(S)-2-(butylaminocarbonyl)-5-oxopyrrolidine | 58620-89-6

• 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: (S)-2-(butylaminocarbonyl)-5-oxopyrrolidine
• 英文别名: (S)-N-butyl-5-oxopyrrolidine-2-carboxamide；5-oxo-L-proline-butylamide；5-Oxo-L-prolin-butylamid；L-pyroglutamic acid n-butyl amide；(2S)-N-butyl-5-oxopyrrolidine-2-carboxamide
• CAS: 58620-89-6
• 化学式: C₉H₁₆N₂O₂
• 分子量: 184.238
• InChiKey: UICDNADSGVMHKL-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(butylaminocarbonyl)-5-oxopyrrolidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以72%的产率得到(S)-2-(butylaminomethyl)pyrrolidine
  参考文献：
  名称：

  Preparation of Chiral Amine Carbonyl Chromium(0) Complexes with [(Norbornadiene)Cr(CO)4] as the Complexation Reagent

  摘要：

  A number of chiral amines were prepared and used as ligands in carbonylchromium(0) complexes. Included are monoamines, chelating diamines and methionine methyl ester, For their complexation (norbornadiene)tetracarbonylchromium(0) was found to allow complexation in high, sometimes quantitative yields in boiling THF (65 degrees C). The amine complexes prepared could be used as complexation reagents for arenes in up to 81% yield in the presence of boron trifluoride-diethyl ether adduct if THF was used as the solvent. Significant chirality transfer from the chiral complexation reagents to the chiral arene complexes was, however, not observed.

  DOI：

  10.1002/1099-0690(200006)2000:12<2273::aid-ejoc2273>3.0.co;2-m
• 作为产物：
  描述：

  正丁胺 、 L-焦谷氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以79%的产率得到(S)-2-(butylaminocarbonyl)-5-oxopyrrolidine
  参考文献：
  名称：

  天然产物铅合成l-焦谷氨酸类似物的合成和生物活性评估

  摘要：

  设计并合成了一系列来自天然产物铅的1-焦谷氨酸类似物，并描述了它们对疫霉菌的抗真菌活性，中枢神经活性，抗菌活性和消炎活性。生物测定和SAR研究表明，大多数1-焦谷氨酸酯类对P. infestans具有显着的抗真菌活性，尤其是2d和2j表现出最佳的活性，EC 50值为1.44和1.21μgmL -1，约为7倍于市售三氧化氮（7.85μgmL -1）。此外，化合物图2e，2g和4d显示了抗LPS诱导的BV-2小胶质细胞中NO产生的抗炎活性。NGF诱导的PC-12细胞中的神经生成活性是相同的。这项研究表明，化合物2d和2j是控制P. infestans的潜在药物。

  DOI：

  10.1016/j.bmc.2018.07.041

文献信息

• Pharmaceutical preparations having psychotropic activity and process for
  申请人：Hoechst Aktiengesellschaft

  公开号：US04053588A1

  公开（公告）日：1977-10-11

  Pharmaceutical preparations containing an L-pyroglutamic acid amide, processes for their preparation and methods of treating psychotic diseases with them.

  含有L-吡罗氨酸酰胺的制药制剂，其制备方法以及使用它们治疗精神病的方法。
• Notes - Some N-Substituted-5-oxo-2-pyrrolidinecarboxamides
  作者：R. B. Angier、V. K. Smith

  DOI：10.1021/jo01118a623

  日期：1956.12.1
• US4053588A
  申请人：——

  公开号：US4053588A

  公开（公告）日：1977-10-11
• Preparation of Chiral Amine Carbonyl Chromium(0) Complexes with [(Norbornadiene)Cr(CO)4] as the Complexation Reagent
  作者：Markus Strotmann、Holger Butenschön

  DOI：10.1002/1099-0690(200006)2000:12<2273::aid-ejoc2273>3.0.co;2-m

  日期：2000.6

  A number of chiral amines were prepared and used as ligands in carbonylchromium(0) complexes. Included are monoamines, chelating diamines and methionine methyl ester, For their complexation (norbornadiene)tetracarbonylchromium(0) was found to allow complexation in high, sometimes quantitative yields in boiling THF (65 degrees C). The amine complexes prepared could be used as complexation reagents for arenes in up to 81% yield in the presence of boron trifluoride-diethyl ether adduct if THF was used as the solvent. Significant chirality transfer from the chiral complexation reagents to the chiral arene complexes was, however, not observed.
• Synthesis and bioactivities evaluation of l-pyroglutamic acid analogues from natural product lead
  作者：Fang-li Gang、Feng Zhu、Xiao-ting Li、Jie-lu Wei、Wen-jun Wu、Ji-wen Zhang

  DOI：10.1016/j.bmc.2018.07.041

  日期：2018.9

  A series of l-pyroglutamic acid analogues from natural product lead were designed and synthesized, as well as their antifungal activities against Phytophthora infestans, neuritogenic activities, antibacterial activities and anti-inflammatory activities are described. The bioassays and SAR study showed that the majority of l-pyroglutamic acid esters have a significant antifungal activity against P.

  设计并合成了一系列来自天然产物铅的1-焦谷氨酸类似物，并描述了它们对疫霉菌的抗真菌活性，中枢神经活性，抗菌活性和消炎活性。生物测定和SAR研究表明，大多数1-焦谷氨酸酯类对P. infestans具有显着的抗真菌活性，尤其是2d和2j表现出最佳的活性，EC 50值为1.44和1.21μgmL -1，约为7倍于市售三氧化氮（7.85μgmL -1）。此外，化合物图2e，2g和4d显示了抗LPS诱导的BV-2小胶质细胞中NO产生的抗炎活性。NGF诱导的PC-12细胞中的神经生成活性是相同的。这项研究表明，化合物2d和2j是控制P. infestans的潜在药物。