(R)-N-[1-(4-Carbamimidoyl-benzyl)-2-oxo-2-piperidin-1-yl-ethyl]-3-mercapto-2-(naphthalene-2-sulfonylamino)-propionamide | 774524-52-6

• 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: (R)-N-[1-(4-Carbamimidoyl-benzyl)-2-oxo-2-piperidin-1-yl-ethyl]-3-mercapto-2-(naphthalene-2-sulfonylamino)-propionamide
• CAS: 774524-52-6
• 化学式: C₂₈H₃₃N₅O₄S₂
• 分子量: 567.733
• InChiKey: ARLREWMTYHAEJA-BBMPLOMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  145.45
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-N-[1-(4-Carbamimidoyl-benzyl)-2-oxo-2-piperidin-1-yl-ethyl]-3-mercapto-2-(naphthalene-2-sulfonylamino)-propionamide 、 (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[(2R,3S,4S,5R,6R)-2-carboxy-4-methoxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-5-sulfooxyoxan-3-yl]oxy-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-3-[(2R,3R,4S,5R,6R)-5-[2-[2-[2-[2-[[4-[(2-iodoacetyl)amino]benzoyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]-3,4-disulfooxy-6-(sulfooxymethyl)oxan-2-yl]oxy-4-methoxy-5-sulfooxyoxane-2-carboxylic acid 在 0.1 M aq. NaHPO₃ (pH 7.0) 作用下， 反应 3.0h， 生成 (2S,3S,4S,5R,6R)-3-[(2R,3R,4S,5R,6R)-5-[2-[2-[2-[2-[[4-[[2-[(2R)-3-[[3-(4-carbamimidoylphenyl)-1-oxo-1-piperidin-1-ylpropan-2-yl]amino]-2-(naphthalen-2-ylsulfonylamino)-3-oxopropyl]sulfanylacetyl]amino]benzoyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]-3,4-disulfooxy-6-(sulfooxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4S,5R,6R)-6-[(2R,3S,4S,5R,6R)-2-carboxy-4-methoxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-5-sulfooxyoxan-3-yl]oxy-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-4-methoxy-5-sulfooxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of a novel synthetic NAPAP-penta-saccharide conjugate displaying a dual antithrombotic action

  摘要：

  The synthesis of a novel antithrombotic consisting of a heparin pentasaccharide conjugated to the active site inhibitor N-(2-naphtalenesulfonyl)-glycyl-(D)-4-aminophenyl-alanyl-piperidine(NAPAP) (i.e. compound I) is reported. This conjugate shows a unique pharmacological profile both in vitro and in vivo having direct anti-thrombin and ATIII-mediated anti-Xa activity. Furthermore, conjugate I has a prolonged in vivo half-life compared to NAPAP (1.5 h vs 9 min.), (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00320-0
• 作为产物：
  描述：

  N-2-Naphtalenesulfonyl-S-4-monomethoxytrityl-(L)-cysteine 在 N-乙基吗啉 、 三异丙基硅烷 、 三丁基膦 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 18.33h， 生成 (R)-N-[1-(4-Carbamimidoyl-benzyl)-2-oxo-2-piperidin-1-yl-ethyl]-3-mercapto-2-(naphthalene-2-sulfonylamino)-propionamide
  参考文献：
  名称：

  Design and synthesis of a novel synthetic NAPAP-penta-saccharide conjugate displaying a dual antithrombotic action

  摘要：

  The synthesis of a novel antithrombotic consisting of a heparin pentasaccharide conjugated to the active site inhibitor N-(2-naphtalenesulfonyl)-glycyl-(D)-4-aminophenyl-alanyl-piperidine(NAPAP) (i.e. compound I) is reported. This conjugate shows a unique pharmacological profile both in vitro and in vivo having direct anti-thrombin and ATIII-mediated anti-Xa activity. Furthermore, conjugate I has a prolonged in vivo half-life compared to NAPAP (1.5 h vs 9 min.), (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00320-0