2‑(1,3‑dioxoisoindolin‑2‑yl)acetyl methyl leucinate | 27462-45-9

• 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: 2‑(1,3‑dioxoisoindolin‑2‑yl)acetyl methyl leucinate
• 英文别名: N-(N,N-phthaloyl-glycyl)-L-leucine-methyl ester；N-(N,N-Phthaloyl-glycyl)-L-leucin-methylester；methyl (2S)-2-[[2-(1,3-dioxoisoindol-2-yl)acetyl]amino]-4-methylpentanoate
• CAS: 27462-45-9
• 化学式: C₁₇H₂₀N₂O₅
• mdl: MFCD03270212
• 分子量: 332.356
• InChiKey: SZIPLDVGDUNKQW-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2‑(1,3‑dioxoisoindolin‑2‑yl)acetyl methyl leucinate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 methyl glycyl-L-leucinate hydrochloride
  参考文献：
  名称：

  Novel thiazolidinedione-5-acetic-acid-peptide hybrid derivatives as potent antidiabetic and cardioprotective agents

  摘要：

  Thiazolidinediones (TZDs) are one of the important clinically established antidiabetic agents. Aminoacid and peptides have an advantage of better target selectivity and specificity. As hybrids, they also improved absorption and showed better bioavailability, which in turn makes them safer. Hence, here an effort has been made to synthesize hybrids of thiazolidinedione with amino-acids and peptides and evaluate their antidiabetic and cardioprotective effect in streptozotocin-nicotinamide (STZ-NA) induced Type 2 diabetes mellitus (T2DM) rat models.A series of 14 thiazolidinedione-5-acetic acid hybrids with of different amino-acids and peptide combinations were synthesized, characterized and further screened for antidiabetic and cardioprotective activity.Among all, six compounds T1 (SSDMA1), T4 (SSDMA4), T5 (SSDMA5), T7 (SDMA13), T9 (SSDMA15) and T13 (SSDMA49) showed better antioxidant activity and comparable % glucose uptake by yeast cells.Hence, the in vivo antidiabetic screening was done for these six compounds. Among all six T1, T7, T13 showed significant blood glucose level decrease compared to standard pioglitazone HCl. Also T1, T7 and T13 showed better antioxidant activity with lower IC50 value than standard ascorbic acid, and hence in vivo cardioprotective studies were done for these. The ECG studies showed that T1 (SSDMA1) and T7 (SSDMA13) were better effective than SDMA49 (T13) in restoring the normal functioning of the heart, thus may help in preventing the development of diabetic cardiomyopathy (DCM) and controlling T2DM. (C) C 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biopha.2017.01.160
• 作为产物：
  描述：

  苯酐 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 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 48.5h， 生成 2‑(1,3‑dioxoisoindolin‑2‑yl)acetyl methyl leucinate
  参考文献：
  名称：

  新型 N-邻苯二甲酰甘氨酸衍生物的合成、分子对接和抗癫痫活性

  摘要：

  沙利度胺（α - N-邻苯二甲酰亚胺-戊二酰亚胺）是一种已被停用的镇静剂，最近重新成为抗癫痫的有效药物。在这项研究中，五升α-氨基酸的衍生物Ñ -phthaloylglycine合成和戊四唑（PTZ）诱发的癫痫发作的小鼠模型中测试。N-邻苯二甲酰甘氨酸通过邻苯二甲酸酐和甘氨酸在甲苯中三乙胺存在下回流反应制备。制备精氨酸、谷氨酰胺、亮氨酸、苯丙氨酸和色氨酸甲酯并与N使用偶联剂（EDC 和 HOBt）的邻苯二甲酰甘氨酸。最终化合物通过光谱方法（1H NMR、13 CNMR、IR 和 MS）进行表征。使用 AutoDock 4.2 进行了对接研究，以预测合成化合物对 GABA A受体的可能相互作用。所有化合物都进行了表征，停靠在 GABA A受体的结合口袋中，并在戊四唑诱导的小鼠癫痫发作中进行了测试。正如所料，计算机研究表明所有化合物都与 GABA A受体有效相互作用。所有合成的化合物都显示出令

  DOI：

  10.1007/s13738-021-02467-7

文献信息

• A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds
  作者：Yaxin Wang、Guo-Xing Li、Guohui Yang、Gang He、Gong Chen

  DOI：10.1039/c5sc04169d

  日期：——

  A highly tunable radical-mediated reaction system for the functionalization of tertiary aliphatic C–H bonds was developed. Reactions of various substrates with the Zhdankin azidoiodane reagent 1, Ru(bpy)3Cl2, and visible light irradiation at room temperature gave C–H azidated or halogenated products in an easily controllable fashion. These reactions are efficient, selective, and compatible with complex

  开发了一种高度可调的自由基介导的反应系统，用于脂肪族叔 C-H 键的功能化。各种底物与 Zhdankin 叠氮碘烷试剂1、Ru(bpy) 3 Cl 2的反应以及室温下可见光照射，以易于控制的方式产生 C-H 叠氮化或卤化产物。这些反应高效、有选择性且与复杂底物兼容。它们提供了一种潜在的有价值的工具，用于选择性地标记有机和生物分子的三级 C-H 键，并带有不同化学和生物物理特性的标签，以进行比较功能研究。
• Panneman et al., Recueil des Travaux Chimiques des Pays-Bas, 1959, vol. 78, p. 487,499
  作者：Panneman et al.

  DOI：——

  日期：——
• Novel thiazolidinedione-5-acetic-acid-peptide hybrid derivatives as potent antidiabetic and cardioprotective agents
  作者：D. Maji、S. Samanta

  DOI：10.1016/j.biopha.2017.01.160

  日期：2017.4

  Thiazolidinediones (TZDs) are one of the important clinically established antidiabetic agents. Aminoacid and peptides have an advantage of better target selectivity and specificity. As hybrids, they also improved absorption and showed better bioavailability, which in turn makes them safer. Hence, here an effort has been made to synthesize hybrids of thiazolidinedione with amino-acids and peptides and evaluate their antidiabetic and cardioprotective effect in streptozotocin-nicotinamide (STZ-NA) induced Type 2 diabetes mellitus (T2DM) rat models.A series of 14 thiazolidinedione-5-acetic acid hybrids with of different amino-acids and peptide combinations were synthesized, characterized and further screened for antidiabetic and cardioprotective activity.Among all, six compounds T1 (SSDMA1), T4 (SSDMA4), T5 (SSDMA5), T7 (SDMA13), T9 (SSDMA15) and T13 (SSDMA49) showed better antioxidant activity and comparable % glucose uptake by yeast cells.Hence, the in vivo antidiabetic screening was done for these six compounds. Among all six T1, T7, T13 showed significant blood glucose level decrease compared to standard pioglitazone HCl. Also T1, T7 and T13 showed better antioxidant activity with lower IC50 value than standard ascorbic acid, and hence in vivo cardioprotective studies were done for these. The ECG studies showed that T1 (SSDMA1) and T7 (SSDMA13) were better effective than SDMA49 (T13) in restoring the normal functioning of the heart, thus may help in preventing the development of diabetic cardiomyopathy (DCM) and controlling T2DM. (C) C 2017 Elsevier Masson SAS. All rights reserved.
• Synthesis, molecular docking, and antiepileptic activity of new N-phthaloylglycine derivatives
  作者：Mona khademi、Fatemeh Moradkhani、Faezeh Sadat Hosseini、Mehdi Asadi、Arash Amanlou、Reza Khorasani、Ahmadreza Barazesh Morgani、Massoud Amanlou

  DOI：10.1007/s13738-021-02467-7

  日期：2022.6

  phenylalanine methyl ester derivative of N-phthaloylglycine (6d) had antiepileptic effects even more potent than thalidomide. Increasing lipophilicity and facilitating compounds delivery through l-amino acid carriers to the brain appear to be responsible for the remarkable activity of these compounds. Both in silico and in vivo results suggest that the l-amino acid derivatives of N-phthaloylglycine act

  沙利度胺（α - N-邻苯二甲酰亚胺-戊二酰亚胺）是一种已被停用的镇静剂，最近重新成为抗癫痫的有效药物。在这项研究中，五升α-氨基酸的衍生物Ñ -phthaloylglycine合成和戊四唑（PTZ）诱发的癫痫发作的小鼠模型中测试。N-邻苯二甲酰甘氨酸通过邻苯二甲酸酐和甘氨酸在甲苯中三乙胺存在下回流反应制备。制备精氨酸、谷氨酰胺、亮氨酸、苯丙氨酸和色氨酸甲酯并与N使用偶联剂（EDC 和 HOBt）的邻苯二甲酰甘氨酸。最终化合物通过光谱方法（1H NMR、13 CNMR、IR 和 MS）进行表征。使用 AutoDock 4.2 进行了对接研究，以预测合成化合物对 GABA A受体的可能相互作用。所有化合物都进行了表征，停靠在 GABA A受体的结合口袋中，并在戊四唑诱导的小鼠癫痫发作中进行了测试。正如所料，计算机研究表明所有化合物都与 GABA A受体有效相互作用。所有合成的化合物都显示出令