benzyl (3S)-3-[tert-butoxycarbonyl(methyl)amino]piperidine-1-carboxylate | 1124199-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (3S)-3-[tert-butoxycarbonyl(methyl)amino]piperidine-1-carboxylate
• 英文别名: (S)-benzyl 3-(tert-butoxycarbonyl(methyl)amino)piperidine-1-carboxylate；benzyl (3S)-3-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]piperidine-1-carboxylate
• CAS: 1124199-24-1
• 化学式: C₁₉H₂₈N₂O₄
• 分子量: 348.442
• InChiKey: AWSLVKRHDKOLLJ-INIZCTEOSA-N

物化性质

• 沸点：
  455.6±44.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (3S)-3-[tert-butoxycarbonyl(methyl)amino]piperidine-1-carboxylate 在 N-甲基吗啉 、 盐酸 、 palladium 10% on activated carbon 、 甲酸铵 、 三乙酰氧基硼氢化钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 生成 tert-butyl (S)-1-((S)-1-cyclohexyl-2-(methyl((S)-1-phenethylpiperidin-3-yl)amino)-2-oxoethylamino)-1-oxopropan-2-yl(methyl)carbamate
  参考文献：
  名称：

  Discovery of aminopiperidine-based Smac mimetics as IAP antagonists

  摘要：

  A series of structurally unique Smac mimetics that act as antagonists of inhibitor of apoptosis proteins (IAPs) has been discovered. While most previously described Smac mimetics contain the proline ring (or a similar cyclic motif) found in Smac, a key feature of the compounds described herein is that this ring has been removed. Despite this, compounds in this series potently bind to cIAP1 and elicit the expected phenotype of cIAP1 inhibition in cancer cells. Marked selectivity for cIAP1 over XIAP is observed for these compounds, which is attributed to a slight difference in the binding groove between the two proteins and the resulting steric interactions with the inhibitors. XIAP binding can be improved by constraining the inhibitor so that these unfavorable steric interactions are minimized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.109
• 作为产物：
  描述：

  (S)-3-Boc-氨基哌啶 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 0.08h， 生成 benzyl (3S)-3-[tert-butoxycarbonyl(methyl)amino]piperidine-1-carboxylate
  参考文献：
  名称：

  Discovery of aminopiperidine-based Smac mimetics as IAP antagonists

  摘要：

  A series of structurally unique Smac mimetics that act as antagonists of inhibitor of apoptosis proteins (IAPs) has been discovered. While most previously described Smac mimetics contain the proline ring (or a similar cyclic motif) found in Smac, a key feature of the compounds described herein is that this ring has been removed. Despite this, compounds in this series potently bind to cIAP1 and elicit the expected phenotype of cIAP1 inhibition in cancer cells. Marked selectivity for cIAP1 over XIAP is observed for these compounds, which is attributed to a slight difference in the binding groove between the two proteins and the resulting steric interactions with the inhibitors. XIAP binding can be improved by constraining the inhibitor so that these unfavorable steric interactions are minimized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.109

文献信息

• [EN] HETEROCYCLIC TYROSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE TYROSINE KINASE HÉTÉROCYCLIQUES
  申请人：BIOGEN IDEC INC

  公开号：WO2012058645A8

  公开（公告）日：2012-06-28
• Discovery of DS34942424: An orally potent analgesic without mu opioid receptor agonist activity
  作者：Tsuyoshi Arita、Masayoshi Asano、Kazufumi Kubota、Yuki Domon、Nobuo Machinaga、Kousei Shimada

  DOI：10.1016/j.bmc.2020.115714

  日期：2020.11

  We identified (5'S)-10'-fluoro-6'-methyl-5',6'-dihydro-3'H-spiro[cyclopropane-1,4'-[2,6]diaza[2,5]methano [2,6]benzodiazonin]-7'(1'H)-one, 22b (DS34942424) with a unique and original bicyclic skeleton. 22b showed an orally potent analgesic in the acetic acid-induced writhing test and formalin test in ddY mice without sedation. Moreover, 22b did not exhibit mu opioid receptor agonist activity.
• HETEROCYCLIC TYROSINE KINASE INHIBITORS
  申请人：Biogen MA Inc.

  公开号：US20170027956A1

  公开（公告）日：2017-02-02

  The present invention provides compounds useful as inhibitors of Tec family kinases, compositions thereof, and methods of using the same.
• US9273028B2
  申请人：——

  公开号：US9273028B2

  公开（公告）日：2016-03-01
• Discovery of aminopiperidine-based Smac mimetics as IAP antagonists
  作者：Edward J. Hennessy、Jamal C. Saeh、Li Sha、Terry MacIntyre、Haiyun Wang、Nicholas A. Larsen、Brian M. Aquila、Andrew D. Ferguson、Naomi M. Laing、Charles A. Omer

  DOI：10.1016/j.bmcl.2011.12.109

  日期：2012.2

  A series of structurally unique Smac mimetics that act as antagonists of inhibitor of apoptosis proteins (IAPs) has been discovered. While most previously described Smac mimetics contain the proline ring (or a similar cyclic motif) found in Smac, a key feature of the compounds described herein is that this ring has been removed. Despite this, compounds in this series potently bind to cIAP1 and elicit the expected phenotype of cIAP1 inhibition in cancer cells. Marked selectivity for cIAP1 over XIAP is observed for these compounds, which is attributed to a slight difference in the binding groove between the two proteins and the resulting steric interactions with the inhibitors. XIAP binding can be improved by constraining the inhibitor so that these unfavorable steric interactions are minimized. (C) 2011 Elsevier Ltd. All rights reserved.