methyl <3'-(S)-<3'α,6'α(R*),7'aα>>-1-(tert-butoxycarbonyl)tetrahydro-5'-oxospirothiazolidine>-3'-carboxylate | 144085-26-7

• 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
• 英文名称: methyl <3'-(S)-<3'α,6'α(R*),7'aα>>-1-(tert-butoxycarbonyl)tetrahydro-5'-oxospirothiazolidine>-3'-carboxylate
• 英文别名: 1-O'-tert-butyl 3-O-methyl (3S,6R,7aR)-5-oxospiro[2,3,7,7a-tetrahydropyrrolo[2,1-b][1,3]thiazole-6,2'-pyrrolidine]-1',3-dicarboxylate
• CAS: 144085-26-7
• 化学式: C₁₆H₂₄N₂O₅S
• 分子量: 356.443
• InChiKey: OCOVBPVKPODIAH-GLKRBJQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl <3'-(S)-<3'α,6'α(R*),7'aα>>-1-(tert-butoxycarbonyl)tetrahydro-5'-oxospirothiazolidine>-3'-carboxylate 在 盐酸 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.5h， 生成
  参考文献：
  名称：

  Dopamine receptor modulation by a highly rigid spiro bicyclic peptidomimetic of Pro-Leu-Gly-NH2

  摘要：

  A peptidomimetic analogue of Pro-Leu-Gly-NH2 (PLG), compound 3, has been synthesized that contains a highly constrained spiro bicyclic type-II beta-turn mimic. Peptidomimetic 3 enhanced the binding of the dopamine receptor agonist ADTN to dopamine receptors by 40% at 10(-6) M. At this same concentration PLG enhanced the binding of ADTN by 26%. Like PLG, 3 exhibited a bell-shaped dose-response curve with the maximum effect occurring at a concentration of 10(-6) M. Because of the highly rigid nature of the spiro bicyclic type-II beta-turn constraint found in 3, these results lend strong support for the hypothesis that the biologically active conformation of PLG is a type-II beta-turn.

  DOI：

  10.1021/jm00074a032
• 作为产物：
  描述：

  (R)-2-烯丙基吡咯烷-2-羧酸 在 sodium hydroxide 、 sodium periodate 、 四氧化锇 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 101.0h， 生成 methyl <3'-(S)-<3'α,6'α(R*),7'aα>>-1-(tert-butoxycarbonyl)tetrahydro-5'-oxospirothiazolidine>-3'-carboxylate
  参考文献：
  名称：

  Genin, Michael J.; Johnson, Rodney L., Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8778 - 8783

  摘要：

  DOI：

文献信息

• Genin, Michael J.; Johnson, Rodney L., Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8778 - 8783
  作者：Genin, Michael J.、Johnson, Rodney L.

  DOI：——

  日期：——
• Dopamine receptor modulation by a highly rigid spiro bicyclic peptidomimetic of Pro-Leu-Gly-NH2
  作者：Michael J. Genin、Ram K. Mishra、Rodney L. Johnson

  DOI：10.1021/jm00074a032

  日期：1993.10

  A peptidomimetic analogue of Pro-Leu-Gly-NH2 (PLG), compound 3, has been synthesized that contains a highly constrained spiro bicyclic type-II beta-turn mimic. Peptidomimetic 3 enhanced the binding of the dopamine receptor agonist ADTN to dopamine receptors by 40% at 10(-6) M. At this same concentration PLG enhanced the binding of ADTN by 26%. Like PLG, 3 exhibited a bell-shaped dose-response curve with the maximum effect occurring at a concentration of 10(-6) M. Because of the highly rigid nature of the spiro bicyclic type-II beta-turn constraint found in 3, these results lend strong support for the hypothesis that the biologically active conformation of PLG is a type-II beta-turn.