D-[(3S,5R)-3,5-bis(azidomethyl)]prolyl-L-valylglycine hydrochloride | 1480532-60-2

• 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: D-[(3S,5R)-3,5-bis(azidomethyl)]prolyl-L-valylglycine hydrochloride
• 英文别名: 2-[[(2S)-2-[[(2R,3S,5R)-3,5-bis(azidomethyl)pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]acetic acid;hydrochloride
• CAS: 1480532-60-2
• 化学式: C₁₄H₂₃N₉O₄*ClH
• 分子量: 417.855
• InChiKey: KAWXEDQAPPUEQT-LPUATBJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  D-[(3R,5S)-3,5-bis(azidomethyl)-1-(tert-butoxycarbonyl)]prolyl-L-valine 在 盐酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 44.5h， 生成 D-[(3S,5R)-3,5-bis(azidomethyl)]prolyl-L-valylglycine hydrochloride
  参考文献：
  名称：

  Synthesis and allosteric modulation of the dopamine receptor by peptide analogs of l-prolyl-l-leucyl-glycinamide (PLG) modified in the l-proline or l-proline and l-leucine scaffolds

  摘要：

  Novel analogs of L-prolyl-L-leucylglycinamide (PLC) were synthesized wherein the prolyl residue was replaced with other amino acids based on a 3,5-disubstituted proline scaffold. In some examples, the L-leucyl residue was also replaced by L-valine. These analogs were tested for their ability to enhance the binding of [H-3]-N-propylnorapomorphine to short isoform of human dopamine D-2 receptors.Compounds 18b and 19b, increased [H-3] NPA binding at concentrations between 10(-12) and 10(-9) M, which is similar to the effect of PLG in this assay and, provides evidences that these compounds are acting as allosteric modulators of dopamine D-2 receptors. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.001

文献信息

• Synthesis and allosteric modulation of the dopamine receptor by peptide analogs of l-prolyl-l-leucyl-glycinamide (PLG) modified in the l-proline or l-proline and l-leucine scaffolds
  作者：Joana Ferreira da Costa、Olga Caamaño、Franco Fernández、Xerardo García-Mera、Ivo E. Sampaio-Dias、José Manuel Brea、María Isabel Cadavid

  DOI：10.1016/j.ejmech.2013.08.001

  日期：2013.11

  Novel analogs of L-prolyl-L-leucylglycinamide (PLC) were synthesized wherein the prolyl residue was replaced with other amino acids based on a 3,5-disubstituted proline scaffold. In some examples, the L-leucyl residue was also replaced by L-valine. These analogs were tested for their ability to enhance the binding of [H-3]-N-propylnorapomorphine to short isoform of human dopamine D-2 receptors.Compounds 18b and 19b, increased [H-3] NPA binding at concentrations between 10(-12) and 10(-9) M, which is similar to the effect of PLG in this assay and, provides evidences that these compounds are acting as allosteric modulators of dopamine D-2 receptors. (C) 2013 Elsevier Masson SAS. All rights reserved.