4-nitrobenzyl allyl(piperidin-4-yl)carbamate | 413603-60-8

• 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: 4-nitrobenzyl allyl(piperidin-4-yl)carbamate
• 英文别名: (4-nitrophenyl)methyl N-piperidin-4-yl-N-prop-2-enylcarbamate
• CAS: 413603-60-8
• 化学式: C₁₆H₂₁N₃O₄
• 分子量: 319.36
• InChiKey: WXVRHAZCBVFIBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-nitrobenzyl allyl(piperidin-4-yl)carbamate 、 (3a'S,4'R,5'S)-5'-phenyltetrahydro-3'H-spiro[cyclohexane-1,2'-pyrrolo[1,2-b]isoxazole]-4'-carbaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 生成 C₃₄H₄₄N₄O₅
  参考文献：
  名称：

  CCR5 antagonists: bicyclic isoxazolidines as conformationally constrained N-1-substituted pyrrolidines

  摘要：

  A series of CCR5 antagonists containing bicyclic isoxazolidines was generated through a nitrone mediated cycloaddition with olefins bearing the preferred pharmacophores previously described. Potent antagonists (3 and 16) were generated with enhanced affinity for the CCR5 receptor while maintaining antiviral activity against HIV. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00835-6
• 作为产物：
  描述：

  1-(tert-butoxycarbonyl)-4-(N-(4-nitrobenzyloxycarbonyl)-N-(allyl)amino)piperidine 在 三氟乙酸 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 4-nitrobenzyl allyl(piperidin-4-yl)carbamate
  参考文献：
  名称：

  [EN] PYROLLIDINE-BASED COMPOUNDS
  [FR] COMPOSÉS À BASE DE PYROLLIDINE

  摘要：

  本发明揭示了式（I）的化合物或其药学上可接受的衍生物、盐或前药，可以抑制HIV复制。

  公开号：

  WO2009089659A1

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AS CCR5 ANTAGONISTS<br/>[FR] COMPOSES HETEROCYCLIQUES UTILISES EN TANT QU'ANTAGONISTES DU CCR5
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004055011A1

  公开（公告）日：2004-07-01

  The present invention relates to compounds of the following formula (I), or pharmaceutically acceptable derivatives thereof, useful in the treatment of CCR5-related diseases and disorders, for example, useful in the inhibition of HIV replication, the prevention or treatment of an HIV infection, and in the treatment of the resulting acquired immune deficiency syndrome (AIDS).

  本发明涉及以下式(I)的化合物，或其药学上可接受的衍生物，在CCR5相关疾病和疾病的治疗中有用，例如，在抑制HIV复制、预防或治疗HIV感染以及治疗由此导致的获得性免疫缺陷综合症（AIDS）方面有用。
• Heterocyclic compounds as ccr5 antagonists
  申请人：Aquino Joseph Christopher

  公开号：US20060052595A1

  公开（公告）日：2006-03-09

  The present invention relates to compounds of formula (I), or pharmaceutically acceptable derivatives thereof, useful in the treatment of CCR5-related diseases and disorders, for example, useful in the inhibition of HIV replication, the prevention or treatment of an HIV infection, and in the treatment of the resulting acquired immune deficiency syndrome (AIDS).

  本发明涉及公式（I）的化合物或其药学上可接受的衍生物，用于治疗CCR5相关疾病和障碍，例如，在抑制HIV复制方面有用，预防或治疗HIV感染，并用于治疗由此导致的获得性免疫缺陷综合症（AIDS）。
• HETEROCYCLIC COMPOUNDS AS CCR5 ANTAGONISTS
  申请人：AQUINO Christopher Joseph

  公开号：US20090053172A1

  公开（公告）日：2009-02-26

  The present invention relates to compounds of formula (I), or pharmaceutically acceptable derivatives thereof, useful in the treatment of CCR5-related diseases and disorders, for example, useful in the inhibition of HIV replication, the prevention or treatment of an HIV infection, and in the treatment of the resulting acquired immune deficiency syndrome (AIDS).

  本发明涉及式(I)化合物或其药学上可接受的衍生物，用于治疗CCR5相关的疾病和障碍，例如，用于抑制HIV复制，预防或治疗HIV感染，并用于治疗由此导致的获得性免疫缺陷综合症（AIDS）。
• Studies on the structure–activity relationship of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists. Part 2: Discovery of highly potent anti-HIV agents
  作者：Ben Li、Eric Dale Jones、Enkun Zhou、Li Chen、Dean Cameron Baylis、Shanghai Yu、Miao Wang、Xing He、Jonathan Alan Victor Coates、David Ian Rhodes、Gang Pei、John Joseph Deadman、Xin Xie、Dawei Ma

  DOI：10.1016/j.bmcl.2010.05.046

  日期：2010.9

  Modification of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists revealed that introducing a fluoro group at the 3-position of the 3-phenyl group to reduce metabolism did not adversely affect the high potency against HIV infection, and that replacing the piperidine ring with a tropane ring could deliver the most potent anti-HIV agents. Stereochemistry of the substituted tropane ring is essential for maintaining the potent anti-HIV activity because only exo-isomers displayed subnanomolar whole cell activity. (C) 2010 Elsevier Ltd. All rights reserved.
• Syntheses and biological evaluation of 5-(piperidin-1-yl)-3-phenyl-pentylsulfones as CCR5 antagonists
  作者：K. Shankaran、Karla L. Donnelly、Shrenik K. Shah、Charles G. Caldwell、Ping Chen、Paul E. Finke、Bryan Oates、Malcolm MacCoss、Sander G. Mills、Julie A. DeMartino、Sandra L. Gould、Lorraine Malkowitz、Salvatore J. Siciliano、Martin S. Springer、Gloria Kwei、Anthony Carella、Gwen Carver、Renee Danzeisen、Daria Hazuda、Karen Holmes、Joseph Kessler、Janet Lineberger、Michael D. Miller、Emilio A. Emini、William A. Schleif

  DOI：10.1016/j.bmcl.2004.03.112

  日期：2004.7

  Cellular proliferation of HIV-1 requires the cooperative assistance of both the CCR5 and CD4 receptors. Our medicinal chemistry efforts in this area have resulted in the identification of N-alkyl piperidine sulfones as CCR5 antagonists. These compounds display potent binding and show antiviral properties in HIV-1 spread cell-based assays. (C) 2004 Published by Elsevier Ltd.