1-allyloxycarbonyl-6-(S)-isobutyl-5-methylthio-3-oxo-3,6-dihydro-2H-pyrazine | 862835-57-2

• 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: 1-allyloxycarbonyl-6-(S)-isobutyl-5-methylthio-3-oxo-3,6-dihydro-2H-pyrazine
• 英文别名: (6S)-6-isobutyl-5-methylsulfanyl-3-oxo-3,6-dihydro-2H-pyrazine-1-carboxylic acid allyl ester；prop-2-enyl (2S)-2-(2-methylpropyl)-3-methylsulfanyl-5-oxo-2,6-dihydropyrazine-1-carboxylate
• CAS: 862835-57-2
• 化学式: C₁₃H₂₀N₂O₃S
• 分子量: 284.379
• InChiKey: MOGHWSUPWBTSFQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-allyloxycarbonyl-6-(S)-isobutyl-5-methylthio-3-oxo-3,6-dihydro-2H-pyrazine 、 L-缬氨酸叔丁酯盐酸盐 以 乙腈 为溶剂， 生成 (6S)-6-isobutyl-5-((1S)-1-t-butoxycarbonyl-2-methylpropylamino)-3-oxo-3,6-dihydro-2H-pyrazine-1-carboxylic acid allyl ester 、 (6R)-6-isobutyl-5-((1S)-1-t-butoxycarbonyl-2-methylpropylamino)-3-oxo-3,6-dihydro-2H-pyrazine-1-carboxylic acid allyl ester
  参考文献：
  名称：

  Peptide beta-strand mimics based on pyridinones, pyrazinones, pyridazinones, and triazinones

  摘要：

  肽类类似物中，通过将一个或多个氨基酸替换为二氮杂环己酮或三氮杂环己酮，或者通过将一个氮杂环己酮或二氮杂环己酮或三氮杂环己酮在α位用氨基酸的侧链取代，显示出改善的β链构象能力，并以一种亲和特异方式与肽相互作用形成类似β-折叠的结构。因此，本发明的肽类类似物作为β链模拟物具有优于天然肽和先前技术中的β链模拟物的优点。

  公开号：

  US20050187138A1
• 作为产物：
  描述：

  L-亮氨酰胺盐酸盐 在 劳森试剂 、 lithium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 42.1h， 生成 1-allyloxycarbonyl-6-(S)-isobutyl-5-methylthio-3-oxo-3,6-dihydro-2H-pyrazine
  参考文献：
  名称：

  Synthesis of Amino Acid-Derived Cyclic Acyl Amidines for Use in β-Strand Peptidomimetics

  摘要：

  The acyl amidine represented by the 4,5-dihydro-2(3H)-pyrazinone ring system 2 is isosteric to the vinylogous amide of the 1,2-dihydro-3(6H)-pyridinone 1, but its assembly from separate amine and amide components enables ready incorporation of an amino acid side chain with correct regio- and stereochemistry. beta-Strand peptidomimetics incorporating amino acid analogues based on 2 have recently been shown to be potent, protease-resistant ligands to a PDZ protein-interaction domain. Two routes to the protected dipeptide analogue 3 are described.

  DOI：

  10.1021/jo062664i

文献信息

• Peptide beta-strand mimics based on pyridinones, pyrazinones, pyridazinones, and triazinones
  申请人：Bartlett A. Paul

  公开号：US20050187138A1

  公开（公告）日：2005-08-25

  Peptide analogs in which one or more amino acids is replaced by a diaza- or triazacyclohexenone, or by an aza-, diaza-, or triazacyclohexenone that is substituted at the α-position with a side chain of an amino acid, display an improved ability to assume a β-strand conformation and to enter into β-sheet-like interactions with peptides in an affinity-specific manner. The peptide analogs of this invention therefore have utility as β-strand mimics offering advantages over both native peptides and β-strand mimics of the prior art.

  肽类类似物中，通过将一个或多个氨基酸替换为二氮杂环己酮或三氮杂环己酮，或者通过将一个氮杂环己酮或二氮杂环己酮或三氮杂环己酮在α位用氨基酸的侧链取代，显示出改善的β链构象能力，并以一种亲和特异方式与肽相互作用形成类似β-折叠的结构。因此，本发明的肽类类似物作为β链模拟物具有优于天然肽和先前技术中的β链模拟物的优点。
• Synthesis of Amino Acid-Derived Cyclic Acyl Amidines for Use in β-Strand Peptidomimetics
  作者：Ming C. Hammond、Paul A. Bartlett

  DOI：10.1021/jo062664i

  日期：2007.4.1

  The acyl amidine represented by the 4,5-dihydro-2(3H)-pyrazinone ring system 2 is isosteric to the vinylogous amide of the 1,2-dihydro-3(6H)-pyridinone 1, but its assembly from separate amine and amide components enables ready incorporation of an amino acid side chain with correct regio- and stereochemistry. beta-Strand peptidomimetics incorporating amino acid analogues based on 2 have recently been shown to be potent, protease-resistant ligands to a PDZ protein-interaction domain. Two routes to the protected dipeptide analogue 3 are described.