(S)-3-{[3-(1-{Benzyloxycarbonylamino-[(Z)-benzyloxycarbonylimino]-methyl}-piperidin-4-ylmethoxy)-isoxazole-5-carbonyl]-amino}-2-butoxycarbonylamino-propionic acid methyl ester | 169605-45-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-{[3-(1-{Benzyloxycarbonylamino-[(Z)-benzyloxycarbonylimino]-methyl}-piperidin-4-ylmethoxy)-isoxazole-5-carbonyl]-amino}-2-butoxycarbonylamino-propionic acid methyl ester
• CAS: 169605-45-2
• 化学式: C₃₆H₄₄N₆O₁₁
• 分子量: 736.779
• InChiKey: YSZSQOJBMSLGTM-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  53.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  209.22
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 (S)-3-{[3-(1-{Benzyloxycarbonylamino-[(Z)-benzyloxycarbonylimino]-methyl}-piperidin-4-ylmethoxy)-isoxazole-5-carbonyl]-amino}-2-butoxycarbonylamino-propionic acid methyl ester 以75%的产率得到(S)-2-Butoxycarbonylamino-3-{[3-(1-carbamimidoyl-piperidin-4-ylmethoxy)-isoxazole-5-carbonyl]-amino}-propionic acid methyl ester; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists

  摘要：

  Despite the excellent in vitro potency of a series of benzamide glycoprotein IIb/IIIa antagonists, which have been reported previously, poor in vivo potency in the inhibition of platelet aggregation was observed when the most potent inhibitor XU057 was dosed intravenously to dogs. In this communication, we report that replacement of the benzamide in XU057 with an isoxazolecarboxamide resulted in significant improvement in in vivo potency. More importantly, the analogue XU065 showed an excellent oral antiplatelet effect in dogs. (C) 1998 The DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00637-4
• 作为产物：
  描述：

  N-Boc-4-哌啶甲醇 在 盐酸 、 4-二甲氨基吡啶 、 lithium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-3-{[3-(1-{Benzyloxycarbonylamino-[(Z)-benzyloxycarbonylimino]-methyl}-piperidin-4-ylmethoxy)-isoxazole-5-carbonyl]-amino}-2-butoxycarbonylamino-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists

  摘要：

  Despite the excellent in vitro potency of a series of benzamide glycoprotein IIb/IIIa antagonists, which have been reported previously, poor in vivo potency in the inhibition of platelet aggregation was observed when the most potent inhibitor XU057 was dosed intravenously to dogs. In this communication, we report that replacement of the benzamide in XU057 with an isoxazolecarboxamide resulted in significant improvement in in vivo potency. More importantly, the analogue XU065 showed an excellent oral antiplatelet effect in dogs. (C) 1998 The DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00637-4