4-nitro-5-(piperidin-1-yl)benzene-1,2-diamine | 1319671-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-nitro-5-(piperidin-1-yl)benzene-1,2-diamine
• 英文别名: 4-Nitro-5-piperidin-1-ylbenzene-1,2-diamine；4-nitro-5-piperidin-1-ylbenzene-1,2-diamine
• CAS: 1319671-80-1
• 化学式: C₁₁H₁₆N₄O₂
• 分子量: 236.274
• InChiKey: YQYACYYVZHSHJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-nitro-5-(piperidin-1-yl)benzene-1,2-diamine 在 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 7.0h， 生成 2-[(3,4-dimethoxypyridin-2-yl)methylthio]-6-nitro-5-(piperidin-1-yl)-1H-benzimidazole
  参考文献：
  名称：

  A reverse method for diversity introduction of benzimidazole to synthesize H+/K+-ATP enzyme inhibitors

  摘要：

  A series of 2-[(2-pyridylmethyl)sulfinyl]benzimidazole derivatives were synthesized via a solution phase synthetic route using a reversal method of diversity introduction. Using this synthetic strategy, we obtained two key intermediates (4-A and 4-B) simultaneously, which allows us to introduce diversity points onto the benzimidazole part of the final product under reliable reaction conditions to identify potent H+/K+-ATP enzyme inhibitors. Compound 141 (IC50 = 1.6 x 10 (5) M) was comparable with H+/K+-ATP enzyme inhibitor in vitro. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.080
• 作为产物：
  描述：

  2,4-二硝基-5-氟苯胺 在 sodium hydrogensulfide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 2-nitro-5-(piperidin-1-yl)benzene-1,4-diamine 、 4-nitro-5-(piperidin-1-yl)benzene-1,2-diamine
  参考文献：
  名称：

  A reverse method for diversity introduction of benzimidazole to synthesize H+/K+-ATP enzyme inhibitors

  摘要：

  A series of 2-[(2-pyridylmethyl)sulfinyl]benzimidazole derivatives were synthesized via a solution phase synthetic route using a reversal method of diversity introduction. Using this synthetic strategy, we obtained two key intermediates (4-A and 4-B) simultaneously, which allows us to introduce diversity points onto the benzimidazole part of the final product under reliable reaction conditions to identify potent H+/K+-ATP enzyme inhibitors. Compound 141 (IC50 = 1.6 x 10 (5) M) was comparable with H+/K+-ATP enzyme inhibitor in vitro. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.080

文献信息

• [EN] BENZIMIDAZOLES AND PHARMACEUTICAL COMPOSITIONS THEREOF<br/>[FR] BENZIMIDAZOLES ET COMPOSITIONS PHARMACEUTIQUES DE CEUX-CI
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2008130669A1

  公开（公告）日：2008-10-30

  [EN] The present invention relates to novel benzimidazole derivatives and pharmaceutically acceptable salts thereof. Another aspect of the invention relates to methods of treating a patient infected by Mycobacterium tuberculosis or Francisella tulerensis by administering to the patient a benzimidazole derivative or a pharmaceutically acceptable salt thereof.
  [FR] L'invention concerne de nouveaux dérivés du benzimidazole et des sels pharmaceutiquement acceptables de ceux-ci. Un autre aspect de l'invention concerne des procédés de traitement d'un patient infecté par Mycobacterium tuberculosis ou Francisella tulerensis par l'administration au patient d'un dérivé du benzimidazole ou d'un sel pharmaceutiquement acceptable de celui-ci.
• A reverse method for diversity introduction of benzimidazole to synthesize H+/K+-ATP enzyme inhibitors
  作者：Yu Yan、Zijie Liu、Jianjun Zhang、Ruiming Xu、Xiao Hu、Gang Liu

  DOI：10.1016/j.bmcl.2011.05.080

  日期：2011.7

  A series of 2-[(2-pyridylmethyl)sulfinyl]benzimidazole derivatives were synthesized via a solution phase synthetic route using a reversal method of diversity introduction. Using this synthetic strategy, we obtained two key intermediates (4-A and 4-B) simultaneously, which allows us to introduce diversity points onto the benzimidazole part of the final product under reliable reaction conditions to identify potent H+/K+-ATP enzyme inhibitors. Compound 141 (IC50 = 1.6 x 10 (5) M) was comparable with H+/K+-ATP enzyme inhibitor in vitro. (C) 2011 Elsevier Ltd. All rights reserved.