(R)-2-(Naphthalene-2-sulfonylamino)-3-(pyridin-2-yldisulfanyl)-propionic acid | 244606-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-(Naphthalene-2-sulfonylamino)-3-(pyridin-2-yldisulfanyl)-propionic acid
• 英文别名: (2R)-2-(naphthalen-2-ylsulfonylamino)-3-(pyridin-2-yldisulfanyl)propanoic acid
• CAS: 244606-17-5
• 化学式: C₁₈H₁₆N₂O₄S₃
• 分子量: 420.534
• InChiKey: HXFZLXXCFVSZAA-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-2-(Naphthalene-2-sulfonylamino)-3-(pyridin-2-yldisulfanyl)-propionic acid 在 N-乙基吗啉 、 三丁基膦 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 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
• 作为产物：
  描述：

  N-2-Naphtalenesulfonyl-S-4-monomethoxytrityl-(L)-cysteine 在 三异丙基硅烷 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 1.33h， 生成 (R)-2-(Naphthalene-2-sulfonylamino)-3-(pyridin-2-yldisulfanyl)-propionic 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

文献信息

• ANTITHROMBOTIC COMPOUNDS
  申请人：N.V. Organon

  公开号：EP1087992B1

  公开（公告）日：2008-08-20
• Design and synthesis of a novel synthetic NAPAP-penta-saccharide conjugate displaying a dual antithrombotic action
  作者：Rogier C. Buijsman、Jan E.M. Basten、Theo G. van Dinther、Gijsbert A. van der Marel、Constant A.A. van Boeckel、Jacques H. van Boom

  DOI：10.1016/s0960-894x(99)00320-0

  日期：1999.7

  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.