diphenyl 1-amino-2-methylpropylphosphonate | 73270-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diphenyl 1-amino-2-methylpropylphosphonate
• 英文别名: Diphenyl 1-amino-2-methylpropanphosphonat；Diphenyl (1-amino-2-methylpropyl)phosphonate；1-diphenoxyphosphoryl-2-methylpropan-1-amine
• CAS: 73270-42-5
• 化学式: C₁₆H₂₀NO₃P
• 分子量: 305.313
• InChiKey: OFQJMBVXCZFBPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diphenyl 1-amino-2-methylpropylphosphonate 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 72.0h， 生成 [(3R,4R)-4-benzoyloxy-1-[(1S)-1-diphenoxyphosphoryl-2-methylpropyl]-2,5-dioxopyrrolidin-3-yl] benzoate
  参考文献：
  名称：

  Kafarski, Pawel; Lejczak, Barbara; Szewczyk, Jerzy, Canadian Journal of Chemistry, 1983, vol. 61, p. 2425 - 2430

  摘要：

  DOI：
• 作为产物：
  描述：

  亚磷酸三苯酯 在 palladium 10% on activated carbon 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 diphenyl 1-amino-2-methylpropylphosphonate
  参考文献：
  名称：

  用于检测炎症期间丝氨酸蛋白酶活性的基于荧光二苯基膦酸盐的探针

  摘要：

  基于活性的探针是以活性依赖性方式共价结合蛋白酶活性位点的小分子。我们合成并表征了两种基于荧光活性的探针，它们靶向具有胰蛋白酶样或弹性蛋白酶样活性的丝氨酸蛋白酶。我们评估了这些探针对重组酶的选择性和效力，并证明虽然它们在体外有效标记复杂蛋白质混合物中的活性蛋白酶，但它们在体内的价值较低。学习。我们使用这些探针来评估两种急性炎症小鼠模型（包括胰腺炎和结肠炎）中的丝氨酸蛋白酶活性。正如预期的那样，胰蛋白酶样蛋白酶的活性在胰腺炎期间增加。无论是健康的还是发炎的，胰腺裂解物和结肠腔液中的弹性蛋白酶样蛋白酶水平都很低。外源添加的重组中性粒细胞弹性蛋白酶在与这些样品孵育后受到抑制，与对照相比，这种效果在发炎样品中得到增强。这些数据表明内源性抑制剂和弹性蛋白酶降解蛋白酶在炎症过程中被上调。

  DOI：

  10.1016/j.bmcl.2016.11.064

文献信息

• N-(Phosphonoacetyl)amino phosphonates. Phosphonate analogs of N-(phosphonoacetyl)-L-aspartic acid (PALA)
  作者：Pawel Kafarski、Barbara Lejczak、Przemyslaw Mastalerz、Danuta Dus、Czeslaw Radzikowski

  DOI：10.1021/jm00149a002

  日期：1985.11

  Michaelis-Arbuzov reaction of N-(chloroacetyl)amino phosphonic acids or their esters, followed by acidolysis, gives moderate yields of N-(phosphonoacetyl) derivatives of a variety of (aminoalkyl)phosphonic acids, including analogues of the cytostatic agent PALA, in which the alpha- or beta-carboxylic groups in the aspartate moiety are replaced by a PO3H2 function. Assay of cytostatic activity with

  N-（氯乙酰基）氨基膦酸或其酯的Michaelis-Arbuzov反应，然后酸解，可得到中等收率的各种（氨基烷基）膦酸的N-（膦酰基乙酰基）衍生物，包括细胞抑制剂PALA的类似物。天冬氨酸部分中的α-或β-羧基被PO3H2取代。用人KB细胞系的细胞抑制活性的测定表明，用PO 3 H 2取代PALA中的任何COOH基团会导致细胞抑制活性的完全丧失。在该报告中描述的其他[N-（膦酰基乙酰基）氨基]烷基膦酸的情况下也未观察到活性。
• Remote Binding Energy in Antibody Catalysis:  Studies of a Catalytically Unoptimized Specificity Pocket
  作者：Herschel Wade、Thomas S. Scanlan

  DOI：10.1021/ja983017e

  日期：1999.2.1

  Binding interactions remote from the hydrolytic reaction center have been probed with substrate and phosphonate transition state analogues to understand how these types of interactions are used to promote catalysis in the 17E8 system, We find that the hapten-generated recogniton pocket in 17E8 has properties that are analogous to those of specificity pockets in enzymes, pie have also found that there are specific requirements to form catalytically productive interactions between the side chain and the recognition pocket including conformation, size, and geometry. An additional requirement includes Favorable simultaneous interactions between the side chain and binding packet along with favorable interactions with the oxyanion hole. The 17E8 side chain recognition pocket seems to be less catalytically efficient than analogous pockets in enzymatic systems. The apparent binding energy gained from the methylene-packet interactions in the 17E8 system is significantly smaller than those observed in natural enzymes. Furthermore, 17E8 does not use specific interactions in the recognition pocket to significantly affect catalytic turnover (k(cat)) which is thought to be a trait of an unoptimized catalyst. Analysis of the crystal structure of the 17E8,hapten complex has allowed for the identification of differences between the active sites of 17E8; and several proteases, The identified differences give insight to the sources of the inefficient use of binding energy.
• Diphenyl 1-Aminoalkanephosphonates
  作者：Józef Oleksyszyn、Lidia Subotkowska、Przemysław Mastalerz

  DOI：10.1055/s-1979-28903

  日期：——
• Transesterification of Diphenyl Phosphonates using the Potassium Fluoride/Crown Ether/Alcohol System; Part 2. The Use of Diphenyl 1-Aminoalkanephosphonates in Phosphonopeptide Synthesis
  作者：Barbara Lejczak、Paweł Kafarski、Jerzy Szewczyk

  DOI：10.1055/s-1982-29818

  日期：——
• OLEKSYSZYN J.; SUBOTKOWSKA L.; MASTALERZ P., SYNTHESIS, 1979, NO 12, 985-986
  作者：OLEKSYSZYN J.、 SUBOTKOWSKA L.、 MASTALERZ P.

  DOI：——

  日期：——