tert-butyl (3S)-3-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-4-oxobutanoate | 1246261-48-2

• 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: tert-butyl (3S)-3-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-4-oxobutanoate
• CAS: 1246261-48-2
• 化学式: C₂₁H₃₀N₂O₆
• 分子量: 406.479
• InChiKey: XQDKXPIUMVFYEV-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二乙基(甲基磺酰基)膦 、 tert-butyl (3S)-3-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-4-oxobutanoate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.0h， 以75%的产率得到Z-Val-Asp(β-tert-butyl)vinyl methylsulfone
  参考文献：
  名称：

  Synthesis and evaluation of vinyl sulfones as caspase-3 inhibitors. A structure–activity study

  摘要：

  The first structure activity relationship study of vinyl sulfones as caspase-3 inhibitors is reported. A series of 12 vinyl sulfones was synthesized and evaluated for two downstream caspases (caspases-3 and -7). Dipeptidyl derivatives were significantly superior to their counterparts containing only Asp at P(1), as caspase-3 inhibitors. Fmoc-Val-Asp-trans-CH=CH-SO(2)Me was the most potent inhibitor of caspase-3 in the series, with a IC(50) of 29 mu M and a second-order rate constant of inactivation, k(inact)/(K)i, of 1.5 M(-1) s(-1) Computational studies suggest that the second amino acid occupies position S(3) of the enzyme. In addition, Fmoc-Val-Asp-trans-CH=CH-SO(2)Ph was inactive for caspase-7 for the tested concentrations. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.039

文献信息

• (Substituted)acyl dipeptidyl inhibitors of the ICE/ced-3 family of cysteine proteases
  申请人：Idun Pharmaceuticals, Inc.

  公开号：US20030232788A1

  公开（公告）日：2003-12-18

  This invention is directed to novel (substituted)acyl dipeptidyl ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as the use of such compositions in the treatment of patients suffering inflammatory, autoimmune and neurodegenerative diseases, for the prevention of ischemic injury, and for the preservation of organs that are to undergo a transplantation procedure.

  这项发明涉及新型（取代）酰基二肽酶ICE/ced-3家族抑制剂化合物。该发明还涉及含有这些化合物的药物组合物，以及将这些组合物用于治疗患有炎症、自身免疫和神经退行性疾病的患者，预防缺血性损伤，并保护即将进行移植手术的器官。
• [EN] (SUBSTITUTED)ACYL DIPEPTIDYL INHIBITORS OF THE ICE/ced-3 FAMILY OF CYSTEINE PROTEASES<br/>[FR] INHIBITEURS ACYLE(SUBSTITUE) DIPEPTIDYLE DE LA FAMILLE ICE/ced-3 DES CYSTEINES PROTEASES
  申请人：IDUN PHARMACEUTICALS INC

  公开号：WO2000023421A1

  公开（公告）日：2000-04-27

  This invention is directed to novel (substituted)acyl dipeptidyl ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as the use of such compositions in the treatment of patients suffering inflammatory, autoimmune and neurodegenerative diseases, for the prevention of ischemic injury, and for the preservation of organs that are to undergo a transplantation procedure.

  本发明涉及新型（取代）酰基二肽酶ICE / ced-3家族抑制剂化合物。本发明还涉及含有这些化合物的制药组合物，以及将这些组合物用于治疗患有炎症，自身免疫和神经退行性疾病的患者，预防缺血性损伤，并用于保护即将进行移植手术的器官。
• (Substituted)Acyl dipeptidyl inhibitors of the ICE/ced-3 family of cysteine proteases
  申请人：——

  公开号：US20040259804A1

  公开（公告）日：2004-12-23

  This invention is directed to novel (substituted) acyl dipeptidyl ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as the use of such compositions in the treatment of patients suffering inflammatory, autoimmune and neurodegenerative diseases, for the prevention of ischemic injury, and for the preservation of organs that are to undergo a transplantation procedure.

  本发明涉及新型（取代的）酰基二肽酰 ICE/ced-3 家族抑制剂化合物。本发明还涉及含有这些化合物的制药组合物，以及在治疗患有炎症、自身免疫和神经退行性疾病的患者、预防缺血性损伤以及保护即将进行移植手术的器官等方面使用这种组合物的用途。
• (SUBSTITUTED)ACYL DIPEPTIDYL INHIBITORS OF THE ICE/CED-3 FAMILY OF CYSTEINE PROTEASES
  申请人：Idun Pharmaceuticals, Inc.

  公开号：EP1123272A1

  公开（公告）日：2001-08-16
• US6242422B1
  申请人：——

  公开号：US6242422B1

  公开（公告）日：2001-06-05