methyl 2-(2-phthalimidoacetamido)acetate | 5033-17-0

• 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 2-(2-phthalimidoacetamido)acetate
• 英文别名: N-phthaloylglycylglycine methyl ester；Phth-Gly-Gly-OMe；N-(N,N-phthaloyl-glycyl)-glycine methyl ester；N-(N,N-Phthaloyl-glycyl)-glycin-methylester；Methyl {[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-YL)acetyl]amino}acetate；methyl 2-[[2-(1,3-dioxoisoindol-2-yl)acetyl]amino]acetate
• CAS: 5033-17-0
• 化学式: C₁₃H₁₂N₂O₅
• 分子量: 276.249
• InChiKey: FCYZYMYNUSFBRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-phthalimidoacetamido)acetate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 甘氨酰甘氨酸甲酯盐酸盐
  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：

  邻苯二甲酰甘氨酸 在 chromium(VI) oxide 、 硫酸 、 水 、 臭氧 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 反应 23.5h， 生成 methyl 2-(2-phthalimidoacetamido)acetate
  参考文献：
  名称：

  Kashima, Choji; Okada, Rieko; Arao, Hideki, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1241 - 1244

  摘要：

  DOI：

文献信息

• Amide hydrogen exchange rates of model peptides in dimethyl sulphoxide solutions
  作者：J. Chrisment、J.J. Delpuech、W. Rajerison、C. Selve

  DOI：10.1016/s0040-4020(01)82055-x

  日期：1986.1

  Proton Transfers from and to the nitrogen atom (s) α (or α and β) of a doubly protected dipeptide. Gly-Gly or PG2. (or tripeptide : Gly-Gly-Gly or PG3) in anhydrous DMSO was followed by DMNR under conditions of both acid (sulphuric) and base (tetramethylguanidine) catalyzed exchange. Two kinetic processes are observed, one catalyzed by the hydrogen ion and the other by the conjugate base (P-) of the

  质子从被双重保护的二肽的氮原子α（或α和β）转移。Gly-Gly或PG 2。（或三肽：Gly-Gly-Gly或PG 3）在无水DMSO中，然后在酸（硫）和碱（四甲基胍）催化的交换条件下进行DMNR。观察到两个动力学过程，一个由氢离子催化，另一个由肽（P）的共轭碱（P-）催化。该方程式总结了在25°C下的结果。肽质子交换速率= k H [H + ] + k B [P] / [H + ]，其中k H = 6.3：17.1：8.85 M-ls -1和k B = 1.45; 5.62; 9.55×10 -13对于PG 2（α）和PG 3（α和β）分别为s -1。这使我们能够预测NH-NH（或NH-ND）交换的最大半反应时间。在DMSO中的pH为7至8时为10 4 mn。由log k H估算N-质子化的pK值（pK NH 2 +），并通过三种独立的方法测量N-去质子化的pK值（pK NH 2）。对于PG
• Bromination of N-phthaloylamino acid derivatives
  作者：Christopher J. Easton、Eng Wui Tan、Michael P. Hay

  DOI：10.1039/c39890000385

  日期：——

  Hydrogen transfer to the bromine atom from the α-position of N-phthaloylamino acid derivatives is disfavoured to such an extent that bromination of N-phthaloyl derivatives of valine and phenylalanine occurs regiospecifically at the β-position, while halogenation of N-phthaloyl derivatives of glycylglycine and glycylglycylvaline occurs selectively at the C-terminal and non-terminal glycine residues

  氢从N-邻苯二甲酰基氨基酸衍生物的α-位转移到溴原子的程度是不利的，使得缬氨酸和苯丙氨酸的N-邻苯二甲酰基的衍生物的溴化在β-位上发生区域特异性，而卤代N-邻苯二甲酰基的衍生物卤化。甘氨酰甘氨酸和甘氨酰甘氨酰缬氨酸分别选择性地出现在C末端和非末端甘氨酸残基上。
• <i>p</i>-Methoxybenzyl-Radical-Promoted Chemoselective Protection of <i>sec</i>-Alkylamides
  作者：JingWen Jia、Terumasa Kato、Keiji Maruoka

  DOI：10.1021/acs.joc.2c02582

  日期：2023.2.17

  The hitherto difficult site-selective p-methoxybenzylation of secondary amides using p-methoxybenzylated alkylsilyl peroxides as a novel p-methoxybenzylation agent under copper catalysis is reported. The reaction proceeds under mild reaction conditions in a highly chemoselective manner. This approach was successfully applied to the site-selective p-methoxybenzylation of peptides.

  据报道，在铜催化下，使用对甲氧基苄基化烷基过氧化物作为新型对甲氧基苄基化试剂，对仲酰胺进行迄今困难的位点选择性对甲氧基苄基化。该反应在温和的反应条件下以高度化学选择性的方式进行。该方法已成功应用于肽的位点选择性对甲氧基苄基化。
• Taschner et al., Roczniki Chemii, 1958, vol. 32, p. 1107,1110,1112
  作者：Taschner et al.

  DOI：——

  日期：——
• Wieland; Sehring, Justus Liebigs Annalen der Chemie, 1950, vol. 569, p. 122,128
  作者：Wieland、Sehring

  DOI：——

  日期：——