N-<4-Methoxy-benzyliden>-phenylalanin | 192378-05-5

• 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-<4-Methoxy-benzyliden>-phenylalanin
• 英文别名: (2S)-2-[(4-methoxyphenyl)methylideneamino]-3-phenylpropanoic acid
• CAS: 192378-05-5
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: ISHPXGAPSXUXHW-INIZCTEOSA-N

物化性质

• 沸点：
  442.4±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<4-Methoxy-benzyliden>-phenylalanin 在 sodium tetrahydroborate 作用下， 反应 0.5h， 生成 N-(4-methoxybenzyl)-L-phenylalanine
  参考文献：
  名称：

  The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1

  摘要：

  The rationale for targeting the human di-/tripeptide transporter hPEPT1 for oral drug delivery has been well established by several drug and prodrug cases. The aim of this study was to synthesize novel ketomethylene modified tripeptidomimetics and to investigate their binding affinity for hPEPT1. Three related tripeptidomimetics of the structure H-Phe-psi[COCH2]-Ser(Bz)-X-aa-OH were synthesized applying the tandem chain extension aldol reaction, where amino acid derived beta-keto imides were stereoselectively converted to alpha-substituted gamma-keto imides. In addition, three corresponding tripeptides, composed of amide bonds, were synthesized for comparison of binding affinities. The six investigated compounds were all defined as high affinity ligands (K-i-values < 0.5 mM) for hPEPT1 by measuring the concentration dependent inhibition of apical [C-14]Gly-Sar uptake in Caco-2 cells. Consequently, the ketomethylene replacement for the natural amide bond and alpha-side chain modifications appears to offer a promising strategy to modify tripeptidic structures while maintaining a high affinity for hPEPT1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.108
• 作为产物：
  描述：

  L-苯丙氨酸 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以98%的产率得到N-<4-Methoxy-benzyliden>-phenylalanin
  参考文献：
  名称：

  金属β-内酰胺酶抑制剂的合成

  摘要：

  使用Ruppert试剂（TMS-CF 3）通过两条独立的途径合成了α-酰胺基三氟甲基醇和酮，它们是金属β-内酰胺酶的抑制剂。

  DOI：

  10.1016/s0040-4020(97)00404-3

文献信息

• Synthesis of metallo-β-lactamase inhibitors
  作者：Magnus W. Walter、Robert M. Adlington、Jack E. Baldwin、Christopher J. Schofield

  DOI：10.1016/s0040-4020(97)00404-3

  日期：1997.5

  α-Amido trifluoromethyl alcohols and ketones were synthesised via two independent routes using the Ruppert Reagent (TMS-CF3) and shown to be inhibitors of metallo-β-lactamases.

  使用Ruppert试剂（TMS-CF 3）通过两条独立的途径合成了α-酰胺基三氟甲基醇和酮，它们是金属β-内酰胺酶的抑制剂。
• Azomethine Chemistry. II. Formation of Peptides from Oxazolidine-5-ones
  作者：Richard G. Hiskey

  DOI：10.1021/ja00888a021

  日期：1963.3
• The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1
  作者：Karina Thorn、Carsten Uhd Nielsen、Palle Jakobsen、Bente Steffansen、Charles K. Zercher、Mikael Begtrup

  DOI：10.1016/j.bmcl.2011.05.108

  日期：2011.8

  The rationale for targeting the human di-/tripeptide transporter hPEPT1 for oral drug delivery has been well established by several drug and prodrug cases. The aim of this study was to synthesize novel ketomethylene modified tripeptidomimetics and to investigate their binding affinity for hPEPT1. Three related tripeptidomimetics of the structure H-Phe-psi[COCH2]-Ser(Bz)-X-aa-OH were synthesized applying the tandem chain extension aldol reaction, where amino acid derived beta-keto imides were stereoselectively converted to alpha-substituted gamma-keto imides. In addition, three corresponding tripeptides, composed of amide bonds, were synthesized for comparison of binding affinities. The six investigated compounds were all defined as high affinity ligands (K-i-values < 0.5 mM) for hPEPT1 by measuring the concentration dependent inhibition of apical [C-14]Gly-Sar uptake in Caco-2 cells. Consequently, the ketomethylene replacement for the natural amide bond and alpha-side chain modifications appears to offer a promising strategy to modify tripeptidic structures while maintaining a high affinity for hPEPT1. (C) 2011 Elsevier Ltd. All rights reserved.