(3S,6S,8aS)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid | 934660-55-6

• 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: (3S,6S,8aS)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid
• 英文别名: (3S,6S,8aS)-6-amino-5-oxo-2,3,6,7,8,8a-hexahydro-1H-indolizine-3-carboxylic acid
• CAS: 934660-55-6
• 化学式: C₉H₁₄N₂O₃
• 分子量: 198.222
• InChiKey: OIFVJUITQPXDAC-ACZMJKKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,6S,8aS)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N2-((3S,6S,8aS)-6-((S)-2-amino-4-(tert-butoxy)-4-oxobutanamido)-5-oxooctahydroindolizine-3-carbonyl)-Nw-((2,2,5,7,8-pentamethylchroman-6-yl)sulfonyl)-L-arginylglycine
  参考文献：
  名称：

  摘要：

  DOI：

  10.5555/ol007049u
• 作为产物：
  描述：

  Boc-L-焦谷氨酸甲酯 在 palladium on activated charcoal 三乙基硅烷 、 氢气 、 caesium carbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， -40.0 ℃ 、206.84 kPa 条件下， 反应 28.0h， 生成 (3S,6S,8aS)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid
  参考文献：
  名称：

  An Efficient Synthesis of the Constrained Peptidomimetic 2-Oxo-3-(N-9-fluorenyloxy-carbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic Acid from Pyroglutamic Acid

  摘要：

  Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo- [4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.

  DOI：

  10.1021/jo0515935

文献信息

• Inhibitors of signal transduction and activator of transcription 3
  申请人：McMurray S. John

  公开号：US20070010428A1

  公开（公告）日：2007-01-11

  Stat3 inhibitor compounds are disclosed, wherein the compounds are structural analogs of Ac-pTyr-Leu-Pro-Gln-Thr-NH 2 and bind to the SH2 domain of Stat3 under physiological conditions to inhibit a cellular signaling activity of Stat3.

  抑制剂化合物Stat3被披露，其中这些化合物是Ac-pTyr-Leu-Pro-Gln-Thr-NH2的结构类似物，并在生理条件下与Stat3的SH2结构域结合，从而抑制Stat3的细胞信号活性。
• NOVEL INHIBITORS OF HEPATITIS C VIRUS REPLICATION
  申请人：Buckman Brad

  公开号：US20110312996A1

  公开（公告）日：2011-12-22

  The embodiments provide compounds of the general Formulae VI, VII, VIII, IX, X, XI, XII, XIII, XIV, and XV as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

  本实施例提供了通式VI、VII、VIII、IX、X、XI、XII、XIII、XIV和XV的化合物，以及包括药物组合物在内的组合物。本实施例还提供了治疗方法，包括治疗丙型肝炎病毒感染和肝纤维化的方法，通常涉及向需要的个体施用所述化合物或组合物的有效量。
• Method of identifying inhibitors of CDC25
  申请人：——

  公开号：US20020183249A1

  公开（公告）日：2002-12-05

  The present invention relates to polypeptides which comprise the ligand binding domain of Cdc25, crystalline forms of these polypeptides and the use of these crystalline forms to determine the three dimensional structure of the catalytic domain of Cdc25. The invention also relates to the use of the three dimensional structure of the Cdc25 catalytic domain in methods of designing and/or identifying potential inhibitors of Cdc25 activity, for example, compounds which inhibit the binding of a native substrate to the Cdc25 catalytic domain.

  本发明涉及包含 Cdc25 配体结合结构域的多肽、这些多肽的结晶形式以及利用这些结晶形式确定 Cdc25 催化结构域的三维结构。本发明还涉及将 Cdc25 催化结构域的三维结构用于设计和/或鉴定 Cdc25 活性的潜在抑制剂的方法，例如，抑制原生底物与 Cdc25 催化结构域结合的化合物。
• [EN] NOVEL INHIBITORS OF HEPATITIS C VIRUS REPLICATION<br/>[FR] NOUVEAUX INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'HÉPATITE C
  申请人：INTERMUNE INC

  公开号：WO2011146401A1

  公开（公告）日：2011-11-24

  The embodiments provide compounds of the general Formulae (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), and (XV) as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.
• An Efficient Synthesis of the Constrained Peptidomimetic 2-Oxo-3-(<i>N</i>-9-fluorenyloxy-carbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic Acid from Pyroglutamic Acid
  作者：Pijus Kumar Mandal、Kumar K. Kaluarachchi、Douglas Ogrin、Simon G. Bott、John S. McMurray

  DOI：10.1021/jo0515935

  日期：2005.11.1

  Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo- [4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.