4-phenoxynaphthalenylacetonitrile | 192213-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-phenoxynaphthalenylacetonitrile
• 英文别名: 1-cyanomethyl-4-phenoxynaphthalene；(4-Phenoxynaphthalen-1-yl)acetonitrile；2-(4-phenoxynaphthalen-1-yl)acetonitrile
• CAS: 192213-94-8
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: HIHYIOZMUMCIQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenoxynaphthalenylacetonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2-(1-phenoxynaphthalen-4-yl)ethylamine
  参考文献：
  名称：

  Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1

  摘要：

  3-Iodothyronamine (1, T(1)AM) is a naturally occurring derivative of thyroid hormone that can potently activate the orphan G protein-coupled receptor (GPCR) known as the trace amine-associated receptor 1 (TAAR(1)). We have previously found that modifying the outer ring of the phenoxyphenethylamine core scaffold of 1 can improve potency and provide potent agonists. In this study, we explored the tolerance of rat and mouse TAAR(1) (rTAAR(1) and mTAAR(1)) for structural modifications in the ethylamine portion of 1. We found that incorporating unsaturated hydrocarbon substituents and polar, hydrogen-bond-accepting groups were beneficial for rTAAR(1) and mTAAR(1), respectively, providing compounds that were equipotent or more potent than 1. Additionally, we have discovered that a naphthyl group is an excellent isosteric replacement for the iodophenyl ring of 1.

  DOI：

  10.1021/jm0700417
• 作为产物：
  描述：

  4-phenoxynaphthaldehyde 在 sodium tetrahydroborate 、 氯化亚砜 、 四氯化钛 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 4-phenoxynaphthalenylacetonitrile
  参考文献：
  名称：

  Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1

  摘要：

  3-Iodothyronamine (1, T(1)AM) is a naturally occurring derivative of thyroid hormone that can potently activate the orphan G protein-coupled receptor (GPCR) known as the trace amine-associated receptor 1 (TAAR(1)). We have previously found that modifying the outer ring of the phenoxyphenethylamine core scaffold of 1 can improve potency and provide potent agonists. In this study, we explored the tolerance of rat and mouse TAAR(1) (rTAAR(1) and mTAAR(1)) for structural modifications in the ethylamine portion of 1. We found that incorporating unsaturated hydrocarbon substituents and polar, hydrogen-bond-accepting groups were beneficial for rTAAR(1) and mTAAR(1), respectively, providing compounds that were equipotent or more potent than 1. Additionally, we have discovered that a naphthyl group is an excellent isosteric replacement for the iodophenyl ring of 1.

  DOI：

  10.1021/jm0700417

文献信息

• Naphthyl acetamides as sPLA.sub.2 inhibitors
  申请人：Eli Lilly and Company

  公开号：US06160175A1

  公开（公告）日：2000-12-12

  A class of novel naphthyl acetamide compounds is disclosed together with the use of such compounds for inhibiting sPLA.sub.2 mediated release of fatty acids for treatment of conditions such as septic shock.

  本文披露了一类新型萘乙酰胺化合物，以及利用这些化合物抑制sPLA.sub.2介导的脂肪酸释放，用于治疗诸如感染性休克等疾病的方法。
• Thyronamine derivatives and analogs and methods of use thereof
  申请人：Scanlan S. Thomas

  公开号：US20050096485A1

  公开（公告）日：2005-05-05

  Thyronamine derivatives and analogs, methods of using such compounds, and pharmaceutical compositions containing them are disclosed. Methods of preparing such compounds are also disclosed

  本发明揭示了甲状腺胺衍生物和类似物，使用这些化合物的方法，以及含有它们的制药组合物。还揭示了制备这些化合物的方法。
• THYRONAMINE DERIVATIVES AND ANALOGS AND METHODS OF USE THEREOF
  申请人：Scanlan Thomas S.

  公开号：US20090105347A1

  公开（公告）日：2009-04-23

  Thyronamine derivatives and analogs, methods of using such compounds, and pharmaceutical compositions containing them are disclosed. Methods of preparing such compounds are also disclosed

  本发明涉及甲状腺胺衍生物和类似物，使用这些化合物的方法以及包含它们的药物组合物。本发明还揭示了制备这些化合物的方法。
• Naphthyl acetamides as sPLA2 inhibitors
  申请人：ELI LILLY AND COMPANY

  公开号：EP0779271A1

  公开（公告）日：1997-06-18

  A class of novel naphthyl acetamide compounds of formula (I) is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of conditions such as septic shock.

  本研究公开了一类新颖的式 (I) 萘乙酰胺化合物，以及此类化合物用于抑制 sPLA2 介导的脂肪酸释放以治疗脓毒性休克等疾病的用途。
• [EN] NAPHTHYL ACETAMIDES AS sPLA2 INHIBITORS<br/>[FR] NAPHTYLE-ACETAMIDES UTILISES COMME INHIBITEURS DE sPLA2
  申请人：ELI LILLY AND COMPANY

  公开号：WO1997021664A1

  公开（公告）日：1997-06-19

  (EN) A class of novel naphthyl acetamide compounds is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of conditions such as septic shock.(FR) L'invention se rapporte à une classe de nouveaux composés naphtyle-acétamides ainsi qu'à leur utilisation dans l'inhibition de la libération d'acides gras induite par sPLA2 dans le traitement d'états tels que le choc septique.

  一种新型萘乙酰胺类化合物被披露，并且这些化合物用于抑制sPLA2介导的脂肪酸释放，以治疗如感染性休克等状况。本发明还涉及这类化合物在治疗此类状态中的应用，特别是通过抑制sPLA2介导的脂肪酸释放。