(3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester | 168319-04-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester
• 英文别名: Cbz-Val-Asp(OtBu)-CH2Br；tert-butyl (3S)-5-bromo-3-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-4-oxopentanoate
• CAS: 168319-04-8
• 化学式: C₂₂H₃₁BrN₂O₆
• 分子量: 499.402
• InChiKey: FBGXVLVCVFQQMJ-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成
  参考文献：
  名称：

  Oxamyl dipeptide caspase inhibitors developed for the treatment of stroke

  摘要：

  Structural modifications were made to a previously described acyl dipeptide caspase inhibitor, leading to the oxamyl dipeptide series. Subsequent SAR studies directed toward the warhead, P2, and P4 regions of this novel peptidomimetic are described herein. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.106
• 作为产物：
  描述：

  (S)-3-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-5-diazo-4-oxo-pentanoic acid tert-butyl ester 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 (3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester
  参考文献：
  名称：

  Dolle; Hoyer; Prasad, Journal of Medicinal Chemistry, 1994, vol. 37, # 5, p. 563 - 564

  摘要：

  DOI：

文献信息

• C-terminal modified oxamyl dipeptides as inhibitors of the ICE-ced-3 family of cysteine proteases
  申请人：——

  公开号：US20020042376A1

  公开（公告）日：2002-04-11

  This invention is directed to novel oxamyl dipeptide ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as to 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.

  这项发明涉及新型的oxamyl二肽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，以及在治疗患有炎症性、自身免疫和神经退行性疾病的患者中使用这些组合物，用于预防缺血性损伤，并用于保存即将进行移植手术的器官。
• C-terminal modified oxamyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases
  申请人：——

  公开号：US20020028774A1

  公开（公告）日：2002-03-07

  This invention is directed to novel oxamyl dipeptide ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as to 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.

  这项发明涉及新颖的oxamyl二肽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，并保护将要进行移植手术的器官。
• [EN] C-TERMINAL MODIFIED OXAMYL DIPEPTIDES AS INHIBITORS OF THE ICE/ced-3 FAMILY OF CYSTEINE PROTEASES<br/>[FR] OXAMYL DIPEPTIDES A TERMINAL C MODIFIE EN TANT QU'INHIBITEURS DE LA FAMILLE ICE/ced-3 DES PROTEASES DE CYSTEINE
  申请人：IDUN PHARMACEUTICALS INC

  公开号：WO2000001666A1

  公开（公告）日：2000-01-13

  This invention is directed to novel oxamyl depeptide ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as to 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.

  这项发明涉及新型的oxamyl depeptide 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中使用这些组合物的方法。
• Use of C-terminal modified oxamyl dipeptides as inhibitors of the ice/ced-3 family of cysteine proteases
  申请人：Idun Pharmaceuticals, Inc.

  公开号：EP1754475A1

  公开（公告）日：2007-02-21

  The present invention relates to the use of compounds for formula (I), wherein R1, A, B and R2 are defined herein, for the manufacture of a medicament for the treatment of an infectious disease or an inflammatory condition or for prolonging organ viability for use in transplantation.

  本发明涉及式(I)化合物的用途，其中 R1、A、B 和 R2 在本文中定义，用于制造治疗传染性疾病或炎症的药物，或用于延长移植手术中器官的存活时间。
• α-((Tetronoyl)oxy)- and α-((tetramoyl)oxy)methyl ketone inhibitors of the interleukin-1β converting enzyme (ICE)
  作者：Todd L. Graybill、Catherine P. Prouty、Gary J. Speier、Denton Hoyer、Roland E. Dolle、Carla T. Helaszek、Mark A. Ator、Joanne Uhl、Joost Strastes

  DOI：10.1016/s0960-894x(96)00574-4

  日期：1997.1

  Aryl-substituted tetronic acids, tetramic acids, and cyclic beta-dicarbonyl moieties were evaluated as leaving groups in the peptidyl-COCH2-X type inhibitor iii. Tripeptidyl aspartyl alpha-((tetronoyl)oxy)- and alpha-((tetramoyl)oxy)methyl ketone derivatives demonstrate potent time-dependent inhibition (k(obs)/[T] 100,000-250,000 M(-1)s(-1)) of the cysteine protease ICE. Copyright (C) 1996 Elsevier Science Ltd