1-[4-azidobutyl]cyclopentanecarboxylic acid | 220878-37-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-[4-azidobutyl]cyclopentanecarboxylic acid
• 英文别名: 1-(4-Azidobutyl)cyclopentanecarboxylic acid；1-(4-azidobutyl)cyclopentane-1-carboxylic acid
• CAS: 220878-37-5
• 化学式: C₁₀H₁₇N₃O₂
• 分子量: 211.264
• InChiKey: LHSKXJBTISJUNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[4-azidobutyl]cyclopentanecarboxylic acid 在 sodium hydroxide 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (S)-2-{[1-(4-Azido-butyl)-cyclopentanecarbonyl]-amino}-3-[4-(2,6-dichloro-benzoylamino)-phenyl]-propionic acid
  参考文献：
  名称：

  N-Cycloalkanoyl-l-Phenylalanine Derivatives as VCAM/VLA-4 Antagonists

  摘要：

  A systematic structure-activity relationship investigation of the lead compound I resulted the identification of several N-[(substituted alkyl)cycloalkanoyl]-4-[((2,6-dichlorophenyl)carbonyl)amino]-L-phenylalanine derivatives as potent VCAM/VLA-4 antagonists. The data are consistent with a model of these compounds in which these alkanoylphenylalanines reside in a compact gauche (-) bioactive conformation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00386-4
• 作为产物：
  描述：

  环戊烷甲酸甲酯 在 sodium hydroxide 、 sodium azide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 1-[4-azidobutyl]cyclopentanecarboxylic acid
  参考文献：
  名称：

  N-Cycloalkanoyl-l-Phenylalanine Derivatives as VCAM/VLA-4 Antagonists

  摘要：

  A systematic structure-activity relationship investigation of the lead compound I resulted the identification of several N-[(substituted alkyl)cycloalkanoyl]-4-[((2,6-dichlorophenyl)carbonyl)amino]-L-phenylalanine derivatives as potent VCAM/VLA-4 antagonists. The data are consistent with a model of these compounds in which these alkanoylphenylalanines reside in a compact gauche (-) bioactive conformation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00386-4

文献信息

• [EN] INTEGRIN ANTAGONIST CONJUGATES FOR TARGETED DELIVERY TO CELLS EXPRESSING VLA-4<br/>[FR] CONJUGUÉS D'ANTAGONISTES D'INTÉGRINE POUR CIBLER DES CELLULES EXPRIMANT LE VLA-4
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013110680A1

  公开（公告）日：2013-08-01

  The invention relates to compounds of formula I: wherein R1, R2, and n are defined in the detailed description and claims. In particular, the present invention relates to the compounds of formula I for use in the manufacture and delivery of conjugated moieties such as small molecules, peptides, nucleic acids, fluorescent moieties, and polymers which are linked to VLA-4 integrin antagonists to target cells expressing VLA-4.

  该发明涉及以下式I的化合物：其中R1、R2和n在详细说明和权利要求中有定义。具体而言，本发明涉及式I的化合物，用于制造和传递共轭基团，如小分子、肽、核酸、荧光基团和聚合物，这些基团与VLA-4整合素拮抗剂连接，以靶向表达VLA-4的细胞。
• N-alkanoylphenylalanine derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US06455550B1

  公开（公告）日：2002-09-24

  Compounds of the formula: are disclosed which have activity as inhibitors of binding between VCAM-1 and cells expressing VLA-4. Such compounds are useful for treating diseases whose symptoms and/or damage are related to the binding of VCAM-1 to cells expressing VLA-4.

  揭示了具有以下化学式的化合物，这些化合物具有作为VCAM-1和表达VLA-4的细胞之间结合抑制剂的活性。这些化合物对于治疗那些症状和/或损害与VCAM-1与表达VLA-4的细胞结合有关的疾病是有用的。
• N-alkanoylphenylalamine derivatives
  申请人：——

  公开号：US20030109459A1

  公开（公告）日：2003-06-12

  Compounds of the formula: 1 are disclosed which have activity as inhibitors of binding between VCAM-1 and cells expressing VLA-4. Such compounds are useful for treating diseases whose symptoms and/or damage are related to the binding of VCAM-1 to cells expressing VLA-4.

  本文披露了一种化合物，其化学式为1，具有抑制VCAM-1与表达VLA-4的细胞结合的活性。这些化合物可用于治疗症状和/或损伤与VCAM-1与表达VLA-4的细胞结合有关的疾病。
• INTEGRIN ANTAGONIST CONJUGATES FOR TARGETED DELIVERY TO CELLS EXPRESSING VLA-4
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150031715A1

  公开（公告）日：2015-01-29

  The invention relates to compounds of formula I: wherein R1, R2, and n are defined in the detailed description and claims. In particular, the present invention relates to the compounds of formula I for use in the manufacture and delivery of conjugated moieties such as small molecules, peptides, nucleic acids, fluorescent moieties, and polymers which are linked to VLA-4 integrin antagonists to target cells expressing VLA-4.

  本发明涉及I式化合物：其中R1，R2和n在详细说明和权利要求中定义。特别地，本发明涉及I式化合物的制造和传递，用于制造和传递与VLA-4整合素拮抗剂连接的共轭基团，例如小分子、肽、核酸、荧光基团和聚合物，以靶向表达VLA-4的细胞。
• Integrin antagonist conjugates for targeted delivery to cells expressing VLA-4
  申请人：Hoffmann-La Roche Inc.

  公开号：US09447035B2

  公开（公告）日：2016-09-20

  The invention relates to compounds of formula I: wherein R1, R2, and n are defined in the detailed description and claims. In particular, the present invention relates to the compounds of formula I for use in the manufacture and delivery of conjugated moieties such as small molecules, peptides, nucleic acids, fluorescent moieties, and polymers which are linked to VLA-4 integrin antagonists to target cells expressing VLA-4.

  本发明涉及公式I的化合物：其中R1、R2和n在详细说明和权利要求中定义。特别地，本发明涉及公式I的化合物，用于制造和传递共轭基团，如小分子、肽、核酸、荧光基团和聚合物，这些基团与VLA-4整合素拮抗剂连接以靶向表达VLA-4的细胞。