(S)-3-[3-Bromo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid | 1056968-51-4

• 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: (S)-3-[3-Bromo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
• 英文别名: (2S)-3-[3-bromo-5-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 1056968-51-4
• 化学式: C₂₆H₁₉BrF₃N₃O₄
• 分子量: 574.354
• InChiKey: DNYMWCUVFVGLGY-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-Bromo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-benzoic acid 、 (S)-3-[3-Bromo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 、 (S)-3-{3-Bromo-4-[(diethoxy-phosphoryl)-difluoro-methyl]-phenyl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 生成 {[2-Bromo-4-((S)-2-{(S)-2-[3-bromo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-benzoylamino]-3-[3-bromo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-propionylamino}-2-carbamoyl-ethyl)-phenyl]-difluoro-methyl}-phosphonic acid; compound with ammonia
  参考文献：
  名称：

  Synthesis of a novel peptidic photoaffinity probe for the PTP-1B enzyme

  摘要：

  The synthesis of a novel radioactive peptidic photoaffinity probe for the PTP-1B enzyme as well as some SAR leading to the choice of this compound as a photoaffinity probe are presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.101
• 作为产物：
  描述：

  (S)-3-[3-Bromo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-2-[(1S,2S,5S)-2-hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3Z)-ylideneamino]-propionic acid tert-butyl ester 在 水 、 碳酸氢钠 、 柠檬酸 作用下， 以 丙酮 为溶剂， 生成 (S)-3-[3-Bromo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
  参考文献：
  名称：

  Synthesis of a novel peptidic photoaffinity probe for the PTP-1B enzyme

  摘要：

  The synthesis of a novel radioactive peptidic photoaffinity probe for the PTP-1B enzyme as well as some SAR leading to the choice of this compound as a photoaffinity probe are presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.101

文献信息

• Ptb1b photoprobes
  申请人：Ramachandran Chidambaram

  公开号：US20070161542A1

  公开（公告）日：2007-07-12

  Photoaffinity probes (photoprobes) of the PTP1B enzyme contain the trifluoromethylphenyl diazirene photophore attached to compounds which bind to the PTP1B enzyme. The photoprobes bind irreversibly to the PTP1B enzyme upon irradiation, and can be used to study the binding of compounds to the PTP1B enzyme. Compounds that bind to the PTP1B enzyme may inhibit PTP1B and may be useful in the treatment of type 2 diabetes.

  PTP1B酶的光亲和探针（光探针）包含连接到与PTP1B酶结合的化合物的三氟甲基苯基重氮烷光团。在照射后，光探针不可逆地结合到PTP1B酶上，可用于研究化合物与PTP1B酶的结合。结合到PTP1B酶的化合物可能会抑制PTP1B，并可能在治疗2型糖尿病方面有用。
• [EN] PTP1B PHOTOPROBES<br/>[FR] PRHOTOSONDES PTP1B
  申请人：MERCK FROSST CANADA INC

  公开号：WO2005056582A1

  公开（公告）日：2005-06-23

  Photoaffinity probes (photoprobes) of the PTP1B enzyme contain the trifluoromethylphenyl diazirene photophore attached to compounds which bind to the PTP1B enzyme. The photoprobes bind irreversibly to the PTP1B enzyme upon irradiation, and can be used to study the binding of compounds to the PTP1B enzyme. Compounds that bind to the PTP1B enzyme may inhibit PTP1B and may be useful in the treatment of type 2 diabetes.
• Synthesis of a novel peptidic photoaffinity probe for the PTP-1B enzyme
  作者：Michel Thérien、Kathryn Skorey、Robert Zamboni、Chun Sing Li、Cheuk K Lau、Tammy LeRiche、Vouy Linh Truong、Deena Waddleton、Chidambaram Ramachandran

  DOI：10.1016/j.bmcl.2004.01.101

  日期：2004.5

  The synthesis of a novel radioactive peptidic photoaffinity probe for the PTP-1B enzyme as well as some SAR leading to the choice of this compound as a photoaffinity probe are presented. (C) 2004 Elsevier Ltd. All rights reserved.