4-(1-Cyano-cyclohexyl)-piperazine-1-carboxylic acid tert-butyl ester | 511538-85-5

• 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: 4-(1-Cyano-cyclohexyl)-piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-(1-cyanocyclohexyl)piperazine-1-carboxylate
• CAS: 511538-85-5
• 化学式: C₁₆H₂₇N₃O₂
• 分子量: 293.409
• InChiKey: YTSJLZAYHRMWSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(1-Cyano-cyclohexyl)-piperazine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(1-Isobutyl-cyclohexyl)-piperazine
  参考文献：
  名称：

  Privileged structure based ligands for melanocortin receptors—4,4-Disubstituted piperidine derivatives

  摘要：

  Homologation and cyclization back to the chiral methine of compound 3 yields achiral 4,4-disubstituted piperidine privileged structures (e.g., 8a) useful in the construction of melanocortin 4 receptor (MC4R) ligands. The piperidine nitrogen was replaced with carbon, oxygen, sulfur, and sulfone with minor erosion of binding. The methyl cyclohexane substituent was the most potent while significant affinity was still seen for smaller lipophilic groups such as ethyl. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.016
• 作为产物：
  描述：

  三甲基氰硅烷 、 环己酮 、 N-Boc-哌嗪 在 zinc(II) iodide 作用下， 生成 4-(1-Cyano-cyclohexyl)-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Privileged structure based ligands for melanocortin receptors—4,4-Disubstituted piperidine derivatives

  摘要：

  Homologation and cyclization back to the chiral methine of compound 3 yields achiral 4,4-disubstituted piperidine privileged structures (e.g., 8a) useful in the construction of melanocortin 4 receptor (MC4R) ligands. The piperidine nitrogen was replaced with carbon, oxygen, sulfur, and sulfone with minor erosion of binding. The methyl cyclohexane substituent was the most potent while significant affinity was still seen for smaller lipophilic groups such as ethyl. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.016

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。
• US7314879B2
  申请人：——

  公开号：US7314879B2

  公开（公告）日：2008-01-01
• 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.