2-[(morpholinocarbonyl)amino]benzoic acid | 21282-65-5

• 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-[(morpholinocarbonyl)amino]benzoic acid
• 英文别名: 2-morpholinocarbonylaminobenzoic acid；2-(morpholine-4-carbonylamino)-benzoic acid；N-(morpholine-4-carbonyl)-anthranilic acid；N-(Morpholin-4-carbonyl)-anthranilsaeure；2-[(Morpholin-4-ylcarbonyl)amino]benzoic acid；2-(morpholine-4-carbonylamino)benzoic acid
• CAS: 21282-65-5
• 化学式: C₁₂H₁₄N₂O₄
• mdl: MFCD00591175
• 分子量: 250.254
• InChiKey: SKDLDQTXYBOMRY-UHFFFAOYSA-N

物化性质

• 沸点：
  525.8±50.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)
• 溶解度：
  >37.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(morpholinocarbonyl)amino]benzoic acid 在 盐酸 作用下， 反应 0.03h， 以68%的产率得到靛红酸酐
  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-morpholino-4H-3,1-benzoxazin-4-one 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 360.0h， 生成 2-[(morpholinocarbonyl)amino]benzoic acid
  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.
• Isatoic Anhydride. III. Reactions with Primary and Secondary Amines
  作者：Roger P. Staiger、E. C. Wagner

  DOI：10.1021/jo50016a024

  日期：1953.10
• 3,1-Benzothiazin-4-ones and 3,1-Benzoxazin-4-ones: Highly Different Activities in Chymotrypsin Inactivation
  作者：U. Neumann、M. Gutschow

  DOI：10.1006/bioo.1995.1006

  日期：1995.3

  3,1-Benzothiazin-4-ones are suIfur analogs of the potent serine protease inactivators of the 3, l-benzoxazin-4-one type, which acylate the serine residue within the active site of the enzymes. A series of 2-amino-3,1-benzothiazinones was synthesized, but these compounds showed only very little inhibitory activity toward chymotrypsin, a model serine protease. Detailed investigations revealed that benzothiazinones and benzoxazinones react with identical mechanisms, but benzothiazinones acylate chymotrypsin with much lower rate constants. Investigations of nonenzymatic hydrolysis showed the benzothiazinones to be intrinsically more stable than benzoxazinones. It was concluded from spectroscopic results, that benzoxazinones are highly activated due to the absence of ester-like resonance. 2-Benzoylamino-4H-3,1-benzoxazin-4-one was found to be a new, highly active chymotrypsin inactivator. In contrast, benzothiazinones were found to be resonance stabilized. The contribution of a resonance structure with an exocyclic oxanion to the overall structure of the benzothiazinones and its nonproductive binding to the active site explained their low reactivity toward chymotrypsin. (C) 1995 Academic Press, Inc.