tert-butyl 5-(acetylthio)-4(S)-(tert-butoxycarbonylamino)pentanoate | 156143-30-5

• 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: tert-butyl 5-(acetylthio)-4(S)-(tert-butoxycarbonylamino)pentanoate
• 英文别名: tert-butyl (4S)-5-acetylsulfanyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 156143-30-5
• 化学式: C₁₆H₂₉NO₅S
• 分子量: 347.476
• InChiKey: JMYLHVFUQSQNKY-LBPRGKRZSA-N

物化性质

• 熔点：
  50-52 °C
• 沸点：
  443.4±40.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-(acetylthio)-4(S)-(tert-butoxycarbonylamino)pentanoate 在 盐酸 、 sodium hydroxide 、 phosphate buffer 作用下， 以 甲醇 为溶剂， 反应 84.0h， 生成 3-[(4S)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]propanoic acid
  参考文献：
  名称：

  Desazadesmethyldesferrithiocin Analogues as Orally Effective Iron Chelators

  摘要：

  Further structure-activity studies of desferrithiocin analogues are carried out. (S)-desazadesmethyldesferrithiocin, 2-(2-hydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid, serves as the principal framework in the current paper. Desazadesmethyldesferrithiocin can be structurally altered with facility, and data are already available on its iron-clearing properties and toxicity parameters. Four different kinds of structural modifications of this framework are undertaken: introduction of hydroxy, carboxy, or methoxy groups on the aromatic ring; alteration of the thiazoline ring; increasing the distance between the ligand donor atoms; and benz-fusion of the aromatic rings. The structural modifications described are shown to have a tremendous imp act on both the iron clearance and toxicity profiles of the desazadesmethyldesferrithiocin molecule. All of the compounds are assessed in a bile-duct-cannulated rodent model to determine iron clearance efficiency. Ligands which demonstrate an efficiency of greater than 2% are carried forward to the iron-overloaded primate for iron-clearing measurements. Ligands with efficiencies greater than 3% in the primate are then evaluated in a formal toxicity study in rodents. On the basis of the results of the present work, 2-(2,4-dihydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid is a promising candidate for clinical evaluation.

  DOI：

  10.1021/jm980340j
• 作为产物：
  描述：

  tert-butyl 4(S)-(tert-butoxycarbonylamino)-5-hydroxypentanoate 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 tert-butyl 5-(acetylthio)-4(S)-(tert-butoxycarbonylamino)pentanoate
  参考文献：
  名称：

  [EN] NOVEL FLUORESCENT DYES AND USES THEREOF
  [FR] NOUVEAUX COLORANTS FLUORESCENTS ET LEURS UTILISATIONS

  摘要：

  本发明提供基于萤火虫荧光素结构的荧光染料。这些染料在较短波长下被最佳激发，并具有至少50纳米的斯托克斯位移。本发明的荧光染料可用于制备染料偶联物，该偶联物可用于检测样品中的分析物。

  公开号：

  WO2011008912A1

文献信息

• Investigation of the Active Site of Aminopeptidase A Using a Series of New Thiol-Containing Inhibitors
  作者：Eric N. Chauvel、Pascale Coric、Catherine Llorens-Cortes、Sherwin Wilk、Bernard P. Roques、Marie-Claude Fournie-Zaluski

  DOI：10.1021/jm00035a014

  日期：1994.4

  Aminopeptidase A (APA) and aminopeptidase N (APN) are two metallopeptidases which have been suggested to be involved in the enzymatic cascade of the renin-angiotensin system. APA liberates angotensin III from angiotensin II by releasing the N-terminal aspartate, and APN participates in the inactivation of angiotensin III. As the role of angiotensin III in the regulation of blood pressure in the central nervous system and at the periphery is controversial, it was of interest to develop selective and efficient inhibitors of APA. Starting from Glu-thiol,(1) which was the first efficient APA inhibitor described, but however is equipotent on APA (K-i = 0.14 mu M) and APN (K-i = 0.12 mu M), beta-amino thiols bearing various carboxyalkyl chains have been synthesized and their inhibitory potencies measured on both purified enzymes. Compounds containing a carboxylated aromatic ring inhibited APA and APN with K-i values in the micromolar range but were slightly more active on APA. Conversely, inhibitors containing a cyclohexyl ring were more efficient on APN. Various modifications of the structure of Glu-thiol decreased inhibitory activity on both enzymes but increased the selectivity for APA, and compound 9d ((S)-4-amino-6-mercaptohexanoic acid) was 23 times more potent on APA (K-i = 2.0 mu M) than on APN (K-i = 45 mu M).