N-Benzyloxycarbonyl-D,L-homocystein-thiolacton | 38869-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Benzyloxycarbonyl-D,L-homocystein-thiolacton
• 英文别名: benzyl N-(2-oxothiolan-3-yl)carbamate
• CAS: 38869-96-4
• 化学式: C₁₂H₁₃NO₃S
• mdl: MFCD11046500
• 分子量: 251.306
• InChiKey: XGFIYNWPCHLLAP-UHFFFAOYSA-N

物化性质

• 沸点：
  466.4±44.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Benzyloxycarbonyl-D,L-homocystein-thiolacton 在 N-甲基吗啉 、 氢氧化钾 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.5h， 生成 methyl (2S)-2-[[(2S)-4-acetylsulfanyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-6-hydroxyhexanoate
  参考文献：
  名称：

  Dual Metalloprotease Inhibitors:  Mercaptoacetyl-Based Fused Heterocyclic Dipeptide Mimetics as Inhibitors of Angiotensin-Converting Enzyme and Neutral Endopeptidase

  摘要：

  A series of 7,6- and 7,5-fused bicyclic thiazepinones and oxazepinones were generated and incorporated as conformationally restricted dipeptide surrogates in mercaptoacyl dipeptides. These compounds are potent inhibitors of angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP) both in vitro and in vivo. Compound 1a, a 7,6-fused bicyclic thiazepinone, demonstrated excellent blood pressure lowering in a variety of animal models characterized by various levels of plasma renin activity and significantly potentiated urinary sodium, ANP, and cGMP excretion in a cynomolgus monkey assay. On the basis of its potency and duration of action, compound 1a (BMS-186716) was advanced into clinical development for the treatment of hypertension and congestive heart failure.

  DOI：

  10.1021/jm970041e
• 作为产物：
  描述：

  DL-高半胱氨酸硫内酯盐酸盐 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以35%的产率得到N-Benzyloxycarbonyl-D,L-homocystein-thiolacton
  参考文献：
  名称：

  Syntheses of Sequence-Controlled Polymers via Consecutive Multicomponent Reactions

  摘要：

  Multicomponent reactions have recently attracted a great deal of attention as they are considered as a powerful tool for constructing sequence-controlled polymers. Although new examples are constantly flourishing in the literature, the process that allows two or more consecutive multicomponent-reactions to react in a single operation for the syntheses of sequence-controlled polymers has not been developed until now. Here, we propose a new strategy combining multicomponent reaction of amine, thiol, and alkene conjugating and multicomponent polymerization of diyne, azide, and diamine coupling in one-pot for the synthesis of sequence-controlled polymer.

  DOI：

  10.1021/acs.macromol.5b00463

文献信息

• Synthesis and in vitro enzyme activity of aza, oxa and thia derivatives of bacterial cell wall biosynthesis intermediates†
  作者：Russell J. Cox、Paul S. H. Wang

  DOI：10.1039/b105117m

  日期：——

  Mechanism based inhibitors of diaminopimelate aminotransferase (DAP-AT) were designed using knowledge of its substrate specificity and mechanism. Synthesis of thiolester and amide substrate analogues was achieved prior to in vitro inhibition studies, but ester analogues proved too unstable to isolate. Thia substrate analogues showed no inhibitory properties, but the aza substrate analogue 12a showed reversible inhibition vs. DAP-AT and time dependent inhibition in the absence of the natural substrate 4. Substrate analogue 12a is the first example of an amide inhibitor of PLP dependent enzymes. Antibiotic properties of 12a were also briefly assessed.

  基于对二氨基庚二酸转氨酶（DAP-AT）的底物特异性及作用机制的了解，设计了机制型抑制剂。在体外抑制实验之前，成功合成了硫酯及酰胺类底物类似物，但酯类类似物过于不稳定，无法分离。硫类底物类似物未表现出抑制作用，但氮类底物类似物12a对DAP-AT显示出可逆抑制性，并且在缺乏天然底物4的情况下显示出时间依赖性抑制作用。底物类似物12a是首个PLP依赖性酶的酰胺类抑制剂示例。同时，也对12a的抗菌特性进行了简要评估。
• Schroeder,E. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 646, p. 101 - 118
  作者：Schroeder,E. et al.

  DOI：——

  日期：——
• Knobler,Y. et al., Israel Journal of Chemistry, 1970, vol. 8, p. 639 - 645
  作者：Knobler,Y. et al.

  DOI：——

  日期：——
• Drugs of the Future 1999, 24, 269-277
  作者：

  DOI：——

  日期：——
• J. Med. Chem. 1997, 40, 1570-1577
  作者：

  DOI：——

  日期：——