Cbz-L-Val-L-propinal | 91650-00-9

• 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: Cbz-L-Val-L-propinal
• 英文别名: Z-L-Val-L-prolinal；N-Benzyloxycarbonylvalylprolinal；benzyl N-[(2S)-1-[(2S)-2-formylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 91650-00-9
• 化学式: C₁₈H₂₄N₂O₄
• 分子量: 332.4
• InChiKey: QRONLDFFPZYHDZ-HOTGVXAUSA-N

物化性质

• 沸点：
  528.9±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Cbz-L-Val-L-propinal 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.5h， 生成 {(S)-3-[(S)-1-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-ylmethyl]-4-isobutyl-5-oxo-imidazolidin-1-yl}-acetic acid methyl ester
  参考文献：
  名称：

  Noncovalent inhibitors of human leukocyte elastase based on the 4-imidazolidinone scaffold

  摘要：

  A central problem associated with the design of enzyme inhibitors in general, and serine protease inhibitors in particular, is the identification of templates capable of binding to the active site of an enzyme in a predictable and substrate-like fashion, orienting appended recognition elements in a correct spatial relationship so that favorable binding interactions with multiple sites are achieved. Described herein for the first time is the design of noncovalent inhibitors of human leukocyte elastase that employs a functionalized 4-imidazolidinone scaffold. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.030
• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 在 palladium on activated charcoal 盐酸 、 聚合甲醛 、 氢气 、 sodium acetate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.12h， 生成 Cbz-L-Val-L-propinal
  参考文献：
  名称：

  Synthesis and structure of prolinal-containing peptides, and their use as specific inhibitors of prolyl endopeptidases.

  摘要：

  肽醛是丝氨酸和半胱氨酸蛋白酶的强效抑制剂。在本研究工作中，合成了含羧基末端脯氨醛的N-苄氧羰基（Z）二肽，作为脯氨酰内肽酶的抑制剂。由于通过质子核磁共振（1H-NMR）光谱法未检测到醛质子，因此为这些肽提出了一个环状结构。具有Z-L-X-L-脯氨醛结构的化合物是海鞘Halocynthia roretzi和黄杆菌Flavobacterium meningosepticum的脯氨酰内肽酶的强效抑制剂。其效力顺序为Z-L-Val-L-脯氨醛≈Z-L-Ile-L-脯氨醛>Z-L-Phe-L-脯氨醛>Z-L-Ala-L-脯氨醛，IC50值为10-8-10-6 M，对两种酶均有效。将醛转化为醇或酸部分会导致抑制活性显著降低。Z-L-Phe-L-脯氨醛的差向异构体抑制作用较弱。这一结果与黄杆菌酶对其底物的报道立体特异性不一致。这表明开放型物种优先结合到酶活性位点。

  DOI：

  10.1248/cpb.34.2931

文献信息

• Anti-amnestic agent
  申请人：Kabushiki Kaisha Yakult Honsha

  公开号：US04687778A1

  公开（公告）日：1987-08-18

  An anti-amnestic agent which comprises as an active ingredient thereof at least one prolinal derivative of the general formula: ##STR1## wherein A is a protective groups for amino group in the field of amino acid chemistry and X is a residue of an amino acid, in a pharmacologically active amount together with an exipient. This agent is less toxic and can be safely administered to patients orally or intravenously for the remedy of memory disorder.

  一种抗遗忘剂，其活性成分至少包括一种普罗林酰衍生物，其通式如下：##STR1## 其中A是氨基酸化学领域中氨基保护基，X是氨基酸残基，与赋形剂一起以药理学有效量形式使用。该剂量毒性较小，可安全地口服或静脉注射给患者治疗记忆障碍。
• An anti-amnestic agent
  申请人：KABUSHIKI KAISHA YAKULT HONSHA

  公开号：EP0154353A2

  公开（公告）日：1985-09-11

  An anti-amnestic agent which comprises as an active ingredient thereof at least one prolinal derivative of the general formula I wherein A is a protective group for amino group in the field of amino acid chemistry and X is a residue of an amino acid, in a pharmacologically active amount together with an excipient. This agent is less toxic and can safely be administered to patients orally or intravenously for the remedy of memory disorder.

  一种抗失忆药剂，其有效成分包括至少一种通式 I 的脯氨酸衍生物，其中 A 是氨基酸化学领域中对氨基的保护基团，X 是氨基酸的残基，药效量与赋形剂一起使用。 这种药剂毒性较低，可安全地口服或静脉注射给患者，用于治疗记忆障碍。
• Design, synthesis, and in vitro evaluation of inhibitors of human leukocyte elastase based on a functionalized cyclic sulfamide scaffold
  作者：Jiaying Zhong、Xiangdong Gan、Kevin R Alliston、William C Groutas

  DOI：10.1016/j.bmc.2003.10.059

  日期：2004.2

  The design of novel functionalized templates capable of binding to the active site of serine proteases could potentially lead to the development of potent and highly selective non-covalent inhibitors of these enzymes. Using the elastase-turkey ovomucoid inhibitor complex and insights gained from earlier work based on the 1,2,5-thiadiazolidin-3-one 1,1 dioxide scaffold (I), a surrogate cyclosulfamide scaffold (II) was used for the first time in the design of reversible inhibitors of human leukocyte elastase. Compounds 7 and 8 were found to be micromolar reversible inhibitors of the enzyme. (C) 2003 Elsevier Ltd. All rights reserved.
• Dipeptide derivatives, processes for preparing them, pharmaceutical composition and use
  申请人：SUNTORY LIMITED

  公开号：EP0201741B1

  公开（公告）日：1991-07-31
• US4687778A
  申请人：——

  公开号：US4687778A

  公开（公告）日：1987-08-18