(L,D)-diphenyl 1-aminoethylphosphonate | 73270-41-4

• 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: (L,D)-diphenyl 1-aminoethylphosphonate
• 英文别名: Diphenyl 1-aminoethanphosphonat；Phosphonic acid, (1-aminoethyl)-, diphenyl ester；1-diphenoxyphosphorylethanamine
• CAS: 73270-41-4
• 化学式: C₁₄H₁₆NO₃P
• 分子量: 277.26
• InChiKey: MDPJOJBNZKKURJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (L,D)-diphenyl 1-aminoethylphosphonate 在 10% palladium on active carbon 氢气 、 氯甲酸乙酯 、 三乙胺 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 0.83h， 生成 (2S)-2-amino-N-(1-diphenoxyphosphorylethyl)propanamide
  参考文献：
  名称：

  Transesterification of Diphenyl Phosphonates using the Potassium Fluoride/Crown Ether/Alcohol System; Part 2. The Use of Diphenyl 1-Aminoalkanephosphonates in Phosphonopeptide Synthesis

  摘要：

  DOI：

  10.1055/s-1982-29818
• 作为产物：
  描述：

  亚磷酸三苯酯 在 碘代三甲硅烷 作用下， 以 溶剂黄146 为溶剂， 生成 (L,D)-diphenyl 1-aminoethylphosphonate
  参考文献：
  名称：

  Moriarty, Robert M.; Liu, Kaiming; Tuladhar, Sudersan M., Phosphorus, Sulfur and Silicon and the Related Elements, 1996, vol. 109, # 1-4, p. 237 - 240

  摘要：

  DOI：

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。
• Serine peptidase modulators
  申请人：——

  公开号：US20020061839A1

  公开（公告）日：2002-05-23

  The present invention relates to new compounds having modulatory (inhibitory and stimulatory) activity on serine peptidases and proteases in general and dipeptidyl peptidase IV, prolyl oligopeptidase (PO), dipeptidyl peptidase II (DPP II), fibroblast activation protein &agr; (FAP&agr;), lysosomal Pro—X carboxypeptidase and elastase in particular. These new compounds can be used for the treatment of a variety of disease states in which these peptidases are involved.

  本发明涉及一种对丝氨酸蛋白酶和蛋白酶（包括二肽基肽酶IV、脯氨酰寡肽酶（PO）、二肽基肽酶II（DPP II）、成纤维细胞活化蛋白α（FAPα）、溶酶体Pro-X羧肽酶和弹性蛋白酶）具有调节（抑制和刺激）活性的新化合物。这些新化合物可用于治疗各种与这些肽酶有关的疾病状态。
• SYNTHESIS OF O,O-DIPHENYL [SUBSTITUTED (2-SELENOMORPHOLIN-4-YL-ACETYL AMINO)] ALKYL PHOSPHONATES
  作者：Liming Hu、Zhiyuan Chen、Shengmei Lu、Xueshu Li、Zhaojie Liu、Hansheng Xu

  DOI：10.1080/10426500490459687

  日期：2004.6

  A series of O,O-diphenyl [substituted (2-selenomorpholin-4-yl-acetyl amino)] alkyl phosphonates were synthesized by the reactions of selenomorpholine with O,O-diphenyl 2-chloro- acetylamino alkyl phosphonates. The structures of all new compounds have been confirmed by H-1 NMR, P-31 NMR, IR spectroscopy, Mass spectroscopy and elemental analyses.
• 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.
• Kafarski, Pawel; Lejczak, Barbara; Szewczyk, Jerzy, Canadian Journal of Chemistry, 1983, vol. 61, p. 2425 - 2430
  作者：Kafarski, Pawel、Lejczak, Barbara、Szewczyk, Jerzy

  DOI：——

  日期：——