Z-β-Ala-L-His-hydrazid | 17682-08-5

• 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: Z-β-Ala-L-His-hydrazid
• 英文别名: N^α-(N-benzyloxycarbonyl-β-alanyl)-histidine hydrazide；N^α-(N-benzyloxycarbonyl-β-alanyl)-L-histidine hydrazide；N^α-(N-Benzyloxycarbonyl-β-alanyl)-L-histidin-hydrazid；Histidine, N-(N-carboxy-I(2)-alanyl)-, N-benzyl ester, hydrazide, L-；benzyl N-[3-[[(2S)-1-hydrazinyl-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-oxopropyl]carbamate
• CAS: 17682-08-5
• 化学式: C₁₇H₂₂N₆O₄
• 分子量: 374.399
• InChiKey: HDBOOOLUIOQFER-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  151.23
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Z-β-Ala-L-His-hydrazid 在 盐酸 、 水 、 sodium nitrite 作用下， 生成 N-benzyloxycarbonyl-β-alanyl=>L-histidyl=>glycine ethyl ester
  参考文献：
  名称：

  Davis, Journal of Biological Chemistry, 1956, vol. 223, p. 935,945

  摘要：

  DOI：
• 作为产物：
  描述：

  N-CBZ-beta-丙氨酸 在 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 Z-β-Ala-L-His-hydrazid
  参考文献：
  名称：

  Neuroprotective effects of a novel carnosine-hydrazide derivative on hippocampal CA1 damage after transient cerebral ischemia

  摘要：

  Ischemia-reperfusion injuries produce reactive oxygen species that promote the peroxide lipid oxidation process resulting in the production of an endogenic lipid peroxide, 4-hydroxy-trans-2-nonenal (4-HNE), a highly cytotoxic aldehyde that induces cell death. We synthesized a novel 4-HNE scavenger a carnosine-hydrazide derivative, L-carnosine hydrazide (CNN) - and examined its neuroprotective effect in a model of transient ischemia.PC-12 cells were pre-incubated with various doses (0-50 mmol/L) of CNN for 30 min, followed by incubation with 4-HNE (250 mu M). An MIT assay was performed 24 h later to examine cell survival. Transient ischemia was induced by bilateral common carotid artery occlusion (BCCO) in the Mongolian gerbil. Animals were assigned to sham-operated (n = 6), placebo-treated (n = 12), CNN pre-treated (20 mg/kg; n = 12), CNN post-treated (100 mg/kg; n = 11), and histidyl hydrazide (a previously known 4-HNE scavenger) post-treated (100 mg/kg; n = 7) groups. Heat shock protein 70 immunoreactivity in the hippocampal CM region was evaluated 24 h later, while delayed neuronal death using 4-HNE staining was evaluated 7 days later.Pre-incubation with 30 mmol/L CNN completely inhibited 4-HNE-induced cell toxicity. CNN prevented delayed neuronal death by >60% in the pre-treated group (p < 0.001) and by >40% in the post-treated group (p <0.01). Histidyl hydrazide post-treatment elicited no protective effect. CNN pre-treatment resulted in high heat shock protein 70 and low 4-HNE immunoreactivity in CAl pyramidal neurons. Higher 4-HNE immunoreactivity was also found in the placebo-treated animals than in the CNN pretreated animals.Our novel compound, CNN, elicited highly effective 4-HNE scavenging activity in vitro. Furthermore, CNN administration both pre- and post-BCCO remarkably reduced delayed neuronal death in the hippocampal CAl region via its induction of heat shock protein 70 and scavenging of 4-HNE. (C) 2018 The Authors. Published by Elsevier Masson SAS. This is an open access article under the CC BY-NC-ND license.

  DOI：

  10.1016/j.ejmech.2018.11.060