3-amino-5-fluoro-2-methoxybenzoic acid | 151793-23-6

• 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: 3-amino-5-fluoro-2-methoxybenzoic acid
• CAS: 151793-23-6
• 化学式: C₈H₈FNO₃
• 分子量: 185.155
• InChiKey: ZETUEBGPEOOIMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-5-fluoro-2-methoxybenzoic acid 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-Amino-N-(2-diethylamino-ethyl)-5-fluoro-2-methoxy-benzamide
  参考文献：
  名称：

  Synthesis and preliminary data on new selective and potent gastric prokinetic substituted benzamides

  摘要：

  A series of amino-halogen-N-[2-aminoethyl] benzamides was synthesized and evaluated for enhancing gastric emptying. Compared to metoclopramide, domperidone and bromopride, a number of compounds were shown to be more active in enhancing gastric motility (rat stomach emptying), devoid of dopaminergic D2-receptor antagonism (rat apomorphine test) and to be less toxic.

  DOI：

  10.1016/0223-5234(93)90129-3
• 作为产物：
  描述：

  5-氟-2-甲氧基苯甲酸甲酯 在 Ni-Raney sodium hydroxide 、 硫酸 、 氢气 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 1.17h， 生成 3-amino-5-fluoro-2-methoxybenzoic acid
  参考文献：
  名称：

  Synthesis and preliminary data on new selective and potent gastric prokinetic substituted benzamides

  摘要：

  A series of amino-halogen-N-[2-aminoethyl] benzamides was synthesized and evaluated for enhancing gastric emptying. Compared to metoclopramide, domperidone and bromopride, a number of compounds were shown to be more active in enhancing gastric motility (rat stomach emptying), devoid of dopaminergic D2-receptor antagonism (rat apomorphine test) and to be less toxic.

  DOI：

  10.1016/0223-5234(93)90129-3

文献信息

• Novel TYK2 Inhibitors with an <i>N</i>-(Methyl-<i>d</i>₃)pyridazine-3-carboxamide Skeleton for the Treatment of Autoimmune Diseases
  作者：Fei Liu、Bin Wang、Yanlong Liu、Wei Shi、Xujing Tang、Xiaojin Wang、Zhongyuan Hu、Ying Zhang、Yahui Guo、Xiayun Chang、Xiangyi He、Hongjiang Xu、Ying He

  DOI：10.1021/acsmedchemlett.2c00334

  日期：2022.11.10

  than the positive control deucravacitinib. In addition to JAK isoform selectivity, compound 30 exhibited good in vivo and in vitro pharmacokinetic properties. Furthermore, compound 30 was orally highly effective in both IL-23-driven acanthosis and anti-CD40-induced colitis models. Together, these findings support compound 30 as a promising candidate for therapeutic applications in autoimmune diseases

  酪氨酸激酶 2 (TYK2) 介导白细胞介素 23 (IL-23)、IL-12 和 I 型干扰素 (IFN) 驱动的信号反应，这些信号反应在自身免疫性疾病中至关重要。在此，设计、合成并评估了一系列具有N- (甲基-d 3 )哒嗪-3-甲酰胺骨架、与 TYK2 假激酶结构域结合的新型衍生物。其中，化合物30比阳性对照deucravacitinib表现出更优异的STAT3磷酸化抑制效力。除了 JAK 同工型选择性外，化合物30还表现出良好的体内和体外药代动力学特性。此外，口服化合物30在IL-23驱动的棘皮症和抗CD40诱导的结肠炎模型中均非常有效。总之，这些发现支持化合物30作为自身免疫性疾病治疗应用的有希望的候选者。
• Synthesis and preliminary data on new selective and potent gastric prokinetic substituted benzamides
  作者：L Del Corona、G Signorelli、A Pinzetta、G Coppi

  DOI：10.1016/0223-5234(93)90129-3

  日期：1993.1

  A series of amino-halogen-N-[2-aminoethyl] benzamides was synthesized and evaluated for enhancing gastric emptying. Compared to metoclopramide, domperidone and bromopride, a number of compounds were shown to be more active in enhancing gastric motility (rat stomach emptying), devoid of dopaminergic D2-receptor antagonism (rat apomorphine test) and to be less toxic.