1-[1-(2-amino-ethyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one | 312501-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-[1-(2-amino-ethyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one
• 英文别名: 1-[1-(2-aminoethyl)-4-piperidinyl]-1,3-dihydro-2(2H)-benzimidazolone；3-[1-(2-aminoethyl)piperidin-4-yl]-1H-benzimidazol-2-one
• CAS: 312501-24-9
• 化学式: C₁₄H₂₀N₄O
• 分子量: 260.339
• InChiKey: AWCASWHSVVEIBD-UHFFFAOYSA-N

物化性质

• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氟吲哚-2-甲酸 、 1-[1-(2-amino-ethyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one 在 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 生成 5-氟-2-吲哚基脱氯卤培米特
  参考文献：
  名称：

  Optimization of Halopemide for Phospholipase D2 inhibition

  摘要：

  Halopemide, which was identified by HTS to inhibit phospholipase D2 (PLD2), provided the basis for an exploratory effort to identify potent inhibitors of PLD2 for use as inflammatory mediators. Parallel synthesis and purification were utilized to rapidly identify orally available amide analogs derived from indole 2-carboxylic acids with superior potency versus PLD2. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.059
• 作为产物：
  描述：

  4-(1,3-dihydro-2(2H)-oxo-1-benzimidazolyl)-1-{2-[(1,1-di-methylethoxycarbonyl)amino]ethyl}piperidine 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-[1-(2-amino-ethyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one
  参考文献：
  名称：

  Optimization of Halopemide for Phospholipase D2 inhibition

  摘要：

  Halopemide, which was identified by HTS to inhibit phospholipase D2 (PLD2), provided the basis for an exploratory effort to identify potent inhibitors of PLD2 for use as inflammatory mediators. Parallel synthesis and purification were utilized to rapidly identify orally available amide analogs derived from indole 2-carboxylic acids with superior potency versus PLD2. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.059

文献信息

• Arylalkane, arylalkene and aryl azaalkane, medicaments containing said compounds and method for the production thereof
  申请人：Boehringer Ingelheim Pharma GmbH & Co. KG

  公开号：US07230001B1

  公开（公告）日：2007-06-12

  The present invention relates to compounds of general formula R—Z1—Z2—Z3—R1,   (I) wherein R, R1 and Z1 to Z3 are defined as in claim 1, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable pharmacological properties, particularly CGRP-antagonistic properties, pharmaceutical compositions containing these compounds, their use and processes for preparing them.

  本发明涉及一般式 R—Z1—Z2—Z3—R1，  (I) 其中 R、R1和Z1至Z3如权利要求1中所定义，其互变异构体、对映异构体、立体异构体、它们的混合物及其盐，特别是其与无机或有机酸或碱的生理上可接受的盐，具有有价值的药理特性，特别是CGRP拮抗特性，含有这些化合物的药物组合物，它们的用途和制备它们的方法。
• Design and synthesis of isoform-selective phospholipase D (PLD) inhibitors. Part I: Impact of alternative halogenated privileged structures for PLD1 specificity
  作者：Jana A. Lewis、Sarah A. Scott、Robert Lavieri、Jason R. Buck、Paige E. Selvy、Sydney L. Stoops、Michelle D. Armstrong、H. Alex Brown、Craig W. Lindsley

  DOI：10.1016/j.bmcl.2009.02.057

  日期：2009.4

  This Letter describes the synthesis and structure-activity-relationships (SAR) of isoform-selective PLD inhibitors. By virtue of the installation of alternative halogenated piperidinyl benzimidazolone privileged structures, in combination with a key ( S)-methyl group, novel PLD inhibitors with low nM potency and unprecedented levels of PLD1 isoform selectivity (similar to 1700-fold) over PLD2 were developed. (C) 2009 Elsevier Ltd. All rights reserved.
• MODULATION OF PHOSPHOLIPASE D FOR THE TREATMENT OF NEURODEGENERATIVE DISORDERS
  申请人：DiPaolo Gilbert

  公开号：US20120178719A1

  公开（公告）日：2012-07-12

  The present invention relates to methods of treating neurodegenerative diseases comprising administering, to a subject in need of such treatment, one or more agent that inhibits or reduces the action, including the catalytic activity, of an enzyme of the phospholipase D family, such as phospholipase D1 and/or phospholipase D2. The present invention also relates to cell-based assays which may be used to identify agents that inhibit or reduce the activity of enzymes of the phospholipase D family and that may be used in the treatment of neurodegenerative diseases.
• Modulation of Phospholipase D for the Treatment of the Acute and Chronic Effects of Ethanol
  申请人：DiPaolo Gilbert

  公开号：US20120302604A1

  公开（公告）日：2012-11-29

  The present invention relates to methods of decreasing the negative effects of alcohol on behavior as well as inhibiting the toxic effects of alcohol, comprising administering, to a subject, an effective amount of an inhibitor of phospholipase D.
• US7230001B1
  申请人：——

  公开号：US7230001B1

  公开（公告）日：2007-06-12