[(6RS)-6-[2-[4-[[(3S)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy]phenyl]ethyl]-5,6,7,8-tetrahydro-2-naphthyl]carboxamide | 859140-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: [(6RS)-6-[2-[4-[[(3S)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy]phenyl]ethyl]-5,6,7,8-tetrahydro-2-naphthyl]carboxamide
• CAS: 859140-18-4
• 化学式: C₂₈H₃₆N₂O₄
• 分子量: 464.605
• InChiKey: ARGLTYULCJMSOO-KUXBLMNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.86
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(6RS)-6-[2-[4-[[(3S)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy]phenyl]ethyl]-5,6,7,8-tetrahydro-2-naphthyl]carboxamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以73%的产率得到[(6RS)-6-[2-[4-[[(3S)-3-pyrrolidinyl]oxy]phenyl]ethyl]-5,6,7,8-tetrahydro-2-naphthyl]carboxamide
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006
• 作为产物：
  描述：

  [(6RS)-6-[2-[4-[[(3S)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy]phenyl]ethyl]-5,6,7,8-tetrahydro-2-naphthyl]carboxylic acid 在 ammonium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.25h， 生成 [(6RS)-6-[2-[4-[[(3S)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy]phenyl]ethyl]-5,6,7,8-tetrahydro-2-naphthyl]carboxamide
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006