3-Aminomethyl-1,2-dimethylindol | 60011-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-Aminomethyl-1,2-dimethylindol
• 英文别名: C-(1,2-dimethyl-indol-3-yl)-methylamine；(1,2-dimethyl-1H-indol-3-yl)methanamine；(1,2-dimethylindol-3-yl)methanamine
• CAS: 60011-68-9
• 化学式: C₁₁H₁₄N₂
• mdl: MFCD06213481
• 分子量: 174.246
• InChiKey: ZGVHYGYSHCIXSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  31
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基肉桂酸 、 3-Aminomethyl-1,2-dimethylindol 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (E)-N-((1,2-dimethyl-1H-indol-3-yl)methyl)-3-(3,4,5-trimethoxyphenyl)acrylamide
  参考文献：
  名称：

  Lead Optimization Studies of Cinnamic Amide EP2 Antagonists

  摘要：

  Prostanoid receptor EP2 can play a proinflammatory role, exacerbating disease pathology in a variety of central nervous system and peripheral diseases. A highly selective EP2 antagonist could be useful as a drug to mitigate the inflammatory consequences of EP2 activation. We recently identified a cinnamic amide class of EP2 antagonists. The lead compound in this class (5d) displays anti-inflammatory and neuroprotective actions. However, this compound exhibited moderate selectivity to EP2 over the DP1 prostanoid receptor (similar to 10-fold) and low aqueous solubility. We now report compounds that display up to 180-fold selectivity against DP1 and up to 9-fold higher aqueous solubility than our previous lead. The newly developed compounds also display higher selectivity against EP4 and IP receptors and a comparable plasma pharmacokinetics. Thus, these compounds are useful for proof of concept studies in a variety of models where EP2 activation is playing a deleterious role.

  DOI：

  10.1021/jm5000672
• 作为产物：
  描述：

  3-(azidomethyl)-1,2-dimethyl-1H-indole 生成 3-Aminomethyl-1,2-dimethylindol
  参考文献：
  名称：

  MAKISUMI Y.; TAKADA S., CHEM. AND PHARM. BULL. , 1976, 24, NO 4, 770-777

  摘要：

  DOI：

文献信息

• Methyl-triflate-mediated dearylmethylation of <i>N</i>-(arylmethyl)carboxamides <i>via</i> the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature
  作者：Hui Peng、Jinhui Ma、Wenkun Luo、Guangwen Zhang、Biaolin Yin

  DOI：10.1039/c9gc00176j

  日期：——

  Dearylmethylation of N-(arylmethyl)carboxamides was achieved under metal-free conditions in an aqueous medium induced by electrophilic dearomatization/rearomatization.

  在无金属条件下，在水介质中通过亲电脱芳香化/重芳香化实现了N-(芳甲基)羧酰胺的去芳甲基化。
• HDAC INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
  申请人：Kozikowski Alan

  公开号：US20140128408A1

  公开（公告）日：2014-05-08

  Histone deacetylases inhibitors (HDACIs) and compositions containing the same are disclosed. Methods of treating diseases and conditions wherein inhibition of HDAC provides a benefit, like a cancer, a neurodegenerative disorder, a peripheral neuropathy, a neurological disease, traumatic brain injury, stroke, hypertension, malaria, an autoimmune disease, autism, autism spectrum disorders, and inflammation, also are disclosed.

  本发明公开了组蛋白去乙酰化酶抑制剂（HDACIs）及其组成物。公开了治疗疾病和状况的方法，其中抑制HDAC提供了益处，如癌症、神经退行性疾病、周围神经病变、神经疾病、创伤性脑损伤、中风、高血压、疟疾、自身免疫疾病、自闭症、自闭症谱系障碍和炎症。
• N-HYDROXYBENZAMIDE DERIVATIVES AS HDAC INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
  申请人：The Board of Trustees of the University of Illinois

  公开号：EP2670733B1

  公开（公告）日：2019-04-10
• Lead Optimization Studies of Cinnamic Amide EP2 Antagonists
  作者：Thota Ganesh、Jianxiong Jiang、Myung-Soon Yang、Ray Dingledine

  DOI：10.1021/jm5000672

  日期：2014.5.22

  Prostanoid receptor EP2 can play a proinflammatory role, exacerbating disease pathology in a variety of central nervous system and peripheral diseases. A highly selective EP2 antagonist could be useful as a drug to mitigate the inflammatory consequences of EP2 activation. We recently identified a cinnamic amide class of EP2 antagonists. The lead compound in this class (5d) displays anti-inflammatory and neuroprotective actions. However, this compound exhibited moderate selectivity to EP2 over the DP1 prostanoid receptor (similar to 10-fold) and low aqueous solubility. We now report compounds that display up to 180-fold selectivity against DP1 and up to 9-fold higher aqueous solubility than our previous lead. The newly developed compounds also display higher selectivity against EP4 and IP receptors and a comparable plasma pharmacokinetics. Thus, these compounds are useful for proof of concept studies in a variety of models where EP2 activation is playing a deleterious role.
• MAKISUMI Y.; TAKADA S., CHEM. AND PHARM. BULL. <CPBT-AL>, 1976, 24, NO 4, 770-777
  作者：MAKISUMI Y.、 TAKADA S.

  DOI：——

  日期：——