1,4-二甲基-5-硝基吲哚 | 143797-99-3

• 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
• 中文名称: 1,4-二甲基-5-硝基吲哚
• 英文名称: 1,4-dimethyl-5-nitroindole
• 英文别名: 1H-Indole, 1,4-dimethyl-5-nitro-
• CAS: 143797-99-3
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: VUJKPSOEFJZRLD-UHFFFAOYSA-N

物化性质

• 沸点：
  345.9±22.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-二甲基-5-硝基吲哚 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、551.58 kPa 条件下， 反应 52.17h， 生成 6-methyl 1,2,3,6-tetrahydropyrrolo<3,2-e>indole methanesulfonate
  参考文献：
  名称：

  5-Methyl-1-(3-pyridylcarbamoyl)-1,2,3,5-tetrahydropyrrolo[2,3-f]indole: A Novel 5-HT2C/5-HT2B Receptor Antagonist with Improved Affinity, Selectivity, and Oral Activity

  摘要：

  The preparation of a series of conformationally restricted analogues of indolylurea 1, namely tetrahydropyrroloindoles and tetrahydropyrroloquinolines, is described. The binding affinities of these compounds at 5-HT2A, 5-HT2B, and 5-HT2C receptors were determined. Of these compounds, the 1,2,3,5-tetrahydropyrrolo[2,3-f]indole derivative, compound 11, was found to have high affinity for the 5-HT2C (pK(I) 8.0) and 5-HT2B receptors (pA(2) 8.5), with excellent selectivity over the 5-HT2A and various other receptors (pK(I) <6). 11 is also considerably more active than 1 in both an in vitro functional model, 5-HT-stimulated phosphoinositol hydrolysis (pK(B) 8.8), and an in vivo functional model, mCPP-induced hypolocomotion (ID50 5.5 mg/kg po). 11 should therefore be of significant utility as a pharmacological tool to delineate the functional significance of blockade of 5-HT2B and 5-HT2C receptors.

  DOI：

  10.1021/jm00014a004
• 作为产物：
  描述：

  1-甲基-5-硝基-1H-吲哚 、 甲基溴化镁 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 1,4-二甲基-5-硝基吲哚
  参考文献：
  名称：

  5-Methyl-1-(3-pyridylcarbamoyl)-1,2,3,5-tetrahydropyrrolo[2,3-f]indole: A Novel 5-HT2C/5-HT2B Receptor Antagonist with Improved Affinity, Selectivity, and Oral Activity

  摘要：

  The preparation of a series of conformationally restricted analogues of indolylurea 1, namely tetrahydropyrroloindoles and tetrahydropyrroloquinolines, is described. The binding affinities of these compounds at 5-HT2A, 5-HT2B, and 5-HT2C receptors were determined. Of these compounds, the 1,2,3,5-tetrahydropyrrolo[2,3-f]indole derivative, compound 11, was found to have high affinity for the 5-HT2C (pK(I) 8.0) and 5-HT2B receptors (pA(2) 8.5), with excellent selectivity over the 5-HT2A and various other receptors (pK(I) <6). 11 is also considerably more active than 1 in both an in vitro functional model, 5-HT-stimulated phosphoinositol hydrolysis (pK(B) 8.8), and an in vivo functional model, mCPP-induced hypolocomotion (ID50 5.5 mg/kg po). 11 should therefore be of significant utility as a pharmacological tool to delineate the functional significance of blockade of 5-HT2B and 5-HT2C receptors.

  DOI：

  10.1021/jm00014a004

文献信息

• 三环类化合物、其药物组合物及其应用
  申请人：[en]CHOLESGEN (SHANGHAI) CO.LTD.;[zh]珂阑（上海）医药科技有限公司

  公开号：WO2024140595A1

  公开（公告）日：2024-07-04

  本发明公开了一种三环类化合物、其药物组合物及其应用。具体地，本发明公开了一种如式(I)所示的化合物或其药学上可接受的盐。本发明所述的如式(I)所示的化合物或其药学上可接受的盐具有以下一个或多个优点：具有良好的SMO抑制性；表现出良好的Hh信号通路抑制能力；具有良好的肝微粒体代谢稳定性。
• BARTOLI, GIUSEPPE;BOSCO, MARCELLA;CARETTI, DANIELE;DALPOZZO, RENATO;TODES+, J. ORG. CHEM., 52,(1987) N 19, 4381-4384
  作者：BARTOLI, GIUSEPPE、BOSCO, MARCELLA、CARETTI, DANIELE、DALPOZZO, RENATO、TODES+

  DOI：——

  日期：——
• INDOLE UREAS AS 5 HT RECEPTOR ANTAGONIST
  申请人：Beecham Group p.l.c.

  公开号：EP0550507A1

  公开（公告）日：1993-07-14
• US5328922A
  申请人：——

  公开号：US5328922A

  公开（公告）日：1994-07-12
• [EN] INDOLE UREAS AS 5 HT RECEPTOR ANTAGONIST
  申请人：——

  公开号：WO1992005170A1

  公开（公告）日：1992-04-02

  [EN] Indole ureas, pharmaceutical compositions containing them and processes for their preparation.
  [FR] Urées d'indole, compositions pharmaceutiques les contenant et leurs procédés de préparation.