2-ethoxy-8-isothiocyanato-1,4-dihydronaphthalene | 914090-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-ethoxy-8-isothiocyanato-1,4-dihydronaphthalene
• 英文别名: 2-Ethoxy-8-isothiocyanato-1,4-dihydronaphthalene
• CAS: 914090-84-9
• 化学式: C₁₃H₁₃NOS
• 分子量: 231.318
• InChiKey: WZGKBBSWOQJBTB-UHFFFAOYSA-N

物化性质

• 沸点：
  404.1±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  53.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethoxy-8-isothiocyanato-1,4-dihydronaphthalene 、 2-azido-4'-chloroacetophenone 在 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 5-(4-chlorophenyl)-N-(7-ethoxy-5,8-dihydronaphthalen-1-yl)-1,3-oxazol-2-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-substituted and 4,5-disubstituted-2-arylamino oxazole TRPV1 antagonists

  摘要：

  The synthesis and structure-activity relationships of a series of 5-monosubstituted and 4,5-disubstituted 2-arylaminooxazoles as novel antagonists of the transient receptor potential vanilloid 1 (TRPV1) receptor are described. The 7-hydroxy group of the tetrahydronaphthyl moiety on the 2-amino substituent of the oxazole ring was important for obtaining excellent in vitro potency at the human TRPV1 receptor, while a variety of alkyl and phenyl substituents at the 4- and 5-positions of the oxazole ring were well tolerated and yielded potent TRPV1 antagonists. Despite excellent in vitro potency, the 5-monosubstituted compounds suffered from poor pharmacokinetics. It was found that 4,5-disubstitution on the oxazole ring was critical to the improvement of the overall pharmacokinetic profile of these analogues, which led to the discovery of compound (R)-27, a novel TRPV1 antagonist with good oral activity in preclinical animal models of pain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.099
• 作为产物：
  描述：

  7-乙氧基-5,8-二氢萘-1-胺 、 二吡啶硫碳酸酯 在 silica gel 、 ethyl acetate n-hexane 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以afforded the title compound as a pale pink solid, 225 mg (92%)的产率得到2-ethoxy-8-isothiocyanato-1,4-dihydronaphthalene
  参考文献：
  名称：

  Antagonists of the vanilloid receptor subtype 1 (VR1) and use thereof

  摘要：

  本发明涉及式(I)化合物，其中变量W、X、Y、D、A、n、R1、R2和R9如描述中所定义。

  公开号：

  US07902236B2

文献信息

• Antagonists of the vanilloid receptor subtype 1 (VR1) and use thereof
  申请人：Gomtsyan Arthur

  公开号：US20060281799A1

  公开（公告）日：2006-12-14

  The present invention is directed to compounds of formula (I) wherein variables W, X, Y, D, A, n, R 1 , R 2 and R 9 are as defined in the description.

  本发明涉及式(I)的化合物，其中变量W、X、Y、D、A、n、R1、R2和R9如描述中所定义。
• ANTAGONISTS OF THE VANILLOID RECEPTOR SUBTYPE 1 (VR1) AND USE THEREOF
  申请人：Gomtsyan Arthur

  公开号：US20100010055A1

  公开（公告）日：2010-01-14

  The present invention is directed to compounds of formula (I) wherein variables W, X, Y, D, A, n, R 1 , R 2 and R 9 are as defined in the description.

  本发明涉及式（I）的化合物，其中变量W，X，Y，D，A，n，R1，R2和R9如描述中所定义。
• WO2006/122250
  申请人：——

  公开号：——

  公开（公告）日：——
• ANTAGONISTS OF THE VANILLOID RECEPTOR SUBTYPE 1 (VR1) AND USES THEREOF
  申请人：ABBOTT LABORATORIES

  公开号：EP1885704A2

  公开（公告）日：2008-02-13
• US7504520B2
  申请人：——

  公开号：US7504520B2

  公开（公告）日：2009-03-17