N,N′-(1,3-phenylene)bis(2-methylbenzamide)

• 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′-(1,3-phenylene)bis(2-methylbenzamide)
• 英文别名: 2-methyl-N-[3-[(2-methylbenzoyl)amino]phenyl]benzamide
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: BZCHGZDITBPKSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间苯二胺 、 邻甲基苯甲酰氯 在 三乙胺 作用下， 以 乙二醇二乙醚 为溶剂， 以45%的产率得到N-(3-氨基苯基)-2-甲基苯甲酰胺
  参考文献：
  名称：

  Identification and Electrophysiological Evaluation of 2-Methylbenzamide Derivatives as Na_v1.1 Modulators

  摘要：

  Voltage-gated sodium channels (Na-v) are crucial to the initiation and propagation of action potentials (APs) in electrically excitable cells, and during the past decades they have received considerable attention due to their therapeutic potential. Here, we report for the first time the synthesis and the electrophysiological evaluation of 16 ligands based on a 2-methylbenzamide scaffold that have been identified as Na(v)1.1 modulators. Among these compounds, N,N'-(1,3-phenylene)bis(2-methylbenzamide) (3a) has been selected and evaluated in ex-vivo experiments in order to estimate the activation impact of such a compound profile. It appears that 3a increases the Na(v)1.1 channel activity although its overall impact remains moderate. Altogether, our preliminary results provide new insights into the development of small molecule activators targeting specifically Na(v)1.1 channels to design potential drugs for treating CNS diseases.

  DOI：

  10.1021/acschemneuro.5b00147

文献信息

• PYRIDAZINONE DERIVATIVE
  申请人：Sumitomo Dainippon Pharma Co., Ltd.

  公开号：EP3828174A1

  公开（公告）日：2021-06-02

  Provided are: a pyridazinone derivative and/or a pharmaceutically acceptable salt thereof, which is useful as a therapeutic agent and/or a prophylactic agent for diseases in which Nav1.1 is involved and various central nervous system diseases; and a medicine containing the pyridazinone derivative and/or the pharmaceutically acceptable salt thereof as an active ingredient. A compound represented by formula (1) or a pharmaceutically acceptable salt thereof. [In the formula, M1 represents a saturated or partially unsaturated C4-12 carbocyclic group or the like; R1 and R2 independently represent a hydrogen atom or the like; M2 represents a group represented by formula (2a) or the like; X1a, X1b and X1c independently represent N or the like; X2, X3 and X4 independently represent CR3 or the like; A1 and A2 independently represent N or the like; and R3 represents a hydrogen atom or the like.]

  提供了：一种哒嗪酮衍生物和/或其药学上可接受的盐，可用作 Nav1.1 参与的疾病和各种中枢神经系统疾病的治疗剂和/或预防剂；以及一种含有该哒嗪酮衍生物和/或其药学上可接受的盐作为活性成分的药物。由式（1）代表的化合物或其药学上可接受的盐。 [式中，M1 代表饱和或部分不饱和的 C4-12 碳环基团或类似物；R1 和 R2 独立地代表氢原子或类似物；M2 代表式 (2a) 所代表的基团或类似物；X1a、X1b 和 X1c 独立地代表 N 或类似物；X2、X3 和 X4 独立地代表 CR3 或类似物；A1 和 A2 独立地代表 N 或类似物；以及 R3 代表氢原子或类似物。］
• US4092431A
  申请人：——

  公开号：US4092431A

  公开（公告）日：1978-05-30
• Identification and Electrophysiological Evaluation of 2-Methylbenzamide Derivatives as Na_v1.1 Modulators
  作者：François Crestey、Kristen Frederiksen、Henrik S. Jensen、Kim Dekermendjian、Peter H. Larsen、Jesper F. Bastlund、Dunguo Lu、Henry Liu、Charles R. Yang、Morten Grunnet、Niels Svenstrup

  DOI：10.1021/acschemneuro.5b00147

  日期：2015.8.19

  Voltage-gated sodium channels (Na-v) are crucial to the initiation and propagation of action potentials (APs) in electrically excitable cells, and during the past decades they have received considerable attention due to their therapeutic potential. Here, we report for the first time the synthesis and the electrophysiological evaluation of 16 ligands based on a 2-methylbenzamide scaffold that have been identified as Na(v)1.1 modulators. Among these compounds, N,N'-(1,3-phenylene)bis(2-methylbenzamide) (3a) has been selected and evaluated in ex-vivo experiments in order to estimate the activation impact of such a compound profile. It appears that 3a increases the Na(v)1.1 channel activity although its overall impact remains moderate. Altogether, our preliminary results provide new insights into the development of small molecule activators targeting specifically Na(v)1.1 channels to design potential drugs for treating CNS diseases.