2-isopropyl-N,N-dimethyl-imidazole-1-sulfonamide | 1416818-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-isopropyl-N,N-dimethyl-imidazole-1-sulfonamide
• 英文别名: 2-isopropyl-N,N-dimethyl-1H-imidazole-1-sulfonamide；N,N-dimethyl-2-propan-2-ylimidazole-1-sulfonamide
• CAS: 1416818-47-7
• 化学式: C₈H₁₅N₃O₂S
• 分子量: 217.292
• InChiKey: ZFCZWLJZIZHTNO-UHFFFAOYSA-N

物化性质

• 沸点：
  334.6±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-isopropyl-N,N-dimethyl-imidazole-1-sulfonamide 在 正丁基锂 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 3.5h， 生成 (1R,2R,3R,5S)-N-((2-isopropyl-1H-imidazol-5-yl)methyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine hydrochloride
  参考文献：
  名称：

  Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus

  摘要：

  We previously reported potent hit compound 4 inhibiting the wild-type influenza A virus A/HK/68 (H3N2) and A/M2-S31N mutant viruses A/WS/33 (H1N1), with its latter activity quite weak. To further increase its potency, a structure-activity relationship study of a series of imidazole-linked pinanamine derivatives was conducted by modifying the imidazole ring of this compound. Several compounds of this series inhibited the amantadine-sensitive virus at low micromolar concentrations. Among them, 33 was the most potent compound, which was identified as being active on an amantadine-sensitive virus through blocking of the viral M2 ion channel. Furthermore, 33 markedly inhibited the amantadine-resistant virus (IC50 = 3.4 mu M) and its activity increased by almost 24-fold compared to initial compound, with its action mechanism being not M2 channel mediated. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.013
• 作为产物：
  描述：

  2-异丙基咪唑 、 二甲胺基磺酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2-isopropyl-N,N-dimethyl-imidazole-1-sulfonamide
  参考文献：
  名称：

  设计，合成，结构-活性关系研究和X射线晶体学的3-取代的吲哚-2-二-5-羧酸酰胺衍生物作为PAK4抑制剂

  摘要：

  先前我们已经描述了将吲哚啉-2-一-5-羧酰胺确定为有效的PAK4抑制剂。这项研究通过对先导化合物2和3进行一些修饰，扩展了我们原始系列的构效关系。在生化和细胞分析中设计，合成和评估了一系列新型衍生物。该系列中的大多数显示出针对A549和HCT116细胞的纳摩尔生化活性和有效的抗增殖活性。代表性化合物10a表现出优异的酶抑制作用（PAK4 IC 50  = 25 nM）和细胞效价（A549 IC 50  = 0.58μM，HCT116 IC 50  = 0.095μM）。化合物的X射线结构获得与PAK4结合的10a。晶体学分析证实了分子模型的预测，并有助于改进SAR结果。另外，化合物10a显示出集中的多靶点激酶抑制作用，良好的计算药物相似性。化合物10a的进一步分析表明，它对人细胞色素P450的各种同工型均显示出弱的抑制活性。

  DOI：

  10.1016/j.ejmech.2018.05.051

文献信息

• LRRK2 INHIBITORS
  申请人：Bounaud Pierre-Yves

  公开号：US20140205537A1

  公开（公告）日：2014-07-24

  Provided herein are compounds that inhibit or partially inhibit the activity of leucine rich repeat kinases. Also provided herein are methods of treatment of CNS disorders comprising administration of inhibitors of leucine rich repeat kinases.

  本文提供了抑制或部分抑制富含亮氨酸重复激酶活性的化合物。本文还提供了治疗中枢神经系统疾病的方法，包括给予富含亮氨酸重复激酶抑制剂的治疗。
• [EN] ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS AND USES THEREOF<br/>[FR] AGONISTES DU RÉCEPTEUR D'ARYLE-HYDROCARBONE (AHR) ET LEURS UTILISATIONS
  申请人：IKENA ONCOLOGY INC

  公开号：WO2022133480A1

  公开（公告）日：2022-06-23

  The present invention provides AHR agonists, composites thereof, and methods of using the same.

  本发明提供AHR激动剂、其复合物以及使用方法。
• [EN] LRRK2 INHIBITORS<br/>[FR] INHIBITEURS DE LRRK2
  申请人：ZENOBIA THERAPEUTICS INC

  公开号：WO2012178015A3

  公开（公告）日：2013-05-10
• Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus
  作者：Jianghong Dong、Shengwei Chen、Runfeng Li、Wei Cui、Haiming Jiang、Yixia Ling、Zifeng Yang、Wenhui Hu

  DOI：10.1016/j.ejmech.2015.12.013

  日期：2016.1

  We previously reported potent hit compound 4 inhibiting the wild-type influenza A virus A/HK/68 (H3N2) and A/M2-S31N mutant viruses A/WS/33 (H1N1), with its latter activity quite weak. To further increase its potency, a structure-activity relationship study of a series of imidazole-linked pinanamine derivatives was conducted by modifying the imidazole ring of this compound. Several compounds of this series inhibited the amantadine-sensitive virus at low micromolar concentrations. Among them, 33 was the most potent compound, which was identified as being active on an amantadine-sensitive virus through blocking of the viral M2 ion channel. Furthermore, 33 markedly inhibited the amantadine-resistant virus (IC50 = 3.4 mu M) and its activity increased by almost 24-fold compared to initial compound, with its action mechanism being not M2 channel mediated. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, structure-activity relationships study and X-ray crystallography of 3-substituted-indolin-2-one-5-carboxamide derivatives as PAK4 inhibitors
  作者：Jing Guo、Fan Zhao、Wenbo Yin、Mingyue Zhu、Chenzhou Hao、Yu Pang、Tianxiao Wu、Jian Wang、Dongmei Zhao、Haitao Li、Maosheng Cheng

  DOI：10.1016/j.ejmech.2018.05.051

  日期：2018.7

  We have previously described the identification of indolin-2-one-5-carboxamides as potent PAK4 inhibitors. This study expands the structure-activity relationships on our original series by presenting several modifications in the lead compounds, 2 and 3. A series of novel derivatives was designed, synthesized, and evaluated in biochemical and cellular assay. Most of this series displayed nanomolar biochemical

  先前我们已经描述了将吲哚啉-2-一-5-羧酰胺确定为有效的PAK4抑制剂。这项研究通过对先导化合物2和3进行一些修饰，扩展了我们原始系列的构效关系。在生化和细胞分析中设计，合成和评估了一系列新型衍生物。该系列中的大多数显示出针对A549和HCT116细胞的纳摩尔生化活性和有效的抗增殖活性。代表性化合物10a表现出优异的酶抑制作用（PAK4 IC 50  = 25 nM）和细胞效价（A549 IC 50  = 0.58μM，HCT116 IC 50  = 0.095μM）。化合物的X射线结构获得与PAK4结合的10a。晶体学分析证实了分子模型的预测，并有助于改进SAR结果。另外，化合物10a显示出集中的多靶点激酶抑制作用，良好的计算药物相似性。化合物10a的进一步分析表明，它对人细胞色素P450的各种同工型均显示出弱的抑制活性。