苄氧羰基-酪氨酰-亮氨酸 | 35971-70-1

• 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
• 中文名称: 苄氧羰基-酪氨酰-亮氨酸
• 英文名称: (S)-2-[(S)-2-benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl pentanoic acid
• 英文别名: (S)-2-[(S)-2-benzyloxycarbonylamino-3-(4-hydroxyphenyl)propionylamino]-4-methylpentanoic acid；Z-Tyr-Leu；N-(N-benzyloxycarbonyl-L-tyrosyl)-L-leucine；N-(N-Benzyloxycarbonyl-L-tyrosyl)-L-leucin；N-Benzyloxycarbonyl-L-tyrosly=>L-leucin；Z-Tyr-Leu-OH；(2S)-2-[[(2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoyl]amino]-4-methylpentanoic acid
• CAS: 35971-70-1
• 化学式: C₂₃H₂₈N₂O₆
• mdl: MFCD00038300
• 分子量: 428.485
• InChiKey: SZUJNVXDTHBDRE-PMACEKPBSA-N

物化性质

• 熔点：
  72-74 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  724.4±60.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.347
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苄氧羰基-酪氨酰-亮氨酸 在 palladium on activated charcoal 吡啶 、 盐酸 、 聚合甲醛 、 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.75h， 生成 Ac-YLR-CHO
  参考文献：
  名称：

  Inhibition studies of some serine and thiol proteinases by new leupeptin analogs

  摘要：

  Fifteen tripeptide analogues of leupeptin containing either a C-terminal argininal or lysinal were synthesized. The synthetic analogues were tested, using spectrophotometric assay techniques, as inhibitors of trypsin, kallikrein, thrombin, plasmin, and cathepsin B. The lysinal analogues were fairly selective as inhibitors of cathepsin B activity, Acetyl-L-leucyl-L-valyl-L-lysinal (21) showed a stronger inhibition of cathepsin B (IC50 = 4 nanomolar) than leupeptin. Acetyl-L-phenylalanyl-L-valyl-L-argininal (2i) was found to be a good inhibitor of cathepsin B (IC50 = 0.039 muM), thrombin (IC50 = 1.8 muM), and plasmin (IC50 = 2.2 muM).

  DOI：

  10.1021/jm00060a016
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 苄氧羰基-酪氨酰-亮氨酸
  参考文献：
  名称：

  Zahn; Messerknecht, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1959, vol. 315, p. 228,230

  摘要：

  DOI：

文献信息

• Efficient Large-Scale Synthesis of CAT811, a Potent Calpain Inhibitor of Interest in the Treatment of Cataracts
  作者：Matthew A. Jones、James M. Coxon、Stephen B. McNabb、Janna M. Mehrtens、Nathan A. Alexander、Seth Jones、Hongyuan Chen、Clémence Buisan、Andrew D. Abell

  DOI：10.1071/ch09101

  日期：——

  A high-yielding, short, and scalable synthesis of a potent calpain 2 inhibitor (CAT811) is reported. The key step in the sequence involves an intramolecular macrocyclization of a 6-iodonorleucine residue to the side chain of tyrosine.

  报告了一种高产、简短、可扩展的强效钙蛋白酶 2 抑制剂（CAT811）的合成方法。该过程的关键步骤是将 6-碘亮氨酸残基与酪氨酸侧链进行分子内大环化。
• Macrocyclic cysteine protease inhibitors and compositions thereof
  申请人：Lincoln University

  公开号：US09434762B2

  公开（公告）日：2016-09-06

  The present invention provides a novel class of macrocyclic compounds, which are useful as cysteine protease inhibitors. Also provided are novel intermediates and methods of preparing the compounds. The invention also provides pharmaceutical compositions comprising the compounds. The compounds and compositions are useful in methods of treating or preventing one or more diseases associated with cysteine protease activity, particularly those associated with calpain activity.

  本发明提供了一类新型的大环化合物，这些化合物可用作半胱氨酸蛋白酶抑制剂。还提供了新颖的中间体和制备这些化合物的方法。该发明还提供了包含这些化合物的药物组合物。这些化合物和组合物可用于治疗或预防与半胱氨酸蛋白酶活性相关的一种或多种疾病，特别是与钙蛋白酶活性相关的疾病。
• Macrocyclic Cysteine Protease Inhibitors and Compositions Thereof
  申请人：Abell Andrew David

  公开号：US20110021434A1

  公开（公告）日：2011-01-27

  The present invention provides a novel class of macrocyclic compounds, which are useful as cysteine protease inhibitors. Also provided are novel intermediates and methods of preparing the compounds. The invention also provides pharmaceutical compositions comprising the compounds. The compounds and compositions are useful in methods of treating or preventing one or more diseases associated with cysteine protease activity, particularly those associated with calpain activity.

  本发明提供了一类新型的大环化合物，可用作半胱氨酸蛋白酶抑制剂。还提供了新型中间体和制备这些化合物的方法。该发明还提供了包含这些化合物的药物组合物。这些化合物和组合物可用于治疗或预防与半胱氨酸蛋白酶活性有关的一种或多种疾病，特别是与钙蛋白酶活性有关的疾病。
• Zahn,H.; La France,N.H., Justus Liebigs Annalen der Chemie, 1960, vol. 630, p. 37 - 46
  作者：Zahn,H.、La France,N.H.

  DOI：——

  日期：——
• US8710178B2
  申请人：——

  公开号：US8710178B2

  公开（公告）日：2014-04-29