ethyl 3-(7-amidino-2-naphthyl)-2-{4-[(3S)-pyrrolidin-3-yloxy]phenyl}propanoate | 212139-24-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl 3-(7-amidino-2-naphthyl)-2-{4-[(3S)-pyrrolidin-3-yloxy]phenyl}propanoate
• 英文别名: 3-(7-Carbamimidoyl-naphthalen-2-yl)-2-[4-((S)-pyrrolidin-3-yloxy)-phenyl]-propionic acid ethyl ester；ethyl 3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-[(3S)-pyrrolidin-3-yl]oxyphenyl]propanoate
• CAS: 212139-24-7
• 化学式: C₂₆H₂₉N₃O₃
• 分子量: 431.535
• InChiKey: VZKCASWHKFZIEV-UXMRNZNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(7-amidino-2-naphthyl)-2-{4-[(3S)-pyrrolidin-3-yloxy]phenyl}propanoate 以76%的产率得到
  参考文献：
  名称：

  Nagahara Takayasu, Yokoyama Yukio, Inamura Kazue, Katakura Shin-ichi, Kom+, J. Med. Chem, 37 (1994) N 8, S 1200-1207

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[4-[[(3S)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy]phenyl]-3-(7-cyano-2-naphthyl)propionic acid ethyl ester 在 盐酸 、 乙醇 、 氨 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以56%的产率得到ethyl 3-(7-amidino-2-naphthyl)-2-{4-[(3S)-pyrrolidin-3-yloxy]phenyl}propanoate
  参考文献：
  名称：

  Design, synthesis and biological activity of amidinobicyclic compounds (derivatives of DX-9065a) as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Since factor Xa (fXa) plays a pivotal role in the blood coagulation cascade, inhibition of fXa is thought to be an effective treatment for a variety of thrombotic events. (2,)-2-[4-[[(3S)-l-Acetimidoyl-3-pyrrolidinyl]oxy]phenyl]-3-(7-amidino-2-naphthyl)propanoic acid hydrochloride pentahydrate (DX-9065a) was previously found in our laboratory as a novel orally active factor Xa inhibitor. DX-9065a exhibits a strong inhibitory activity toward fXa by occupying the substrate recognition (called SI) sites and aryl binding sites of fXa. Herein we describe conversions of the amidinonaphthalene and the acetimidoylpyrrolidine moieties of DX-9065a. Some compounds showed remarkably increased in vitro anti-factor Xa and PRCT activities compared with those of DX9065a. The most promising compound 38 showed four times the prolongation of APTT against DX-9065a after oral administration to rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.032