N'-(2-aminoethyl)-D-phenylalaninamide | 112670-61-8

• 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)-D-phenylalaninamide
• 英文别名: (2R)-2-amino-N-(2-aminoethyl)-3-phenylpropanamide
• CAS: 112670-61-8
• 化学式: C₁₁H₁₇N₃O
• 分子量: 207.275
• InChiKey: PTPSVHSULTZTGA-SNVBAGLBSA-N

物化性质

• 沸点：
  440.3±45.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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)-D-phenylalaninamide 在 盐酸 、 硼烷四氢呋喃络合物 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-4-benzyl-3,6,9-tris(carboxymethyl)-3,6,9-triazaundecanedioic acid
  参考文献：
  名称：

  各种苄基二亚乙基三胺五乙酸 (dtpa) 及其顺磁性配合物的合成和表征，磁共振成像的潜在造影剂

  摘要：

  Four derivatives of diethylenetriaminepentaacetic acid (= 3,6,9-tris(carboxymethyl)-3,6,9-triazaundecane-dioic acid (H(5)dtpa)), potential contrast agents for magnetic resonance imaging (MRI), carrying benzyl groups at various positions of the parent structure were synthesized and characterized by a thorough multinuclear NMR study, i.e., the (S)- and (R)-stereoisomers 1a and 1b of 4-benzyl-3,6,9-tris(carboxymethyl)-3,6,9-triazaundecanedioic acid (H-5[(S)-(4-Bz)dtpa] and H-5[(R)-(4-Bz)dtpa] the diamide derivative N,N'-bis{[benzylcarbamoyl)methyl}diethylenetriamine-N,N',N "-triacetic acid (= 3,9-bis[2-(benzylamino)-2-oxoethyl]-6-(carboxymethyl)-3,6,9-triazaundecanedioic acid: H-3[dtpa(BzA)(2)]: 2), and the diester derivative N,N "-bis([(benzyloxy)carbonyl]methyl]diethylenetriamine-N,N',N "-triacetic acid (= 3,9-bis[2-(benzyloxy)-2-oxoethyl]-6-(carboxymethyl)-3,6,9-triazaundecanedioic acid; H-3[dtpa(BzE)(2)]: 3). From the O-17-NMR chemical shift of H2O induced by their dysprosium complexes with ligands 1-3, it was concluded that only one H2O molecule is contained in the first coordination sphere of these lanthanide complexes. The rotational correlation times (tau(R)) of the complexes were estimated from the H-2-NMR longitudinal relaxation rate of the deuterated diamagnetic lanthanum complexes. The exchange lime of the coordinated H2O molecule (tau(M)) was studied through the temperature dependence of the O-17-NMR transverse relaxation rate. As compared to [Gd(dtpa)](2), the H2O-exchange rate is faster fur [Gd{(S)-(4-Bz)dtpa}](2) and [Gd{(R)-(4-Bz)dtpa}](2)-, slower for [Gd{dtpa(BzA)(2)}], and almost identical for [Gd{dtpa(BzE)(2)}]. The analysis of the H-1-relaxivity of the gadolinium complexes recorded from 0.02 to 300 MHz established that i) the relaxivity of [Gd{dtpa(BzE)(2)}] is similar to that of [Gd(dtpa)](2-), ii) the slightly slower molecular rotation of [Gd{dtpa(BzA)(2)}] induces a mild enhancement of its relaxivity, and iii) the marked increase of relaxivity of [Gd{(S)-(4-Bz)dtpa}](2) and [Gd{(R)-(4-Bz)dtpa}](2-) mainly results from an apparently shorter distance between the gadolinium ion and the H2O protons of the coordinated H2O molecule.

  DOI：

  10.1002/(sici)1522-2675(20000216)83:2<394::aid-hlca394>3.0.co;2-b
• 作为产物：
  描述：

  D-苯丙氨酸甲酯盐酸盐 、 乙二胺 在 三乙胺 作用下， 以89%的产率得到N'-(2-aminoethyl)-D-phenylalaninamide
  参考文献：
  名称：

  各种苄基二亚乙基三胺五乙酸 (dtpa) 及其顺磁性配合物的合成和表征，磁共振成像的潜在造影剂

  摘要：

  Four derivatives of diethylenetriaminepentaacetic acid (= 3,6,9-tris(carboxymethyl)-3,6,9-triazaundecane-dioic acid (H(5)dtpa)), potential contrast agents for magnetic resonance imaging (MRI), carrying benzyl groups at various positions of the parent structure were synthesized and characterized by a thorough multinuclear NMR study, i.e., the (S)- and (R)-stereoisomers 1a and 1b of 4-benzyl-3,6,9-tris(carboxymethyl)-3,6,9-triazaundecanedioic acid (H-5[(S)-(4-Bz)dtpa] and H-5[(R)-(4-Bz)dtpa] the diamide derivative N,N'-bis{[benzylcarbamoyl)methyl}diethylenetriamine-N,N',N "-triacetic acid (= 3,9-bis[2-(benzylamino)-2-oxoethyl]-6-(carboxymethyl)-3,6,9-triazaundecanedioic acid: H-3[dtpa(BzA)(2)]: 2), and the diester derivative N,N "-bis([(benzyloxy)carbonyl]methyl]diethylenetriamine-N,N',N "-triacetic acid (= 3,9-bis[2-(benzyloxy)-2-oxoethyl]-6-(carboxymethyl)-3,6,9-triazaundecanedioic acid; H-3[dtpa(BzE)(2)]: 3). From the O-17-NMR chemical shift of H2O induced by their dysprosium complexes with ligands 1-3, it was concluded that only one H2O molecule is contained in the first coordination sphere of these lanthanide complexes. The rotational correlation times (tau(R)) of the complexes were estimated from the H-2-NMR longitudinal relaxation rate of the deuterated diamagnetic lanthanum complexes. The exchange lime of the coordinated H2O molecule (tau(M)) was studied through the temperature dependence of the O-17-NMR transverse relaxation rate. As compared to [Gd(dtpa)](2), the H2O-exchange rate is faster fur [Gd{(S)-(4-Bz)dtpa}](2) and [Gd{(R)-(4-Bz)dtpa}](2)-, slower for [Gd{dtpa(BzA)(2)}], and almost identical for [Gd{dtpa(BzE)(2)}]. The analysis of the H-1-relaxivity of the gadolinium complexes recorded from 0.02 to 300 MHz established that i) the relaxivity of [Gd{dtpa(BzE)(2)}] is similar to that of [Gd(dtpa)](2-), ii) the slightly slower molecular rotation of [Gd{dtpa(BzA)(2)}] induces a mild enhancement of its relaxivity, and iii) the marked increase of relaxivity of [Gd{(S)-(4-Bz)dtpa}](2) and [Gd{(R)-(4-Bz)dtpa}](2-) mainly results from an apparently shorter distance between the gadolinium ion and the H2O protons of the coordinated H2O molecule.

  DOI：

  10.1002/(sici)1522-2675(20000216)83:2<394::aid-hlca394>3.0.co;2-b

文献信息

• Synthesis and Characterization of Various Benzyl Diethylenetriaminepentaacetic Acids (dtpa) and Their Paramagnetic Complexes, Potential Contrast Agents for Magnetic Resonance Imaging
  作者：Sophie Laurent、Luce Vander Elst、Sylvain Houzé、Nathalie Guérit、Robert N. Muller

  DOI：10.1002/(sici)1522-2675(20000216)83:2<394::aid-hlca394>3.0.co;2-b

  日期：2000.2.16

  Four derivatives of diethylenetriaminepentaacetic acid (= 3,6,9-tris(carboxymethyl)-3,6,9-triazaundecane-dioic acid (H(5)dtpa)), potential contrast agents for magnetic resonance imaging (MRI), carrying benzyl groups at various positions of the parent structure were synthesized and characterized by a thorough multinuclear NMR study, i.e., the (S)- and (R)-stereoisomers 1a and 1b of 4-benzyl-3,6,9-tris(carboxymethyl)-3,6,9-triazaundecanedioic acid (H-5[(S)-(4-Bz)dtpa] and H-5[(R)-(4-Bz)dtpa] the diamide derivative N,N'-bis[benzylcarbamoyl)methyl}diethylenetriamine-N,N',N "-triacetic acid (= 3,9-bis[2-(benzylamino)-2-oxoethyl]-6-(carboxymethyl)-3,6,9-triazaundecanedioic acid: H-3[dtpa(BzA)(2)]: 2), and the diester derivative N,N "-bis([(benzyloxy)carbonyl]methyl]diethylenetriamine-N,N',N "-triacetic acid (= 3,9-bis[2-(benzyloxy)-2-oxoethyl]-6-(carboxymethyl)-3,6,9-triazaundecanedioic acid; H-3[dtpa(BzE)(2)]: 3). From the O-17-NMR chemical shift of H2O induced by their dysprosium complexes with ligands 1-3, it was concluded that only one H2O molecule is contained in the first coordination sphere of these lanthanide complexes. The rotational correlation times (tau(R)) of the complexes were estimated from the H-2-NMR longitudinal relaxation rate of the deuterated diamagnetic lanthanum complexes. The exchange lime of the coordinated H2O molecule (tau(M)) was studied through the temperature dependence of the O-17-NMR transverse relaxation rate. As compared to [Gd(dtpa)](2), the H2O-exchange rate is faster fur [Gd(S)-(4-Bz)dtpa}](2) and [Gd(R)-(4-Bz)dtpa}](2)-, slower for [Gddtpa(BzA)(2)}], and almost identical for [Gddtpa(BzE)(2)}]. The analysis of the H-1-relaxivity of the gadolinium complexes recorded from 0.02 to 300 MHz established that i) the relaxivity of [Gddtpa(BzE)(2)}] is similar to that of [Gd(dtpa)](2-), ii) the slightly slower molecular rotation of [Gddtpa(BzA)(2)}] induces a mild enhancement of its relaxivity, and iii) the marked increase of relaxivity of [Gd(S)-(4-Bz)dtpa}](2) and [Gd(R)-(4-Bz)dtpa}](2-) mainly results from an apparently shorter distance between the gadolinium ion and the H2O protons of the coordinated H2O molecule.