methanesulfonic acid 8-benzyl-8-aza-bicyclo[3.2.1]oct-3-ylester | 877457-31-3

• 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: methanesulfonic acid 8-benzyl-8-aza-bicyclo[3.2.1]oct-3-ylester
• 英文别名: Methanesulfonic acid 8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl ester；(8-benzyl-8-azabicyclo[3.2.1]octan-3-yl) methanesulfonate
• CAS: 877457-31-3
• 化学式: C₁₅H₂₁NO₃S
• 分子量: 295.403
• InChiKey: WTQRRIIMSHWAIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 8-benzyl-8-aza-bicyclo[3.2.1]oct-3-ylester 在 potassium carbonate 、 红铝 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 22.0h， 生成 3-(1-Benzyl-tropin-4-yl)-5,5-diphenyl-imidazolidin-2-one
  参考文献：
  名称：

  Discovery of Diaryl Imidazolidin-2-one Derivatives, a Novel Class of Muscarinic M3 Selective Antagonists (Part 1)

  摘要：

  Pharmacophore-based structural identification, synthesis, and structure-activity relationships of a new class of muscarinic M3 receptor antagonists, the diaryl imidazolidin-2-one derivatives, are described. The versatility of the discovered scaffold allowed for several structural modifications that resulted in the discovery of two distinct classes of compounds, specifically a class of tertiary amine derivatives (potentially useful for the treatment of overactive bladder by oral administration) and a class of quaternary ammonium salt derivatives (potentially useful for the treatment of respiratory diseases by the inhalation route of administration). In this paper, we describe the synthesis and biological activity of tertiary amine derivatives. For these compounds, selectivity for the M3 receptor toward the M2 receptor was crucial, because the M2 receptor subtype is mainly responsible for adverse systemic side effects of currently marketed muscarinic antagonists. Compound 50 showed the highest selectivity versus M2 receptor, with binding affinity for M3 receptor K-i = 4.8 nM and for M2 receptor K-i = 1141 nM. Functional in vitro studies on selected compounds confirmed the antagonist activity toward the M3 receptor and functional selectivity toward the M2 receptor.

  DOI：

  10.1021/jm061159a
• 作为产物：
  描述：

  N-benzyl-tropin-4-ol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methanesulfonic acid 8-benzyl-8-aza-bicyclo[3.2.1]oct-3-ylester
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS HAVING AN ANTI-BACTERIAL ACTIVITY
  [FR] NOUVEAUX COMPOSES PRESENTANT UNE ACTIVITE ANTIBACTERIENNE

  摘要：

  本发明描述了具有通式(I)的新型抗菌化合物。这些化合物在其他方面，尤其是作为DNA促旋酶抑制剂，具有研究价值。

  公开号：

  WO2006021448A1

文献信息

• [EN] CHEMOKING RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DES RÉCEPTEURS DE CHIMIOKINES
  申请人：ABBOTT LAB

  公开号：WO2013010453A1

  公开（公告）日：2013-01-24

  Disclosed herein are chemokine receptor antagonists of formula (I) wherein G1, X1, X2, and X3 are as defined in the specification. Compositions comprising such compounds; and methods for treating conditions and disorders using such compounds and compositions are also described.

  本文揭示了化学受体拮抗剂的化学式(I)，其中G1、X1、X2和X3如规范中所定义。还描述了包含这种化合物的组合物；以及使用这种化合物和组合物治疗疾病和疾病的方法。
• Novel Compounds Having an Anti-Bacterial Activity
  申请人：Pierau Sabine

  公开号：US20070244103A1

  公开（公告）日：2007-10-18

  The present invention describes novel anti-bacterial compounds of formula (I). Q-A-R 3 (I) These compounds are, amongst others, of interest as inhibitors of DNA gyrase.

  本发明描述了式(I)的新型抗菌化合物。Q-A-R3(I)这些化合物是DNA旋转酶抑制剂等方面的有趣化合物。
• NOVEL COMPOUNDS HAVING AN ANTI-BACTERIAL ACTIVITY
  申请人：Morphochem Aktiengesellschaft Für Kombinatorische Chemie

  公开号：EP1781650A1

  公开（公告）日：2007-05-09
• [EN] NOVEL COMPOUNDS HAVING AN ANTI-BACTERIAL ACTIVITY<br/>[FR] NOUVEAUX COMPOSES PRESENTANT UNE ACTIVITE ANTIBACTERIENNE
  申请人：CHEMIE MORPHOCHEM AG FUER KOMB

  公开号：WO2006021448A1

  公开（公告）日：2006-03-02

  The present invention describes novel anti-bacterial compounds of formula (I). These compounds are, amongst others, of interest as inhibitors of DNA gyrase.

  本发明描述了具有通式(I)的新型抗菌化合物。这些化合物在其他方面，尤其是作为DNA促旋酶抑制剂，具有研究价值。
• Discovery of Diaryl Imidazolidin-2-one Derivatives, a Novel Class of Muscarinic M3 Selective Antagonists (Part 1)
  作者：Ilaria Peretto、Roberto Forlani、Claudia Fossati、Giuseppe A. M. Giardina、Alessandra Giardini、Matilde Guala、Elena La Porta、Paola Petrillo、Stefano Radaelli、Luigi Radice、Luca F. Raveglia、Enza Santoro、Roberta Scudellaro、Francesca Scarpitta、Chiara Bigogno、Paola Misiano、Giulio M. Dondio、Andrea Rizzi、Elisabetta Armani、Gabriele Amari、Maurizio Civelli、Gino Villetti、Riccardo Patacchini、Marco Bergamaschi、Maurizio Delcanale、Carolina Salcedo、Andrés G. Fernández、Bruno P. Imbimbo

  DOI：10.1021/jm061159a

  日期：2007.4.1

  Pharmacophore-based structural identification, synthesis, and structure-activity relationships of a new class of muscarinic M3 receptor antagonists, the diaryl imidazolidin-2-one derivatives, are described. The versatility of the discovered scaffold allowed for several structural modifications that resulted in the discovery of two distinct classes of compounds, specifically a class of tertiary amine derivatives (potentially useful for the treatment of overactive bladder by oral administration) and a class of quaternary ammonium salt derivatives (potentially useful for the treatment of respiratory diseases by the inhalation route of administration). In this paper, we describe the synthesis and biological activity of tertiary amine derivatives. For these compounds, selectivity for the M3 receptor toward the M2 receptor was crucial, because the M2 receptor subtype is mainly responsible for adverse systemic side effects of currently marketed muscarinic antagonists. Compound 50 showed the highest selectivity versus M2 receptor, with binding affinity for M3 receptor K-i = 4.8 nM and for M2 receptor K-i = 1141 nM. Functional in vitro studies on selected compounds confirmed the antagonist activity toward the M3 receptor and functional selectivity toward the M2 receptor.