2-benzenesulfonyl-1-methyl-1H-imidazole | 465617-04-3

• 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: 2-benzenesulfonyl-1-methyl-1H-imidazole
• 英文别名: 2-(Benzenesulfonyl)-1-methylimidazole
• CAS: 465617-04-3
• 化学式: C₁₀H₁₀N₂O₂S
• 分子量: 222.268
• InChiKey: YMGMBOOGZVIHOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  417.8±28.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-哌啶丙醇 、 2-benzenesulfonyl-1-methyl-1H-imidazole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.5h， 生成 1-[3-(1-methyl-1H-imidazol-2-yloxy)propyl]piperidine
  参考文献：
  名称：

  Scalable synthesis of imidazole derivatives

  摘要：

  咪唑衍生物，含有它们的组合物，制备它们的方法，包括选择性区域放大合成方法，以及使用它们的方法。

  公开号：

  US20050250948A1
• 作为产物：
  描述：

  1-methyl-2-phenylsulfanyl-1H-imidazole 在 m-chloroperoxybenzoic acid 作用下， 以 乙醚 为溶剂， 生成 2-benzenesulfonyl-1-methyl-1H-imidazole
  参考文献：
  名称：

  Heterocyclic compounds

  摘要：

  药用的杂环化合物，含有它们的组合物以及使用它们的方法，例如，作为组胺H3受体介导剂。

  公开号：

  US20020198237A1

文献信息

• SCALABLE SYNTHESIS OF IMIDAZOLE DERIVATIVES
  申请人：JONES Todd K.

  公开号：US20090143591A1

  公开（公告）日：2009-06-04

  Imidazole derivatives, compositions containing them, methods of preparing them, including regioselective scale-up synthetic methods, and methods of using them.

  咪唑衍生物、含有它们的组合物、制备它们的方法（包括区域选择性放大合成方法）以及使用它们的方法。
• Novel imidazole-based histamine H3 antagonists
  作者：Jill A. Jablonowski、Kiev S. Ly、Michael Bogenstaetter、Curt A. Dvorak、Jamin D. Boggs、Lisa K. Dvorak、Brian Lord、Kirsten L. Miller、Curt Mazur、Sandy J. Wilson、Timothy W. Lovenberg、Nicholas I. Carruthers

  DOI：10.1016/j.bmcl.2008.11.114

  日期：2009.2

  A novel series of imidazole containing histamine H-3 receptor ligands were investigated and found to be potent functional antagonists. After improving the stability of these molecules towards liver microsomes, these compounds were found to have no appreciable affinity for CYP P450s. Subsequent in vivo experiments showed significant brain uptake of (4-chloro-phenyl)-[2-(1-isopropyl-piperidin-4-ylmethoxy)-3-methyl-3H-imidazol-4-yl]-methanone 22. (C) 2008 Elsevier Ltd. All rights reserved.
• New 5-Aryl-1<i>H</i>-imidazoles Display in Vitro Antitumor Activity against Apoptosis-Resistant Cancer Models, Including Melanomas, through Mitochondrial Targeting
  作者：Véronique Mathieu、Emilie Van Den Berge、Justine Ceusters、Tomasz Konopka、Antonin Cops、Céline Bruyère、Christine Pirker、Walter Berger、Tran Trieu-Van、Didier Serteyn、Robert Kiss、Raphaël Robiette

  DOI：10.1021/jm400287v

  日期：2013.9.12

  We designed and synthesized 48 aryl-1H-imidazole derivatives and investigated their in vitro growth inhibitory activity in cancer cell lines known to present various levels of resistance to proapoptotic stimuli. The IC50 in vitro growth inhibitory concentration of these compounds ranged from >100 mu M to single digit mu M. Among the most active compounds, 2i displayed similar in vitro growth inhibition in cancer cells independent of the cells' levels of resistance to proapoptotic stimuli and was found to be cytostatic in melanoma cell lines. Compound 2i was then tested by the National Cancer Institute Human Tumor Cell Line Anti-Cancer Drug Screen, and the NCI COMPARE algorithm did not reveal any correlation between its growth inhibition profiles with the NCI database compound profiles. The use of transcriptomically characterized melanoma models then enabled us to highlight mitochondrial targeting by 2i. This hypothesis was further confirmed by reactive oxygen production measurement and oxygen consumption analysis.
• Parallel synthesis and evaluation of N-(1-phenylethyl)-5-phenyl-imidazole-2-amines as Na+/K+ ATPase inhibitors
  作者：Benjamin E. Blass、C.T. Huang、Richard M. Kawamoto、Min Li、Song Liu、David E. Portlock、William M. Rennells、Melanie Simmons

  DOI：10.1016/s0960-894x(00)00296-1

  日期：2000.7

  A series of N-(1-phenylethyl)-5-phenyl-imidazole-2-amines was prepared using solution-phase, parallel synthesis and evaluated for Na+/K+ ATPase inhibition. (C) 2000 Elsevier Science Ltd. All rights reserved.
• IMIDAZOLYL DERIVATIVES USEFUL AS HISTAMINE H3 RECEPTOR LIGANDS
  申请人：Ortho-McNeil-Janssen Pharmaceuticals, Inc.

  公开号：EP1373218B9

  公开（公告）日：2008-12-03