(2R)-3-[(2-chlorophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid | 616881-96-0

• 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: (2R)-3-[(2-chlorophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 616881-96-0
• 化学式: C₁₅H₂₀ClNO₅
• 分子量: 329.781
• InChiKey: TYXDWRUJFNBFSY-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-3-[(2-chlorophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid 、 C.I.酸性橙108 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 生成
  参考文献：
  名称：

  Design and synthesis of tetrazole-based growth hormone secretagogue: The SAR studies of the O-benzyl serine side chain

  摘要：

  The structure-activity relationship of the O-benzyl serine side chain was investigated based on the tetrazole-based growth hormone secretagogue BMS-317180 (2). The ortho position of the benzyl moiety was found to be favorable for introduction of substituents. A series of ortho-substituted compounds were synthesized with improved in-vitro and in-vivo activity. Among them, the biphenyl compound 2p shows twofold improvement in potency compared to its parent compound BMS- 317180 (2). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.021
• 作为产物：
  描述：

  BOC-D-丝氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 生成 (2R)-3-[(2-chlorophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
  参考文献：
  名称：

  Design and synthesis of tetrazole-based growth hormone secretagogue: The SAR studies of the O-benzyl serine side chain

  摘要：

  The structure-activity relationship of the O-benzyl serine side chain was investigated based on the tetrazole-based growth hormone secretagogue BMS-317180 (2). The ortho position of the benzyl moiety was found to be favorable for introduction of substituents. A series of ortho-substituted compounds were synthesized with improved in-vitro and in-vivo activity. Among them, the biphenyl compound 2p shows twofold improvement in potency compared to its parent compound BMS- 317180 (2). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.021

文献信息

• Growth hormone secretagogues
  申请人：Evers Britta

  公开号：US20050240001A1

  公开（公告）日：2005-10-27

  This invention relates to novel compounds which are useful in the modulation of endogenous growth hormone levels in a mammal. The invention further relates to novel intermediates for use in the synthesis of said compounds, as well as novel processes employed in these syntheses. Also included are methods of treating a mammal which include the administration of said compounds.

  本发明涉及一种新型化合物，该化合物在哺乳动物内调节内源性生长激素水平方面具有有用的作用。本发明还涉及用于合成所述化合物的新型中间体，以及用于这些合成的新型工艺。此外，还包括包括给予所述化合物的治疗哺乳动物的方法。
• GROWTH HORMONE SECRETAGOGUES
  申请人：ELI LILLY AND COMPANY

  公开号：EP1497316A2

  公开（公告）日：2005-01-19
• US7396846B2
  申请人：——

  公开号：US7396846B2

  公开（公告）日：2008-07-08
• [EN] GROWTH HORMONE SECRETAGOGUES<br/>[FR] SECRETAGOGUES D'HORMONES DE CROISSANCE
  申请人：LILLY CO ELI

  公开号：WO2003087070A2

  公开（公告）日：2003-10-23

  This invention relates to novel compounds of formula I wherein Q is SO2 or -CO- which are useful in the modulation of endogenous growth hormone levels in a mammal. The invention further relates to novel intermediates for use in the synthesis of said compounds, as well as novel processes employed in these syntheses. Also included are methods of treating a mammal which include the administration of said compounds.
• Design and synthesis of tetrazole-based growth hormone secretagogue: The SAR studies of the O-benzyl serine side chain
  作者：Jun Li、Stephanie Y. Chen、Shiwei Tao、Haixia Wang、James J. Li、Steve Swartz、Christa Musial、Andres A. Hernandez、Neil Flynn、Brian J. Murphy、Blake Beehler、Kenneth E. Dickinson、Leah Giupponi、Gary Grover、Ramakrishna Seethala、Paul Sleph、Dorothy Slusarchyk、Mujing Yan、William G. Humphreys、Hongjian Zhang、William R. Ewing、Jeffrey A. Robl、David Gordon、Joseph A. Tino

  DOI：10.1016/j.bmcl.2008.02.021

  日期：2008.3

  The structure-activity relationship of the O-benzyl serine side chain was investigated based on the tetrazole-based growth hormone secretagogue BMS-317180 (2). The ortho position of the benzyl moiety was found to be favorable for introduction of substituents. A series of ortho-substituted compounds were synthesized with improved in-vitro and in-vivo activity. Among them, the biphenyl compound 2p shows twofold improvement in potency compared to its parent compound BMS- 317180 (2). (C) 2008 Elsevier Ltd. All rights reserved.