1-Amino-3-diethoxyphosphorylpropan-2-one | 175027-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 1-Amino-3-diethoxyphosphorylpropan-2-one
• CAS: 175027-89-1
• 化学式: C₇H₁₆NO₄P
• 分子量: 209.182
• InChiKey: SZKNGHVVMWLHNB-UHFFFAOYSA-N

物化性质

• 沸点：
  302.8±27.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-L-苯丙氨酸苄酯 、 1-Amino-3-diethoxyphosphorylpropan-2-one 在 subtilisin BPN' 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Exploitation of Subtilisin BPN‘ as Catalyst for the Synthesis of Peptides Containing Noncoded Amino Acids, Peptide Mimetics and Peptide Conjugates

  摘要：

  The ability of the serine protease subtilisin BPN' to catalyze peptide bond formation between fragments containing noncoded amino acids, peptide mimetics, and peptide conjugates in a kinetic approach was explored. It was found that the enzyme accepts numerous of these types of compounds both as acyl donor and acyl acceptor. The results together with specificity studies reported by others provide an active site model as a guideline in the design of enzymatic synthesis of biologically important compounds.

  DOI：

  10.1021/ja964399w
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以95%的产率得到1-Amino-3-diethoxyphosphorylpropan-2-one
  参考文献：
  名称：

  Phosphonic acid and phosphinic acid tripeptides as inhibitors of glutathionylspermidine synthetase

  摘要：

  A series of phosphonic and phosphinic acid derivatives of glutathione were synthesized as potential inhibitors of glutathionylspermidine synthetase, an essential enzyme in the biosynthesis of trypanothione in trypanosomatids. The compounds showed moderate activity.

  DOI：

  10.1016/0960-894x(96)00001-7

文献信息

• Bioisosteres of 9-Carboxymethyl-4-oxo-imidazo[1,2- a ]indeno[1,2- e ]pyrazin-2-carboxylic acid derivatives. Progress towards selective, potent In Vivo AMPA antagonists with longer durations of action
  作者：Patrick Jimonet、Georg Andrees Bohme、Jean Bouquerel、Alain Boireau、Dominique Damour、Marc Williams Debono、Arielle Genevois-Borella、Jean-Claude Hardy、Philippe Hubert、Franco Manfré、Patrick Nemecek、Jeremy Pratt、John C.R. Randle、Yves Ribeill、Jean-Marie Stutzmann、Marc Vuilhorgne、Serge Mignani

  DOI：10.1016/s0960-894x(00)00592-8

  日期：2001.1

  A novel series of 2- and 9-disubstituted heterocyclic-fused 4-oxo-indeno[1,2-e]pyrazin derivatives was synthesized. One of them, the 9-(1 H-tetrazol-5-ylmethyl)-4-oxo-5,10-dihydroimidazo[1,2-a]indeno[1,2-e]pyrazin-2-yl phosphonic acid 4i exhibited a strong and a selective binding affinity for the AMPA receptor (IC50 = 13 nM) and demonstrated potent antagonist activity (IC50 = 6 nM) at the ionotropic AMPA receptor. This compound also displayed good anticonvulsant properties against electrically-induced convulsions after ip and iv administration with ED50 values between 0.8 and 1 mg/kg. Furthermore, a strong increase in potency was observed when given iv 3 h before test (ED50 = 3.5 instead of 25.6 mg/kg for the corresponding 9-carboxymethyl-2-carboxylic acid analogue). These data confirmed that there is an advantage in replacing the classical carboxy substituents by their bioisosteres such as tetrazole or phosphonic acid groups. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Phosphonic acid and phosphinic acid tripeptides as inhibitors of glutathionylspermidine synthetase
  作者：Christophe Verbruggen、Sofie De Craecker、Padinchare Rajan、Xian-Yun Jiao、Marianne Borloo、Keith Smith、Alan H. Fairlamb、Achiel Haemers

  DOI：10.1016/0960-894x(96)00001-7

  日期：1996.2

  A series of phosphonic and phosphinic acid derivatives of glutathione were synthesized as potential inhibitors of glutathionylspermidine synthetase, an essential enzyme in the biosynthesis of trypanothione in trypanosomatids. The compounds showed moderate activity.
• Exploitation of Subtilisin BPN‘ as Catalyst for the Synthesis of Peptides Containing Noncoded Amino Acids, Peptide Mimetics and Peptide Conjugates
  作者：Wilna J. Moree、Pamela Sears、Katsuhiro Kawashiro、Krista Witte、Chi-Huey Wong

  DOI：10.1021/ja964399w

  日期：1997.4.1

  The ability of the serine protease subtilisin BPN' to catalyze peptide bond formation between fragments containing noncoded amino acids, peptide mimetics, and peptide conjugates in a kinetic approach was explored. It was found that the enzyme accepts numerous of these types of compounds both as acyl donor and acyl acceptor. The results together with specificity studies reported by others provide an active site model as a guideline in the design of enzymatic synthesis of biologically important compounds.