N-(4-nitrocinnamoyl)anthranilic acid | 550305-14-1

• 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-(4-nitrocinnamoyl)anthranilic acid
• 英文别名: 2-[3-(4-Nitrophenyl)prop-2-enoylamino]benzoic acid
• CAS: 550305-14-1
• 化学式: C₁₆H₁₂N₂O₅
• 分子量: 312.282
• InChiKey: UPNNOOAADGYKFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 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：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-nitrocinnamoyl)anthranilic acid 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以63%的产率得到2-((5-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-3-yl)amino)benzoic acid
  参考文献：
  名称：

  Banerjee, Mrityunjay; Behera, Chinmoy C.; Pradhan, Guru C., South African Journal of Chemistry, 2009, vol. 62, p. 134 - 142

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基肉桂酸 在 吡啶 、 光气 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.0h， 生成 N-(4-nitrocinnamoyl)anthranilic acid
  参考文献：
  名称：

  N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2019.02.074

文献信息

• METHODS OF USING CARBOXYLIC AMIDES AS ANTIMICROBIAL AGENTS
  申请人：Schroeder, JR. William

  公开号：US20110054034A1

  公开（公告）日：2011-03-03

  A method of treating a disease or condition in a warm blooded mammal which disease or condition is suspected to be associated with a microbial infection, comprising: administering an antimicrobial effective amount of a carboxylic acid amide, its isomers or salts thereof, to a subject who is suspected to be infected with a microbe. In one embodiment, the carboxylic acid amide is trans-3-(naphth-2-yl)-but-2-enoic acid-N-(2-carboxyphenyl)amide.
• US6127392A
  申请人：——

  公开号：US6127392A

  公开（公告）日：2000-10-03
• 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.
• 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：——