3-benzyl-5-(piperidin-4-yl)-1,2,4-oxadiazole | 280110-72-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-benzyl-5-(piperidin-4-yl)-1,2,4-oxadiazole
• 英文别名: 4-(3-benzyl-1,2,4-oxadiazol-5-yl)piperidine；3-benzyl-5-piperidin-4-yl-1,2,4-oxadiazole
• CAS: 280110-72-7
• 化学式: C₁₄H₁₇N₃O
• mdl: MFCD11124267
• 分子量: 243.308
• InChiKey: NKAWZEXAFWZNLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyl-5-(piperidin-4-yl)-1,2,4-oxadiazole 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N¹-(3-thiophenylmethyl)-4-[3-benzyl-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
  参考文献：
  名称：

  Antiproliferative 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, a new tubulin inhibitor chemotype

  摘要：

  We discovered a new chemical class of antiproliferative agents, 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides. SAR-guided optimization of the two distinct terminal fragments yielded a compound with 120 nM potency in an antiproliferative assay. Biological activity profile studies (COMPARE analysis) demonstrated that 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides act as tubulin inhibitors, and this conclusion was confirmed via biochemical assays with pure tubulin and demonstration of increased numbers of mitotic cells following treatment of a leukemia cell line. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.089
• 作为产物：
  描述：

  N’-羟基-2-苯基ETHANIMIDAMIDE 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 3-benzyl-5-(piperidin-4-yl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Antiproliferative 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, a new tubulin inhibitor chemotype

  摘要：

  We discovered a new chemical class of antiproliferative agents, 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides. SAR-guided optimization of the two distinct terminal fragments yielded a compound with 120 nM potency in an antiproliferative assay. Biological activity profile studies (COMPARE analysis) demonstrated that 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides act as tubulin inhibitors, and this conclusion was confirmed via biochemical assays with pure tubulin and demonstration of increased numbers of mitotic cells following treatment of a leukemia cell line. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.089

文献信息

• [EN] INDANE COMPOUNDS AS CCR5 ANTAGONISTS<br/>[FR] COMPOSES INDANE UTILISES COMME ANTAGONISTES DE CCR5
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004055012A1

  公开（公告）日：2004-07-01

  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，或其药用可接受的衍生物，用于治疗CCR5相关疾病和障碍，例如，用于抑制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（艾滋病）。
• Chemical compounds
  申请人：Faull Alan

  公开号：US20070167442A1

  公开（公告）日：2007-07-19

  Compounds of formula (I): compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating CCR5 receptor activity in a warm blooded animal).

  公式（I）的化合物：包括它们的组合物，制备它们的方法以及它们在医学疗法中的用途（例如在温血动物中调节CCR5受体活性）。
• Investigation around the Oxadiazole Core in the Discovery of a New Chemotype of Potent and Selective FXR Antagonists
  作者：Carmen Festa、Claudia Finamore、Silvia Marchianò、Francesco Saverio Di Leva、Adriana Carino、Maria Chiara Monti、Federica del Gaudio、Sara Ceccacci、Vittorio Limongelli、Angela Zampella、Stefano Fiorucci、Simona De Marino

  DOI：10.1021/acsmedchemlett.8b00534

  日期：2019.4.11

  antagonists might be useful in the treatment of cholestasis and related metabolic disorders. In this paper, we report the discovery of a new chemotype of FXR antagonists featured by a 3,5-disubstituted oxadiazole core. In total, 35 new derivatives were designed and synthesized, and notably, compounds 3f and 13, containing a piperidine ring, displayed the best antagonistic activity against FXR with

  最近的发现表明，法尼醇X受体（FXR）拮抗剂可能在胆汁淤积症和相关代谢紊乱的治疗中有用。在本文中，我们报告了以3,5-二取代的恶二唑核心为特征的新型FXR拮抗剂化学型的发现。总共设计并合成了35种新的衍生物，尤其是含有哌啶环的化合物3f和13对FXR表现出最佳的拮抗活性，并具有有希望的细胞效价（IC 50分别为0.58±0.27和0.127±0.02μM） 。优异的药代动力学特性使化合物3f成为本研究中鉴定出的最有希望的先导。
• Indane compounds as ccr5 antagonists
  申请人：Youngman Michael

  公开号：US20060047116A1

  公开（公告）日：2006-03-02

  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，用于抑制HIV复制，预防或治疗HIV感染，并用于治疗导致的获得性免疫缺陷综合症（AIDS）。
• Cyclopropyl compounds as ccr5 antagonists
  申请人：Peckham Poole Jennifer

  公开号：US20060052408A1

  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).

  本发明涉及式（I）的化合物或其药学上可接受的衍生物，用于治疗与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）。