧酸 在 硫酸 作用下， 生成 4-羟基间苯二甲酸
  参考文献：
  名称：

  Loewenherz, Chemische Berichte, 1892, vol. 25, p. 2797

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二甲基乙酰苯胺 在 calcium permanganate 、 水 作用下， 生成 4-乙酰氨基苯-1,3-二羧酸
  参考文献：
  名称：

  Ullmann; Uzbachian, Chemische Berichte, 1903, vol. 36, p. 1805

  摘要：

  DOI：

文献信息

• Pyrazolone–quinazolone hybrids: A novel class of human 4-hydroxyphenylpyruvate dioxygenase inhibitors
  作者：Yu-Ling Xu、Hong-Yan Lin、Run-Jie Cao、Ze-Zhong Ming、Wen-Chao Yang、Guang-Fu Yang

  DOI：10.1016/j.bmc.2014.08.011

  日期：2014.10

  4-Hydroxyphenylpyruvate dioxygenase (HPPD), converting 4-hydroxyphenylpyruvate acid to homogentisate, is an important target for treating type I tyrosinemia and alkaptonuria due to its significant role in tyrosine catabolism. However, only one commercial drug, NTBC, also known as nitisinone, has been available for clinical use so far. Herein, we have elucidated the structure-based design of a series of pyrazolone-quinazolone hybrids that are novel potent human HPPD inhibitors through the successful integration of various techniques including computational simulations, organic synthesis, and biochemical characterization. Most of the new compounds displayed potent inhibitory activity against the recombinant human HPPD in nanomolar range. Compounds 3h and 3u were identified as the most potent candidates with Ki values of around 10 nM against human HPPD, about three-fold more potent than NTBC. Molecular modeling indicated that the interaction between the pyrazolone ring and ferrous ion, and the hydrophobic interaction of quinazolone with its surrounding residues, such as Phe347 and Phe364, contributed greatly to the high potency of these inhibitors. Therefore, compounds 3h and 3u could be potentially useful for the treatment of type I tyrosinemia and other diseases with defects in tyrosine degradation.
• Reactions of amides with potassium permanganate in neutral aqueous solution
  作者：Chang Kiu Lee、Yu Mi Ahn

  DOI：10.1021/jo00276a045

  日期：1989.7
• Taub, Monatshefte fur Chemie, 1920, vol. 41, p. 141
  作者：Taub

  DOI：——

  日期：——
• Wegscheider; Malle; Ehrlich, Monatshefte fur Chemie, 1918, vol. 39, p. 394,395
  作者：Wegscheider、Malle、Ehrlich、Skutezky

  DOI：——

  日期：——
• Bogert; Wiggin; Sinclair, Journal of the American Chemical Society, 1907, vol. 29, p. 86
  作者：Bogert、Wiggin、Sinclair

  DOI：——

  日期：——