N-叔丁氧羰基-N-甲基-O-叔丁基-L-酪氨酸 | 66638-37-7

• 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
• 中文名称: N-叔丁氧羰基-N-甲基-O-叔丁基-L-酪氨酸
• 英文名称: Boc-N-Me-L-Tyr(tBu)-OH
• 英文别名: N-(tert-butyloxycarbonyl)-O-(tert-butyl)-N-methyl-L-tyrosine；N-(t-butoxycarbonyl)-O-(t-butyl)-N-methyl-L-tyrosine；Boc-MeTyr(tBu)-OH；(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoic acid
• CAS: 66638-37-7
• 化学式: C₁₉H₂₉NO₅
• 分子量: 351.443
• InChiKey: KLLSBINBQFCWME-HNNXBMFYSA-N

物化性质

• 沸点：
  467.5±40.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-N-甲基-O-叔丁基-L-酪氨酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Unexpected stereochemical tolerance for the biological activity of tyroscherin

  摘要：

  Here we describe the concise syntheses of the 15 diastereomers and key analogs of the natural product tyroscherin. While systematic analysis of the analogs clearly demonstrated that the hydrocarbon tail is important for biological activity, structure-activity relationship studies of the complete tyroscherin diastereoarray revealed a surprisingly expansive stereochemical tolerance for the cytotoxic activity. Our results represent a departure from the tenet that biological activity is constrained to a narrow pharmacophore, and highlight the recently emerging appreciation for stereochemical flexibility in defining the essential structural elements of biologically active small molecules. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.027
• 作为产物：
  描述：

  Boc-O-叔丁基-L-酪氨酸 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-叔丁氧羰基-N-甲基-O-叔丁基-L-酪氨酸
  参考文献：
  名称：

  Unexpected stereochemical tolerance for the biological activity of tyroscherin

  摘要：

  Here we describe the concise syntheses of the 15 diastereomers and key analogs of the natural product tyroscherin. While systematic analysis of the analogs clearly demonstrated that the hydrocarbon tail is important for biological activity, structure-activity relationship studies of the complete tyroscherin diastereoarray revealed a surprisingly expansive stereochemical tolerance for the cytotoxic activity. Our results represent a departure from the tenet that biological activity is constrained to a narrow pharmacophore, and highlight the recently emerging appreciation for stereochemical flexibility in defining the essential structural elements of biologically active small molecules. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.027

文献信息

• Analgesic dipeptide amides and method of use and compositions thereof
  申请人：Sterling Drug Inc.

  公开号：US04454120A1

  公开（公告）日：1984-06-12

  A genus of dipeptide amides including as the preferred subgenus the dipeptide amides having the structural formula R.sub.1 TyrR.sub.2 D-Q-NR.sub.4 R.sub.5 wherein Q is Met, Met(O), Gln or Ser, R.sub.1 and R.sub.2 are each hydrogen or alkyl, R.sub.4 is phenylalkyl or substituted-phenylalkyl and R.sub.5 is hydrogen, alkyl, phenylalkyl, substituted-phenylalkyl or X-alkyl wherein X is an electronegative group are prepared by condensing the dipeptide with the amine or the amino acid with the amino acid amide and are useful as analgesics.

  一种二肽酰胺属，包括首选亚属为具有结构式R.sub.1 TyrR.sub.2 D-Q-NR.sub.4 R.sub.5的二肽酰胺，其中Q为Met、Met(O)、Gln或Ser，R.sub.1和R.sub.2分别为氢或烷基，R.sub.4为苯基烷基或取代苯基烷基，R.sub.5为氢、烷基、苯基烷基、取代苯基烷基或X-烷基，其中X为电负基团，通过将二肽与胺或氨基酸与氨基酸酰胺缩合制备，并可用作镇痛剂。
• US4454120A
  申请人：——

  公开号：US4454120A

  公开（公告）日：1984-06-12
• US4658013A
  申请人：——

  公开号：US4658013A

  公开（公告）日：1987-04-14