N,N-diethyl-N'-(o-carboxyphenyl)urea | 233684-03-2

• 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: N,N-diethyl-N'-(o-carboxyphenyl)urea
• 英文别名: 2-(3,3-diethylureido)benzoic acid；N-diethylcarbamoyl-anthranilic acid；N-Diaethylcarbamoyl-anthranilsaeure；2-(diethylcarbamoylamino)benzoic acid
• CAS: 233684-03-2
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: PYYMHUIREWOXKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-N'-(o-carboxyphenyl)urea 在 盐酸 作用下， 反应 0.17h， 生成 靛红酸酐
  参考文献：
  名称：

  N-(甲磺酰氧基)邻苯二甲酰亚胺与仲胺的一锅反应生成2-脲基苯甲酰胺、2-脲基苯甲酸、2-脲基苯甲酸乙酯或Isatoic酸酐。

  摘要：

  研究了 N-(甲磺酰氧基)邻苯二甲酰亚胺与仲胺的反应。转化通过一锅反应完成，以任选地分别提供相应的 2-脲基苯甲酰胺、2-脲基苯甲酸、2-脲基苯甲酸乙酯或靛红酸酐。讨论了中间体 2-脲基苯甲酰胺酸催化水解（或醇解）为 2-脲基苯甲酸（或酯）的机理。提出了涉及脲基部分作为内部酸催化剂的质子转移机制。中间体 2-脲基苯甲酸进一步转化为靛红酸酐。证明了利用所获得的 2-ureidobenzamides、2-ureidobenzoic 酸和 2-ureidobenzoate 来制备 3,1-benzoxazin-4-ones。

  DOI：

  10.1021/jo9900634
• 作为产物：
  描述：

  2-(diethylamino)-4H-benzo[d][1,3]oxazin-4-one 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 408.0h， 生成 N,N-diethyl-N'-(o-carboxyphenyl)urea
  参考文献：
  名称：

  N-(甲磺酰氧基)邻苯二甲酰亚胺与仲胺的一锅反应生成2-脲基苯甲酰胺、2-脲基苯甲酸、2-脲基苯甲酸乙酯或Isatoic酸酐。

  摘要：

  研究了 N-(甲磺酰氧基)邻苯二甲酰亚胺与仲胺的反应。转化通过一锅反应完成，以任选地分别提供相应的 2-脲基苯甲酰胺、2-脲基苯甲酸、2-脲基苯甲酸乙酯或靛红酸酐。讨论了中间体 2-脲基苯甲酰胺酸催化水解（或醇解）为 2-脲基苯甲酸（或酯）的机理。提出了涉及脲基部分作为内部酸催化剂的质子转移机制。中间体 2-脲基苯甲酸进一步转化为靛红酸酐。证明了利用所获得的 2-ureidobenzamides、2-ureidobenzoic 酸和 2-ureidobenzoate 来制备 3,1-benzoxazin-4-ones。

  DOI：

  10.1021/jo9900634

文献信息

• Aromatic 2-(Thio)ureidocarboxylic Acids As a New Family of Modulators of Multidrug Resistance-Associated Protein 1: Synthesis, Biological Evaluation, and Structure−Activity Relationships
  作者：Hans-Georg Häcker、Stefan Leyers、Jeanette Wiendlocha、Michael Gütschow、Michael Wiese

  DOI：10.1021/jm900688v

  日期：2009.8.13

  Four series of aromatic carboxylic acids were prepared with a urea or thiourea moiety at the neighboring position to the carboxyl group and benzene or thiophene as aromatic scaffold. Using a calcein AM assay, these compounds were evaluated as inhibitors of multidrug resistance-associated protein I (MRP1) and selected compounds were examined toward P-glycoprotein (P-gp) as well as breast cancer resistance protein (BCRP) to assess selectivity for MRP1. Two 2-thioureidobenzo[b]-thiophene-3-carboxylic acids (48, 49) were identified as particularly potent inhibitors of MRP1, with IC50 values of around 1 mu M. The structural features of this new family or nontoxic MRP1 inhibitors include a (thio)urea disubstituted with preferentially two alkyl groups at the terminal nitrogen and an additional fused aromatic ring.
• Antidepressant activity of carbamates and urea derivatives
  作者：Shahnaz Perveen、Nasreen Fatima、Muhammad Aitmaud Khan、Ahsana Dar、Khalid M. Khan、Nighat Afza、Wolfgang Voelter

  DOI：10.1007/s00044-011-9797-8

  日期：2012.9

  Thirteen (13) compounds of N-phenyl-O-alkyl carbamates (1 and 3), N,N-diethyl-N'-alkyl/aryl/phenylpiperazinoureas (4-6, 8-12), N-phenyl-N'-phenylpiperazino/imidazoureas (2, 7), and N-ethyl-(N'-phenylpiperazino) thioureas 13 were synthesized and tested for their antidepressant-like activity in mice. It was found that compound N-phenyl-O-heptyl carbamate 1 and N-phenyl-N'-phenylpiperazinourea 2 showed 32.5 and 27.7% antidepressant activity in the forced swim test in mice, respectively. Considering other carbamates it was found that a decrease in alkyl chain length caused a marked decline in the antidepressant activity. Compounds 1-4 show even higher activities in the forced swim test than the standard phenelzine.
• Perveen, Shahnaz; Fatima, Nasreen; Khan, Khalid Mohammed, Journal of the Chemical Society of Pakistan, 2010, vol. 32, # 3, p. 338 - 343
  作者：Perveen, Shahnaz、Fatima, Nasreen、Khan, Khalid Mohammed、Khan, Ajmal、Ali, Muhammad、Choudhary, Muhammad Iqbal

  DOI：——

  日期：——
• One-Pot Reactions of <i>N</i>-(Mesyloxy)phthalimides with Secondary Amines to 2-Ureidobenzamides, 2-Ureidobenzoic Acids, Ethyl 2-Ureidobenzoates, or Isatoic Anhydrides
  作者：Michael Gütschow

  DOI：10.1021/jo9900634

  日期：1999.7.1

  The reaction of N-(mesyloxy)phthalimides with secondary amines was examined. Transformations are accomplished by one-pot reactions to optionally afford corresponding 2-ureidobenzamides, 2-ureidobenzoic acids, ethyl 2-ureidobenzoates, or isatoic anhydrides, respectively. The mechanism of the acid-catalyzed hydrolysis (or alcoholysis) of intermediate 2-ureidobenzamides to 2-ureidobenzoic acids (or esters)

  研究了 N-(甲磺酰氧基)邻苯二甲酰亚胺与仲胺的反应。转化通过一锅反应完成，以任选地分别提供相应的 2-脲基苯甲酰胺、2-脲基苯甲酸、2-脲基苯甲酸乙酯或靛红酸酐。讨论了中间体 2-脲基苯甲酰胺酸催化水解（或醇解）为 2-脲基苯甲酸（或酯）的机理。提出了涉及脲基部分作为内部酸催化剂的质子转移机制。中间体 2-脲基苯甲酸进一步转化为靛红酸酐。证明了利用所获得的 2-ureidobenzamides、2-ureidobenzoic 酸和 2-ureidobenzoate 来制备 3,1-benzoxazin-4-ones。