2-(1-methyl-2-(phenylsulfonyl)-1H-imidazol-5-yl)phenol | 1236073-89-4

• 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-(1-methyl-2-(phenylsulfonyl)-1H-imidazol-5-yl)phenol
• 英文别名: 2-[2-(Benzenesulfonyl)-3-methylimidazol-4-yl]phenol
• CAS: 1236073-89-4
• 化学式: C₁₆H₁₄N₂O₃S
• 分子量: 314.365
• InChiKey: ZBUVODURGKCABV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-methyl-2-(phenylsulfonyl)-1H-imidazol-5-yl)phenol 在 n-甲基-硫代乙酰胺 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.0h， 以70 mg的产率得到2-(2-mercapto-1-methyl-1H-imidazol-5-yl)phenol
  参考文献：
  名称：

  新規ピリミジン誘導体及びこれらを含有する抗菌剤

  摘要：

  这个句子的翻译为：具有比叶酸还原酶抑制活性更高的新化合物，或其盐，可以扩大对抗耐药菌引起的感染症的药物治疗选择范围，同时提供包含该新化合物或其盐的抗菌剂，提供更有效的叶酸还原酶抑制剂。【解决方案】提供具有下述式（I）所示的2,4-二氨基嘌呤骨架的化合物，或其盐，以及以该化合物或其盐为有效成分的抗菌剂。【化1】【无图】

  公开号：

  JP2018154587A
• 作为产物：
  描述：

  2-溴苯酚 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 水 为溶剂， 反应 2.0h， 生成 2-(1-methyl-2-(phenylsulfonyl)-1H-imidazol-5-yl)phenol
  参考文献：
  名称：

  New 5-Aryl-1H-imidazoles Display in Vitro Antitumor Activity against Apoptosis-Resistant Cancer Models, Including Melanomas, through Mitochondrial Targeting

  摘要：

  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.

  DOI：

  10.1021/jm400287v

文献信息

• Synthesis and biological evaluation of novel imidazole-containing macrocycles
  作者：Prosper Nshimyumukiza、Emilie Van Den Berge、Bruno Delest、Tatjana Mijatovic、Robert Kiss、Jacqueline Marchand-Brynaert、Raphaël Robiette

  DOI：10.1016/j.tet.2010.04.070

  日期：2010.6

  A new family of compounds made of a 5-aryl-1H-imidazole motif included in a macrocycle has been designed and synthesized. The synthesis of the imidazole core makes use of our previously developed method for the regioselective preparation of 1,2,5-trisubstituted imidazoles while the construction of the macrocycle is based on a three steps sequence: SNAr, Suzuki coupling, and RCM reaction. Biological evaluation of synthesized imidazole-containing macrocycles revealed that they display actual binding activity toward A(3) adenosine (h) receptor, dopamine D-1 (h) receptor, chloride channel (GABA-gated), and choline transporter (h) CHT1. (C) 2010 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.
• 新規ピリミジン誘導体及びこれらを含有する抗菌剤
  申请人：Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社

  公开号：JP2018154587A

  公开（公告）日：2018-10-04

  【課題】より効果の高いジヒドロ葉酸還元酵素阻害活性を有し、耐性菌を起因菌とする感染症に対する薬物治療の選択肢の幅を広げることができる新規化合物、またはその塩、及び前記新規化合物、またはその塩を含有する抗菌剤を提供すること、より効果の高いジヒドロ葉酸還元酵素阻害剤を提供することにある。【解決手段】下記式（Ｉ）で表される、２、４−ジアミノピリミジン骨格を有する化合物、またはその塩、前記化合物、またはその塩を有効成分とする抗菌剤を提供する。 【化１】【選択図】なし

  这个句子的翻译为：具有比叶酸还原酶抑制活性更高的新化合物，或其盐，可以扩大对抗耐药菌引起的感染症的药物治疗选择范围，同时提供包含该新化合物或其盐的抗菌剂，提供更有效的叶酸还原酶抑制剂。【解决方案】提供具有下述式（I）所示的2,4-二氨基嘌呤骨架的化合物，或其盐，以及以该化合物或其盐为有效成分的抗菌剂。【化1】【无图】