[3'R-(3'β,6'α,8'aβ)]-1-[2(S)-pyrrolidinylcarbonyl]-5'-oxospiro[pyrrolidine-2,6'-thiazolidino[3,2-a]piperidine]-3'-carboxamide hydrochloride | 1140964-57-3

• 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: [3'R-(3'β,6'α,8'aβ)]-1-[2(S)-pyrrolidinylcarbonyl]-5'-oxospiro[pyrrolidine-2,6'-thiazolidino[3,2-a]piperidine]-3'-carboxamide hydrochloride
• CAS: 1140964-57-3
• 化学式: C₁₆H₂₄N₄O₃S*ClH
• 分子量: 388.918
• InChiKey: MWEBUIZFPAJLPK-NYHWTHLPSA-N

反应信息

• 作为产物：
  描述：

  [3'R-(3'β,6'α,8'aβ)]-1-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]carbonyl]-5'-oxospiro[pyrrolidine-2,6'-thiazolidino[3,2-a]piperidine]-3'-carboxamide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以20 mg的产率得到[3'R-(3'β,6'α,8'aβ)]-1-[2(S)-pyrrolidinylcarbonyl]-5'-oxospiro[pyrrolidine-2,6'-thiazolidino[3,2-a]piperidine]-3'-carboxamide hydrochloride
  参考文献：
  名称：

  Allosteric Modulation of the Dopamine D₂ Receptor by Pro-Leu-Gly-NH₂ Peptidomimetics Constrained in Either a Polyproline II Helix or a Type II β-Turn Conformation

  摘要：

  Type II beta-turn mimics and polyproline II helix mimics based upon diasterecisomeric 5.6.5 spiro bicyclic scaffolds have provided two pairs of Pro-Leu-Gly-NH2 (PLG) peptidomimetics with contrasting dopamine receptor modulating activities. Compounds 1a and 3a were found to be positive allosteric modulators of the dopamine receptor, while the corresponding diastereoisomeric compounds 1b and 3b provided the first PLG peptidomimetics with the ability to decrease the binding of agonists to the dopamine receptor. The positive allosteric modulating activity of 3a supported the hypothesis that a polyproline II helix conformation is the bioactive conformation for the PLG analogue Pro-Pro-Pro-NH2. The results also show that a change in the bridgehead chirality of the 5.6.5 scaffold brings about opposite effects in terms of the modulation of the dopamine receptor.

  DOI：

  10.1021/jm801575w