1-(4-Propylsulfonylpiperazin-1-yl)cyclohexane-1-carbonitrile | 1351676-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(4-Propylsulfonylpiperazin-1-yl)cyclohexane-1-carbonitrile
• CAS: 1351676-43-1
• 化学式: C₁₄H₂₅N₃O₂S
• 分子量: 299.437
• InChiKey: KSVHWPIAMVBBMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-Propylsulfonylpiperazin-1-yl)cyclohexane-1-carbonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到(1-(4-(propylsulfonyl)piperazin-1-yl)cyclohexyl)methanamine
  参考文献：
  名称：

  Design, synthesis, and SAR of N-((1-(4-(propylsulfonyl)piperazin-1-yl)cycloalkyl)methyl)benzamide inhibitors of glycine transporter-1

  摘要：

  The design, synthesis, and structure-activity relationships (SAR) of a series of N-((1-(4-(propylsulfonyl)piperazin-1-yl)cycloalkyl)methyl)benzamide inhibitors of glycine transporter-1 (GlyT-1) are described. Optimization of the benzamide and central ring components of the core scaffold led to the identification of a GlyT-1 inhibitor that demonstrated in vivo activity in a rodent cerebral spinal fluid (CSF) glycine model. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.006
• 作为产物：
  描述：

  tert-butyl 4-(propylsulfonyl)piperazine-1-carboxylate 在 sodium metabisulfite 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 1-(4-Propylsulfonylpiperazin-1-yl)cyclohexane-1-carbonitrile
  参考文献：
  名称：

  Design, synthesis, and SAR of N-((1-(4-(propylsulfonyl)piperazin-1-yl)cycloalkyl)methyl)benzamide inhibitors of glycine transporter-1

  摘要：

  The design, synthesis, and structure-activity relationships (SAR) of a series of N-((1-(4-(propylsulfonyl)piperazin-1-yl)cycloalkyl)methyl)benzamide inhibitors of glycine transporter-1 (GlyT-1) are described. Optimization of the benzamide and central ring components of the core scaffold led to the identification of a GlyT-1 inhibitor that demonstrated in vivo activity in a rodent cerebral spinal fluid (CSF) glycine model. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.006

文献信息

• GLYCINE TRANSPORTER-1 INHIBITORS, METHODS OF MAKING THEM, AND USES THEREOF
  申请人：CIOFFI Christopher L.

  公开号：US20110312931A1

  公开（公告）日：2011-12-22

  The compounds of the present invention are represented by the following formula (I): wherein the substituents R 1 , R 2 , R 3 , R 4 , (R 5 ) m , R 6 , A, X, and Y are as defined herein. The compounds are useful in methods of treating a disorder which is created by or is dependent upon inhibiting GlyT-1.

  本发明的化合物由以下公式（I）表示：其中，取代基R1、R2、R3、R4、（R5）m、R6、A、X和Y的定义如本文所述。这些化合物可用于治疗由抑制GlyT-1引起或依赖于GlyT-1抑制的疾病的方法。
• US9045445B2
  申请人：——

  公开号：US9045445B2

  公开（公告）日：2015-06-02
• [EN] GLYCINE TRANSPORTER-1 INHIBITORS, METHODS OF MAKING THEM, AND USES THEREOF<br/>[FR] INHIBITEURS DU TRANSPORTEUR 1 DE LA GLYCINE, PROCÉDÉS DE FABRICATION ASSOCIÉS, ET UTILISATIONS ASSOCIÉES
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2011153359A1

  公开（公告）日：2011-12-08

  The compounds of the present invention are represented by the following formula (I): wherein the substituents R1, R2, R3, R4, (R5)m, R6, A, X, and Y are as defined herein. The compounds are useful in methods of treating a disorder which is created by or is dependent upon inhibiting GlyT-1.
• Design, synthesis, and SAR of N-((1-(4-(propylsulfonyl)piperazin-1-yl)cycloalkyl)methyl)benzamide inhibitors of glycine transporter-1
  作者：Christopher L. Cioffi、Mark A. Wolf、Peter R. Guzzo、Kashinath Sadalapure、Visweswaran Parthasarathy、Dattatraya Dethe、Jun-Ho Maeng、Edmund Carulli、David T.J. Loong、Xiao Fang、Min Hu、Priya Gupta、Mark Chung、Mei Bai、Nick Moore、Michele Luche、Yuri Khmelnitsky、Patrick L. Love、Megan A. Watson、Andrew J. Mhyre、Shuang Liu

  DOI：10.1016/j.bmcl.2013.01.006

  日期：2013.3

  The design, synthesis, and structure-activity relationships (SAR) of a series of N-((1-(4-(propylsulfonyl)piperazin-1-yl)cycloalkyl)methyl)benzamide inhibitors of glycine transporter-1 (GlyT-1) are described. Optimization of the benzamide and central ring components of the core scaffold led to the identification of a GlyT-1 inhibitor that demonstrated in vivo activity in a rodent cerebral spinal fluid (CSF) glycine model. (c) 2013 Elsevier Ltd. All rights reserved.