4-(2,3-二氢-2-氧代-1H-苯并咪唑-1-基)哌啶-1-羧酸乙酯 | 53786-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 4-(2,3-二氢-2-氧代-1H-苯并咪唑-1-基)哌啶-1-羧酸乙酯
• 英文名称: 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-piperidine-1-carboxylic acid ethyl ester
• 英文别名: 4-(2-oxo-2,3-dihydrobenzoimidazol-1-yl)piperidine-1-carboxylic acid ethyl ester；ethyl 4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate；Ethyl 4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)piperidine-1-carboxylate；ethyl 4-(2-oxo-3H-benzimidazol-1-yl)piperidine-1-carboxylate
• CAS: 53786-47-3
• 化学式: C₁₅H₁₉N₃O₃
• 分子量: 289.334
• InChiKey: GXSAIQHDWSYUNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-(2,3-二氢-2-氧代-1H-苯并咪唑-1-基)哌啶-1-羧酸乙酯 在 4-二甲氨基吡啶 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  苯并咪唑酮衍生物作为组胺H 3受体拮抗剂的合成与合成孔径雷达研究

  摘要：

  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。

  DOI：

  10.1016/j.bmcl.2013.08.012
• 作为产物：
  描述：

  4-(2-Iodo-phenylamino)-piperidine-1-carboxylic acid ethyl ester 在 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 醋酸异丙酯 、 异丙醇 为溶剂， 反应 73.17h， 生成 4-(2,3-二氢-2-氧代-1H-苯并咪唑-1-基)哌啶-1-羧酸乙酯
  参考文献：
  名称：

  Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization

  摘要：

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.

  DOI：

  10.1021/ol061233j

文献信息

• Use of a compound having a monogalactosyldiacylglycerol synthase inhibitory activity as herbicide or algaecide, herbicide and algaecide compositions
  申请人：Commissariat à l'Energie Atomique

  公开号：EP1997381A1

  公开（公告）日：2008-12-03

  The invention relates to the use of compounds having a monogalactosyldiacylglycerol (MGDG) synthase inhibitory activity as herbicide or algaecide, and to herbicide and algaecide compositions containing at least one of these compounds.

  该发明涉及将具有单半乳糖二酰基甘油（MGDG）合成酶抑制活性的化合物用作除草剂或藻类杀灭剂，并且涉及含有至少一种这些化合物的除草剂和藻类杀灭剂组合物。
• Compounds with antiparasitic activity, applications thereof to the treatment of infectious diseases caused by apicomplexans
  申请人：Commissariat à l'Energie Atomique

  公开号：EP1997805A1

  公开（公告）日：2008-12-03

  The Invention relates to compounds having an antiparasitic activity, and to their use as a drug, in particular as a drug for the prevention and/or treatment of parasitic diseases caused by apicomplexans. The invention also relates to pharmaceutical compositions containing those compounds.

  这项发明涉及具有抗寄生虫活性的化合物，以及它们作为药物的用途，特别是作为预防和/或治疗由顶复合体寄生虫引起的寄生虫病的药物。该发明还涉及含有这些化合物的药物组合物。
• Novel BQCA‐ and TBPB‐Derived M ₁ Receptor Hybrid Ligands: Orthosteric Carbachol Differentially Regulates Partial Agonism
  作者：Simon Schramm、Luca Agnetta、Marcel Bermudez、Hubert Gerwe、Matthias Irmen、Janine Holze、Timo Littmann、Gerhard Wolber、Christian Tränkle、Michael Decker

  DOI：10.1002/cmdc.201900283

  日期：2019.7.17

  G protein‐coupled receptor (GPCR) activation and signaling processes. In this context, muscarinic acetylcholine receptors (mAChRs) are highly relevant due to their exemplary role in the study of allosteric modulation. In this work, we compare and discuss two sets of putatively dualsteric ligands, which were designed to connect carbachol to different types of allosteric ligands. We chose derivatives of TBPB [1‐(1′‐(2‐tolyl)‐1

  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。
• Benzodiazepine calcitonin gene-related peptide (CGRP) receptor antagonists: Optimization of the 4-substituted piperidine
  作者：Christopher S. Burgey、Craig A. Stump、Diem N. Nguyen、James Z. Deng、Amy G. Quigley、Beth R. Norton、Ian M. Bell、Scott D. Mosser、Christopher A. Salvatore、Ruth Z. Rutledge、Stefanie A. Kane、Kenneth S. Koblan、Joseph P. Vacca、Samuel L. Graham、Theresa M. Williams

  DOI：10.1016/j.bmcl.2006.07.044

  日期：2006.10

  In our continuing effort to identify CGRP receptor antagonists for the acute treatment of migraine, we have undertaken a study to evaluate alternative 4-substituted piperidines to the lead dihydroquinazolinone 1. In this regard, we have identified the piperidinyl-azabenzimidazolone and phenylimidazolinone structures which, when incorporated into the benzodiazepine core, afford potent CGRP receptor antagonists (e.g., 18 and 29). These studies produced a potent analog (18) which overcomes the instability issues associated with the lead structure 1. A general pharmacophore for the 4-substituted piperidine component of these CGRP receptor antagonists is also presented. (c) 2006 Elsevier Ltd. All rights reserved.
• Discovery and SAR studies of a novel series of noncovalent cathepsin S inhibitors
  作者：Darin J. Gustin、Clark A. Sehon、Jianmei Wei、Hui Cai、Steven P. Meduna、Haripada Khatuya、Siquan Sun、Yin Gu、Wen Jiang、Robin L. Thurmond、Lars Karlsson、James P. Edwards

  DOI：10.1016/j.bmcl.2005.01.045

  日期：2005.3

  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.