(S)-5-Bromo-3-{(S)-3-methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-pentanoic acid tert-butyl ester | 265119-58-2

• 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: (S)-5-Bromo-3-{(S)-3-methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-pentanoic acid tert-butyl ester
• 英文别名: tert-butyl (3S)-5-bromo-3-[[(2S)-3-methyl-2-[(2-naphthalen-1-yloxyacetyl)amino]butanoyl]amino]-4-oxopentanoate
• CAS: 265119-58-2
• 化学式: C₂₆H₃₃BrN₂O₆
• 分子量: 549.462
• InChiKey: PEKOGSNRKICMOM-CYFREDJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (S)-5-Bromo-3-{(S)-3-methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-pentanoic acid tert-butyl ester 在 potassium fluoride 、 苯甲醚 、 三氟乙酸 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-5-(4,6-Dimethyl-pyrimidin-2-yloxy)-3-{(S)-3-methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-pentanoic acid
  参考文献：
  名称：

  Structure–activity relationships within a series of caspase inhibitors. Part 2: Heterocyclic warheads

  摘要：

  Various heterocyclic hetero-methyl ketones of the 1-naphthyloxyacetyl-Val-Asp backbone have been prepared. A study of their structure-activity relationship (SAR) related to caspase-1, -3, -6, and -8 is reported. Their efficacy in a cellular model of cell death is also discussed. Potent broad-spectrum caspase inhibitors have been identified. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.036
• 作为产物：
  描述：

  1-萘氧基乙酸 在 N-甲基吗啉 、 lithium hydroxide 、 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 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (S)-5-Bromo-3-{(S)-3-methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  Structure–Activity relationships within a series of caspase inhibitors: effect of leaving group modifications

  摘要：

  Various aryloxy methyl ketones of the 1-naphthyloxyacetyl-Val-Asp backbone have been prepared. A systematic study of their structure-activity relationship (SAR) related to caspases 1, 3, 6, and 8 is reported. Highly potent irreversible broad-spectrum caspase inhibitors have been identified. Their efficacy in cellular models of cell death and inflammation are also discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00755-8

文献信息

• [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：——

  公开号：US20020091089A1

  公开（公告）日：2002-07-11

  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，以及保护即将进行移植手术的器官的用途。
• (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