N-(2-Aminoethyl)glycinamide | 84354-31-4

• 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: N-(2-Aminoethyl)glycinamide
• 英文别名: N-glycylethylenediamine；N-Glycyl-ethylendiamin；2-Amino-N-(2-aminoethyl)acetamide
• CAS: 84354-31-4
• 化学式: C₄H₁₁N₃O
• 分子量: 117.151
• InChiKey: NFSGQYGMPDCEFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  81.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-Aminoethyl)glycinamide 生成 desferrioxamine P₁
  参考文献：
  名称：

  Solution thermodynamics of the ferric complexes of new desferrioxamine siderophores obtained by directed fermentation

  摘要：

  Thirteen new desferrioxamine-type siderophores, designated X1-X6, Et1-Et3, Te1-Te3, and P1, were obtained from cultures of Streptomyces olivaceus Tu 2718 by supplementing the production medium with ornithine or 1,4-diaminobutane, 1,6-diaminohexane, bis(2-aminoethyl) ether, S-(2-aminoethyl)cysteine, and N-glycylethylenediamine. The stability constants of the ferric complexes of the trihydroxamate ligands, X1-X4, Et1-Et3, and Te1-Te3, were determined by EDTA competition reactions and are in the range log beta-110 = 29.7-31.8 (beta-110 = [FeL]/([Fe3+] [L3-], 25-degrees-C, 0.1 M KNO3). The stability of the complexes decreases monotonically as the structure of the ligand differs from that of desferrioxamine E (beta-110 = 32.21, 25-degrees-C, 0.1 M KNO3), the main siderophore of S. olivaceus Tu 2718 under natural growth conditions. The dihydroxamic acid desferrioxamine X5 forms two types of ferric complexes, depending on pH. The predominant species above pH 6.4 is a dimer of formulation Fe2L3, Which dissociates into a monomeric cation, FeL+, at lower pH. The stability constants of these two species determined by spectrophotometric titration are log beta-230 = 55.35 and log beta-110 = 19.18 (25-degrees-C, 0.1 M KNO3). The relative effectiveness of the new ferrioxamines as mediators of iron uptake via the hydroxamate ferric ion transport system of Staphylococcus aureus DSM 799 differs widely, however, without correlating with the complex stability.

  DOI：

  10.1021/ja00032a043
• 作为产物：
  描述：

  benzyl N-[2-oxo-2-[2-(phenylmethoxycarbonylamino)ethylamino]ethyl]carbamate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 N-(2-Aminoethyl)glycinamide
  参考文献：
  名称：

  Potential antitumor agents. 44. Synthesis and antitumor activity of new classes of diacridines: importance of linker chain rigidity for DNA binding kinetics and biological activity

  摘要：

  Four classes of diacridines, joined at the 9-position by linker chains of varying length, rigidity, and polarity, were evaluated for DNA-binding properties and antitumor activity. Diacridines linked by flexible chains of varying polarity show relatively fast chromophore exchange kinetics among DNA binding sites but slower dissociation rates, suggesting the potential for considerable "creeping" of the drug along the helix, and are inactive in vivo. The exchange kinetics can be slowed dramatically by inclusion of positive charges in the side chain, but the resulting polycationic drugs are inactive in vivo, possibly due to poor distribution. Diacridines linked by a rigid, polar but neutral dicarbamoylpyrazole chain retain slow exchange kinetics, have a greatly reduced potential "creep rate", and possess good in vitro potency and significant in vivo antileukemic activity.

  DOI：

  10.1021/jm00149a005

文献信息

• Noguchi,J. et al., Israel Journal of Chemistry, 1974, vol. 12, p. 87 - 101
  作者：Noguchi,J. et al.

  DOI：——

  日期：——
• Synthesis and Evaluation of Novel Macrocyclic and Acyclic Ligands as Contrast Enhancement Agents for Magnetic Resonance Imaging
  作者：Hyun-Soon Chong、Kayhan Garmestani、L. Henry Bryant,、Diane E. Milenic、Terrish Overstreet、Noah Birch、Thien Le、Erik D. Brady、Martin W. Brechbiel

  DOI：10.1021/jm051009k

  日期：2006.3.1

  Novel chelates PIP-DTPA, AZEP-DTPA, NETA, NPTA, and PIP-DOTA were synthesized and evaluated as potential magnetic resonance imaging (MRI) contrast enhancement agents. The T-1 and T-2 relaxivities of their corresponding Gd(III) complexes are reported. At clinically relevant field strengths, the relaxivities of the complexes are comparable to that of the clinically used contrast agents Gd(DTPA) and Gd(DOTA). The serum stability of the Gd-153-labeled complexes, Gd(PIP-DTPA), Gd(AZEP-DTPA), Gd(PIP-DOTA), Gd(NETA), and Gd(NPTA), was assessed by measuring the release of Gd-153 from the complexes. Gd-153(NETA), Gd-153(PIP-DTPA), and Gd-153(PIP-DOTA) were found to be stable in human serum for up to 14 days without any measurable loss of radioactivity. Significant release of Gd-153 was observed with the Gd-153(III) radiolabled NPTA. In vivo biodistribution of the Gd-153-labeled complexes was performed to evaluate their in vivo stability. While Gd(AZEP-DTPA) and Gd(NPTA) were found to be unstable in vivo, Gd(NETA), Gd(PIP-DTPA), and Gd(PIP-DOTA) were excreted without dissociation. These results suggest that the Gd(III) complexes of the novel chelates NETA, PIP-DTPA, and PIP-DOTA possess potential as MRI contrast enhancement agents. In particular, the piperidine backboned chelates Gd(PIP-DTPA) and Gd(PIP-DOTA) displayed reduced kidney retention as compared to the nonspecific MRI contrast agent Gd(DOTA) at all time points, although the observed effects were relatively small at 0.5 h postinjection. Incorporation of the lipophilic piperidine ring appears to confer a moderate effect on the liver uptake of these two chelates.
• FIEDLER, H. -P.;MEIWES, J.;WERNER, I.;KONETSCHNY-RAPP, S.;JUNG, G., J. CHROMATOGR., 513,(1990) C. 255-262
  作者：FIEDLER, H. -P.、MEIWES, J.、WERNER, I.、KONETSCHNY-RAPP, S.、JUNG, G.

  DOI：——

  日期：——
• DENNY, W. A.;ATWELL, G. J.;BAGULEY, B. C.;WAKALIN, L. P. G., J. MED. CHEM., 1985, 28, N 11, 1568-1574
  作者：DENNY, W. A.、ATWELL, G. J.、BAGULEY, B. C.、WAKALIN, L. P. G.

  DOI：——

  日期：——
• Design of ligands containing the o-hydroxybenzyl group. Metal-complexing properties of N,N″-bis(2-hydroxybenzyl)diethylenetriamine-N,N′,N″-triacetic acid
  作者：Robert D. Hancock、Ignacy Cukrowski、Ewa Cukrowska、Gladys D. Hosken、Vimal Iccharam、Martin W. Brechbiel、Otto A. Gansow

  DOI：10.1039/dt9940002679

  日期：——

  The ligand N,N''-bis(2-hydroxybenzyl)diethylenetriamine-N,N',N''-triacetic acid (H(5)L) has been synthesised and the protonation constants for L determined by potentiometric methods in 0.5 mol dm(-3) NaNO3, and spectrophotometric methods in 0.5 and 0.1 mol dm(-3) NaCl, all at 25 degrees C. The sites of protonation have been inferred from H-1 NMR studies in D2O. The complex formation constants of Ca-II, Zn-II Cd-II, Cu-II, Pb-II and Bi-III have been determined at 25 degrees C by potentiometric methods in 0.5 mol dm(-3) NaNO3, and spectrophotometric methods in 0.5 mol dm(-3) NaCl. The results show that at biological pH the hydroxybenzyl groups tend to remain protonated, and over most of the pH range protonated complexes dominate, with fully deprotonated complexes occurring only at pH values above 9 or 10. The ligand L is, compared to some of its analogues, effectively a weak complexing agent. This is rationalised in terms of the six-membered chelate rings formed in the complex, which include the hydroxybenzyl group. The six-membered chelate rings destabilize complexes of the larger metal ions with which the octadentate ligand should prefer to co-ordinate.