Boc-γ-Gla[-Cys(SH)-Gly-OtBu]-OtBu | 918906-32-8

• 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: Boc-γ-Gla[-Cys(SH)-Gly-OtBu]-OtBu
• 英文别名: tert-butyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[[(2R)-1-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-1-oxo-3-sulfanylpropan-2-yl]carbamoylamino]propanoate
• CAS: 918906-32-8
• 化学式: C₂₂H₄₀N₄O₈S
• 分子量: 520.648
• InChiKey: ZUMQQHSJOCTJDP-KBPBESRZSA-N

物化性质

• 沸点：
  703.1±60.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  162
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Boc-γ-Gla[-Cys(SH)-Gly-OtBu]-OtBu 在 三异丙基硅烷 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 C₁₅H₂₄N₄O₁₀S
  参考文献：
  名称：

  Orally Bioavailable Prodrugs of ψ-GSH: A Potential Treatment for Alzheimer’s Disease

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c00779
• 作为产物：
  描述：

  N-(((S)-3-(tert-butoxy)-2-((tert-butoxycarbonyl)amino)-3-oxopropyl)carbamoyl)-S-trityl-L-cysteine 在 N-甲基吗啉 、 三异丙基硅烷 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 Boc-γ-Gla[-Cys(SH)-Gly-OtBu]-OtBu
  参考文献：
  名称：

  Orally Bioavailable Prodrugs of ψ-GSH: A Potential Treatment for Alzheimer’s Disease

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c00779

文献信息

• [EN] THERAPEUTIC COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS ET MÉTHODES THÉRAPEUTIQUES
  申请人：UNIV MINNESOTA

  公开号：WO2020010021A1

  公开（公告）日：2020-01-09

  Disclosed herein are compounds of formula I: (I) or pharmaceutically acceptable salts thereof, wherein R1, R2, and R3 may any of the values defined herein, as well as compositions comprising such compounds. Also disclosed are methods for treating diseases including neurodegenerative disorders such as Parkinson's Disease and Alzheimer's Disease.

  本文披露了以下式I的化合物：(I)或其药学上可接受的盐，其中R1、R2和R3可以是本文中定义的任何值，以及包含这种化合物的组合物。还披露了治疗疾病的方法，包括神经退行性疾病，如帕金森病和阿尔茨海默病。
• GLUTATHIONE ANALOGS AND USES THEREOF
  申请人：Vince Robert

  公开号：US20140154192A1

  公开（公告）日：2014-06-05

  The invention provides compounds of formula (I): (I) or salts thereof, wherein R1, R2, R3 Z, and X have any of the values defined herein, as well as compositions comprising such compounds. The compounds and compositions are useful for treating neurodegenerative disorders.

  本发明提供了式（I）的化合物或其盐，其中R1、R2、R3、Z和X具有本文所定义的任何值，以及包含这种化合物的组合物。这些化合物和组合物对于治疗神经退行性疾病是有用的。
• A metabolically stable tight-binding transition-state inhibitor of glyoxalase-I
  作者：Swati S. More、Robert Vince

  DOI：10.1016/j.bmcl.2006.08.121

  日期：2006.12

  The design, synthesis, and enzyme kinetics evaluation of a transition-state inhibitor of glyoxalase-I is described. The union of the hydroxamic acid zinc-chelator with a urea isostere for the glu-cys amide bond led to a glutathione analog which retained inhibitory potency toward glyoxalase-I while possessing resistance toward gamma-glutamyltranspeptidase mediated breakdown. This compound is viewed as a potential lead for the development of second-generation glyoxalase-I inhibitors wherein, the problems pertaining to metabolism and selectivity are overcome.
• Design, Synthesis and Biological Evaluation of Glutathione Peptidomimetics as Components of Anti-Parkinson Prodrugs
  作者：Swati S. More、Robert Vince

  DOI：10.1021/jm800239v

  日期：2008.8.1

  Plethoras of CNS-active drugs fail to effect their pharmacologic response due to their in vivo inability to cross the blood-brain barrier (BBB). The classical prodrug approach to overcome this frailty involves lipophilic derivatives of the polar drug, but we herein report a novel approach by which endogenous transporters at BBB are exploited for brain drug delivery. The crucial role played by glutathione in pathogenesis of Parkinson's and the presence of its influx transporters at the basolateral membrane of BBB served as the basis for our anti-Parkinson prodrug design strategy. A metabolically stable analogue of glutathione is used as a carrier for delivery of dopamine and adamantamine. An account of successful syntheses of these prodrugs along with their transport characteristics and stability determination is discussed.
• US9394338B2
  申请人：——

  公开号：US9394338B2

  公开（公告）日：2016-07-19