2-[5-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylmethoxyethyl]tetrazol-1-yl]ethyl acetate | 295338-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[5-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylmethoxyethyl]tetrazol-1-yl]ethyl acetate
• CAS: 295338-31-7
• 化学式: C₁₉H₂₇N₅O₅
• 分子量: 405.454
• InChiKey: DALPQMGAMFJAKU-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[5-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylmethoxyethyl]tetrazol-1-yl]ethyl acetate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 1-(β-hydroxyethyl)-5-(α-R-tert-butyloxycarbonylamino-β-benzyloxyethyl)tetrazole
  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：

  2-[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoyl]amino]ethyl acetate 在 叠氮基三甲基硅烷 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以85%的产率得到2-[5-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylmethoxyethyl]tetrazol-1-yl]ethyl acetate
  参考文献：
  名称：

  Discovery of a Tetrazole-Based Growth Hormone Secretagogue:  4-(Hydroxybutyl)carbamic Acid 2-{5-[1-(2-Amino-2-methylpropionylamino)-2- benzyloxyethyl]tetrazol-1-yl}ethyl Ester (BMS-317180)

  摘要：

  A tetrazole-based peptidomimetic 2 (BMS-317180) was discovered as a human growth hormone secretagogue (GHS). Compound 2 is a potent, novel, orally effective GHS that shows an excellent safety profile in preclinical studies. The compound was advanced into clinical development.

  DOI：

  10.1021/jm7010595

文献信息

• Tetrazole based amides as growth hormone secretagogues
  作者：James J. Li、Haixia Wang、Jun Li、Fucheng Qu、Stephen G. Swartz、Andrés S. Hernández、Scott A. Biller、Jeffrey A. Robl、Joseph A. Tino、Dorothy Slusarchyk、Ramakrishna Seethala、Paul Sleph、Mujing Yan、Gary Grover、Neil Flynn、Brian J. Murphy、David Gordon

  DOI：10.1016/j.bmcl.2008.03.059

  日期：2008.4

  A novel series of N1 substituted tetrazole amides were prepared and showed to be potent growth hormone (GH) secretagogues. Among them, hydroxyl containing analog 31 displayed excellent in vivo activity by increasing plasma GH 10-fold in an anesthetized IV rat model. (c) 2008 Elsevier Ltd. All rights reserved.