4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester | 168050-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl 4-[2-[[(2S)-1-[(2S)-2-(naphthalen-2-ylsulfonylamino)-3-phenylmethoxypropanoyl]pyrrolidin-2-yl]methylamino]-2-oxoethyl]piperidine-1-carboxylate
• CAS: 168050-53-1
• 化学式: C₄₀H₄₆N₄O₇S
• 分子量: 726.894
• InChiKey: FFROIGOORHUDPC-JSXFGMRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester 在 palladium on activated charcoal 乙醇 、 氢气 、 乙酰氯 作用下， 生成 N-{(S)-1-[(S)-3-Hydroxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-2-piperidin-4-yl-acetamide
  参考文献：
  名称：

  Thrombin active site inhibitors: chemical synthesis, in vitro and in vivo pharmacological profile of a novel and selective agent BMS-189090 and analogues

  摘要：

  A series of structurally novel small molecule inhibitors of human alpha -thrombin was prepared to elucidate their structure-activity relationships (SAR), selectivity and activity in vivo. BMS-189090 (5) is identified as a potent, selective, and reversible inhibitor of human alpha -thrombin that is efficacious in vivo in a mice lethality model, and in inhibiting both arterial and venous thrombosis in a rat model. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00664-3
• 作为产物：
  描述：

  [(S)-2-((S)-2-Azidomethyl-pyrrolidin-1-yl)-1-benzyloxymethyl-2-oxo-ethyl]-carbamic acid tert-butyl ester 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Thrombin active site inhibitors: chemical synthesis, in vitro and in vivo pharmacological profile of a novel and selective agent BMS-189090 and analogues

  摘要：

  A series of structurally novel small molecule inhibitors of human alpha -thrombin was prepared to elucidate their structure-activity relationships (SAR), selectivity and activity in vivo. BMS-189090 (5) is identified as a potent, selective, and reversible inhibitor of human alpha -thrombin that is efficacious in vivo in a mice lethality model, and in inhibiting both arterial and venous thrombosis in a rat model. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00664-3

文献信息

• N-acylpyrrolidines or N-acylpiperidines having a guanidinyl- or amidinyl-substituted side chain as thrombin inhibitors
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0623596A1

  公开（公告）日：1994-11-09

  Guanidinyl- or amidinyl-substituted heterocyclic thrombin inhibitors are provided which have the structure wherein n is 0, 1 or 2;    R¹ is -A-R², -CO-A-R² or -SO₂-A-R²; wherein R² is guanidine, amidine or amino, and A is an alkyl, alkenyl or alkynyl chain of 2 to 6 carbons; or    R¹ is -(CH₂)p-A'-R2' or -(CH₂)p-CO-A'R2' where p is 0, 1 or 2, R2' is amidine and A' is an azacycloalkyl or azaheteroalkyl ring of 4 to 8 atoms, optionally substituted by alkyl, CO or halo;    R¹ is -(CH₂)p-A''-R2'', -(CH₂)p-CO-A''-R2'', or -(CH₂)p-SO₂-A''-R2'', wherein R2''is guanidine, amidine or aminomethyl, and A'' is aryl or cycloalkyl;    and R³, R⁴, R⁵ and R⁶ are as defined herein.

  提供了具有以下结构的胍基或脒基取代的杂环凝血酶抑制剂 其中 n 是 0、1 或 2； R¹为-A-R²、-CO-A-R²或-SO₂-A-R²； 其中 R² 是胍、脒或氨基，A 是 2 至 6 个碳原子的烷基、烯基或炔基链；或 R¹ 是-(CH₂)p-A'-R2'或-(CH₂)p-CO-A'R2'，其中 p 是 0、1 或 2，R2'是脒，A'是 4 至 8 个原子的偶氮环烷基或杂杂环烷基环，可选择被烷基、CO 或卤素取代； R¹ 是-(CH₂)p-A''-R2''、-(CH₂)p-CO-A''-R2''或-(CH₂)p-SO₂-A''-R2''、 其中 R2''是胍基、脒基或氨甲基，A''是芳基或环烷基； 和 R³、R⁴、R⁵ 和 R⁶ 如本文所定义。
• US5583146A
  申请人：——

  公开号：US5583146A

  公开（公告）日：1996-12-10