吗丁啉杂质13 | 87120-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 吗丁啉杂质13
• 英文名称: 1-ethoxycarbonyl-4-(2-aminophenyl)aminopiperidine
• 英文别名: ethyl 4-((2-aminophenyl)amino)piperidine-1-carboxylate；4-(2-amino-phenylamino)-piperidine-1-carboxylic acid ethyl ester；Ethyl 4-(2-aminoanilino)piperidine-1-carboxylate
• CAS: 87120-77-2
• 化学式: C₁₄H₂₁N₃O₂
• 分子量: 263.34
• InChiKey: CHFSPWXIDIDPTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吗丁啉杂质13 在 sodium hydroxide 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 4-(2-酮基-3-甲基-1-苯并咪唑基)哌啶
  参考文献：
  名称：

  Discovery and SAR studies of a novel series of noncovalent cathepsin S inhibitors

  摘要：

  A novel series of competitive, reversible cathepsin S (Cats) inhibitors was discovered and optimized. The 4-(2-keto-1-benzimidazolinyl)-piperidin-1-yl moiety was found to be an effective replacement for the 4-arylpiperazin-1-yl group found in our earlier series of Cats inhibitors. This replacement imparted improved PK properties as well as decreased off-target activity. Optimization of the ketobenzimidazole moiety led to the discovery of the lead compound JNJ 10329670, which represents a novel class of selective, noncovalent, reversible, and orally bioavailable inhibitors of cathepsin S. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.045
• 作为产物：
  描述：

  4-[(2-硝基苯基)氨基]哌啶-1-羧酸乙酯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 吗丁啉杂质13
  参考文献：
  名称：

  新型BQCA和TBPB衍生的M1受体混合配体：正构咔巴酚差异调节部分激动。

  摘要：

  最近，对变构机制的研究已经使人们对G蛋白偶联受体（GPCR）的激活和信号传导过程有了更深入的了解。在这种情况下，毒蕈碱型乙酰胆碱受体（mAChRs）由于在变构调节研究中具有示范作用，因此具有很高的相关性。在这项工作中，我们比较和讨论了两组推定的双空间配体，这些配体旨在将卡巴胆碱与不同类型的变构体配体连接。我们选择了TBPB [1-（1'-（2-甲苯基）-1,4'-双哌啶-4-基）-1 H-苯并[ d ]咪唑-2-2 （3 H）-one]的导数作为M 1。选择性推定的双向配体，以及苄基喹诺酮羧酸（BQCA）的M 1衍生物正变构调节剂，改变变构和正构构件之间的距离。萤光素酶蛋白质互补测定法表明，必须仔细选择接头长度才能产生激动剂或拮抗剂行为。这些发现可能有助于设计偏向的信号传导和/或不同程度的功效。

  DOI：

  10.1002/cmdc.201900283

文献信息

• Synthesis and SAR studies of benzimidazolone derivatives as histamine H3-receptor antagonists
  作者：Qingbei Zeng、Stuart B. Rosenblum、Zhaoxia Yang、Yueheng Jiang、Kevin D. McCormick、Robert G. Aslanian、Luli Duguma、Joseph A. Kozlowski、Neng-Yang Shih、John A. Hey、Robert E. West、Walter A. Korfmacher、Michael Berlin、Christopher W. Boyce

  DOI：10.1016/j.bmcl.2013.08.012

  日期：2013.11

  A novel series of benzimidazolone-containing histamine H3-receptor antagonists were prepared and their structure–activity relationship was explored. These benzimidazolone analogs demonstrate potent H3-receptor binding affinities, no P450 enzyme inhibition, and strong H3 functional activity. Compound 1o exhibits the best overall profile with H3Ki = 0.95 nM and rat AUC = 12.9 μM h.

  制备了一系列新的含苯并咪唑酮的组胺H 3受体拮抗剂，并探讨了它们的结构-活性关系。这些苯并咪唑酮类似物显示出有效的H 3-受体结合亲和力，无P450酶抑制作用，并且具有强大的H 3功能活性。化合物1o表现出最佳的总体特征，H 3 K i  = 0.95 nM，大鼠AUC = 12.9μMh。
• Synthesis of (1-substituted piperidin-4-yl)-1<i>H</i>-benzimidazoles and (1-substituted piperidin-4-yl)-3,4-dihydroquinazolines as possible antihypertensive agents
  作者：Hiroyuki Obase、Haruki Takai、Masayuki Teranishi、Nobuhiro Nakamizo

  DOI：10.1002/jhet.5570200315

  日期：1983.5

  other heterocycles (2-cyanoamino, 2-ethoxy, and 2-methylbenzimidazole and 2-cyanoamino-3,4-dihydroquinazoline) has been made and a number of new piperidines (II) were synthesized as potential antihypertensive agents.

  通过用其他杂环（2-氰基氨基，2-乙氧基和2-甲基苯并咪唑和2-氰基氨基-3,4-二氢喹唑啉）取代苯并咪唑啉酮基团，对4-哌啶基苯并咪唑啉酮类（I）进行结构修饰，并且已经制备了许多新的哌啶（II）被合成为潜在的降压药。
• Piperidines
  申请人：Icagen, Inc.

  公开号：US20030171360A1

  公开（公告）日：2003-09-11

  Compounds, compositions and methods are provided which are useful in the treatment of diseases through the inhibition of sodium ion flux through voltage-dependent sodium channels. More particularly, the invention provides substituted piperidines, and compositions containing these compounds. Also provided are methods using the compounds of the invention for the treatment of central or peripheral nervous system disorders, particularly pain and chronic pain by blocking sodium channels associated with the onset or recurrance of the indicated conditions. The compounds, compositions and methods of the present invention are of particular use for treating neuropathic or inflammatory pain by the inhibition of ion flux through a channel that includes a PN3 subunit.

  提供了一种在治疗疾病中通过抑制电压依赖性钠通道的钠离子通量而有用的化合物、组合物和方法。更具体地，该发明提供了取代哌啶类化合物以及含有这些化合物的组合物。还提供了使用该发明的化合物治疗中枢或外周神经系统疾病的方法，特别是通过阻断与所示疾病的发作或复发有关的钠通道来治疗疼痛和慢性疼痛。本发明的化合物、组合物和方法特别适用于通过抑制包含PN3亚基的通道的离子通量来治疗神经病性或炎症性疼痛。
• PIPERIDINES
  申请人：Gross F. Michael

  公开号：US20080058376A1

  公开（公告）日：2008-03-06

  Compounds, compositions and methods are provided which are useful in the treatment of diseases through the inhibition of sodium ion flux through voltage-dependent sodium channels. More particularly, the invention provides substituted piperidines, and compositions containing these compounds. Also provided are methods using the compounds of the invention for the treatment of central or peripheral nervous system disorders, particularly pain and chronic pain by blocking sodium channels associated with the onset or recurrance of the indicated conditions. The compounds, compositions and methods of the present invention are of particular use for treating neuropathic or inflammatory pain by the inhibition of ion flux through a channel that includes a PN3 subunit.

  本发明提供了用于通过抑制电压依赖性钠通道中的钠离子通量来治疗疾病的化合物、组合物和方法。更具体地，本发明提供了取代哌啶的化合物和含有这些化合物的组合物。还提供了使用本发明的化合物治疗中枢或外周神经系统障碍，特别是疼痛和慢性疼痛的方法，通过阻断与所述病症的发作或复发相关的钠通道。本发明的化合物、组合物和方法特别适用于通过抑制包括PN3亚单位的通道中的离子通量来治疗神经病理性或炎症性疼痛。
• New ‘chemical probes’ to examine the role of the hFPRL1 (or ALXR) receptor in inflammation
  作者：Mike Frohn、Han Xu、Xiaoming Zou、Catherine Chang、Michele McElvaine、Matthew H. Plant、Min Wong、Philip Tagari、Randall Hungate、Roland W. Bürli

  DOI：10.1016/j.bmcl.2007.09.043

  日期：2007.12

  We report the development of the novel N-substituted benzimidazole 11 as a potent and selective human formyl peptide receptor-like 1 (hFPRL1) agonist. This compound and its less active enantiomer 12 were identified as useful tools for studying receptor function in vitro. (c) 2007 Elsevier Ltd. All rights reserved.