N-cinnamoylanthranilic acid | 22780-31-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-cinnamoylanthranilic acid
• 英文别名: N-Cinnamoyl-anthranilsaeure；o-(Cinnamoylamino)-benzoesaeure；o-(Cinnamoylamino)-benzoic acid；2-Cinnamoylamino-benzoesaeure；2-(3-Phenylprop-2-enoylamino)benzoic acid
• CAS: 22780-31-0
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: GMEKUFJCKPYDAH-UHFFFAOYSA-N

物化性质

• 熔点：
  198 °C
• 沸点：
  528.5±50.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cinnamoylanthranilic acid 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-[[4-[(2-Chloroanilino)methyl]-5-phenyl-1,2-oxazolidin-3-ylidene]amino]benzoic acid
  参考文献：
  名称：

  Rani, Preeti; Srivastava; Kumar, Ashok, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1729 - 1733

  摘要：

  DOI：
• 作为产物：
  描述：

  肉桂酰氯 在 sodium hydroxide 作用下， 以 吡啶 为溶剂， 生成 N-cinnamoylanthranilic acid
  参考文献：
  名称：

  2-取代-4 H -3,1-苯并恶嗪-4-酮的合成

  摘要：

  邻氨基苯甲酸（1摩尔）在吡啶溶液中与苯甲酰氯（2摩尔）反应，以高收率得到2-苯基-4 H -3,1-苯并恶嗪-4-酮。与1摩尔。然而，得到了苯甲酰氯的苯并恶嗪酮和N-苯并氰基邻氨基苯甲酸的混合物。已经研究了反应的机理，并制备了各种2-取代的-4 H -3,1-苯并恶嗪-4-酮，并记录了它们的uv光谱。

  DOI：

  10.1039/j39680001593

文献信息

• Silica-bound benzoyl chloride mediated the solid-phase synthesis of 4<i>H</i>-3,1-benzoxazin-4-ones
  作者：Kurosh Rad-Moghadam、Somayeh Rouhi

  DOI：10.3762/bjoc.5.13

  日期：——

  The solid-phase synthesis of 4H-3,1-benzoxazin-4-ones was achieved using silica-bound benzoyl chloride (SBBC) as dehydrating agent in reaction with 2-acylaminobenzoic acids. The silica-grafted reagent (SBBC) was simply recovered after reaction and reused several times.

  使用硅胶结合的苯酰氯（SBBC）作为脱水剂，与2-酰胺基苯甲酸反应，实现了4H-3,1-苯并噁唑酮的固相合成。反应后，硅胶接枝试剂（SBBC）可以简单地回收并多次重复使用。
• A New Synthesis of 2-Substituted 4H-3,1-Benzoxazin-4-ones by Cyanuric Chloride Cyclodehydration of N-Benzoyl- and N-Acylanthranilic Acids
  作者：Mohammad S. Khajavi、Seyed M. Shariat

  DOI：10.3987/com-05-10364

  日期：——
• N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites
  作者：Arundhasa Chandrabalan、Martin J. McPhillie、Alyn H. Morice、Andrew N. Boa、Laura R. Sadofsky

  DOI：10.1016/j.ejmech.2019.02.074

  日期：2019.5

  The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators has not been fully elucidated. N-Cinnamoylanthranilic acid derivatives (CADs) contain structural elements from the TRPA1 modulators cinnamaldehyde and flufenamic acid, so it was hypothesized that specific modulators could be found amongst them and more could be learnt about modulation of TRPA1 with these compounds. A series of CADs was therefore screened for agonism and antagonism in HEK293 cells stably transfected with WT-human (h)TRPA1, or C621A, F909A or F944A mutant hTRPA1. Derivatives with electron-withdrawing and/or electron-donating substituents were found to possess different activities. CADs with inductive electron-withdrawing groups were agonists with desensitising effects, and CADs with electron-donating groups were either partial agonists or antagonists. Site-directed mutagenesis revealed that the CADs do not undergo conjugate addition reaction with TRPA1, and that F944 is a key residue involved in the non covalent modulation of TRPA1 by CADs, as well as many other structurally distinct non-reactive TRPA1 ligands already reported. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Kumar, Pradeep; Mukerjee, Arya K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 1, p. 24 - 26
  作者：Kumar, Pradeep、Mukerjee, Arya K.

  DOI：——

  日期：——
• Banerjee, Mrityunjay; Behera, Chinmoy C.; Pradhan, Guru C., South African Journal of Chemistry, 2009, vol. 62, p. 134 - 142
  作者：Banerjee, Mrityunjay、Behera, Chinmoy C.、Pradhan, Guru C.、Azam, M. Afzal、Sahu, Susant K.

  DOI：——

  日期：——