diphenyl [1-(1-amino)butyl]phosphonate | 174298-47-6

• 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-(1-amino)butyl]phosphonate
• 英文别名: Diphenyl P-(1-aminobutyl)phosphonate；1-diphenoxyphosphorylbutan-1-amine
• CAS: 174298-47-6
• 化学式: C₁₆H₂₀NO₃P
• 分子量: 305.313
• InChiKey: WTFXSXQLKOBOOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  7
• 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-(1-amino)butyl]phosphonate 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 {1-[2-(Diethoxy-phosphoryl)-acetylamino]-butyl}-phosphonic acid ethyl ester phenyl ester
  参考文献：
  名称：

  N-（膦酰基乙酰基）氨基膦酸酯。N-（膦酰基乙酰基）-L-天冬氨酸（PALA）的膦酸酯类似物。

  摘要：

  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。

  DOI：

  10.1021/jm00149a002
• 作为产物：
  描述：

  benzyl N-[1-(diphenoxyphosphoryl)butyl]carbamate 在 氢溴酸 、 溶剂黄146 作用下， 反应 1.5h， 生成 diphenyl [1-(1-amino)butyl]phosphonate
  参考文献：
  名称：

  Remote Binding Energy in Antibody Catalysis:  Studies of a Catalytically Unoptimized Specificity Pocket

  摘要：

  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.

  DOI：

  10.1021/ja983017e

文献信息

• Synthesis of Ursolic Phosphonate Derivatives as Potential Anti-HIV Agents
  作者：Sheng-Lou Deng、Isabelle Baglin、Mohammed Nour、Oxana Flekhter、Claudio Vita、Christian Cavé

  DOI：10.1080/10426500601088838

  日期：2007.3.15

  In order to search for new anti-tumor and anti-viral agents, a series of α-aminophosphonate conjugates of 3-O-β-acetyl ursolic acid were prepared. Their biological activities as cytotoxic and anti-HIV agents were evaluated. The preliminary bioassays indicate that synthesized compounds 7a–j have anti-HIV activity (targeting HIV-1 gp120 and CD4) and no cytotoxicity on HT-29 cells (human colon adenocarcinoma

  为了寻找新的抗肿瘤和抗病毒药物，制备了一系列 3-O-β-乙酰熊果酸的 α-氨基膦酸盐偶联物。评价了它们作为细胞毒性剂和抗HIV剂的生物活性。初步生物测定表明，合成的化合物 7a-j 具有抗 HIV 活性（靶向 HIV-1 gp120 和 CD4）并且对 HT-29 细胞（人结肠腺癌细胞系）没有细胞毒性。
• OLEKSYSZYN, JOZEF;POWERS, JAMES C., BIOCHEMISTRY, 30,(1991) N, C. 485-493
  作者：OLEKSYSZYN, JOZEF、POWERS, JAMES C.

  DOI：——

  日期：——
• KAFARSKI, P.;LEJCZAK, B.;MASTALERZ, P.;DUS, D.;RADZIKOWSKI, C., J. MED. CHEM., 1985, 28, N 11, 1555-1558
  作者：KAFARSKI, P.、LEJCZAK, B.、MASTALERZ, P.、DUS, D.、RADZIKOWSKI, C.

  DOI：——

  日期：——
• US5543396A
  申请人：——

  公开号：US5543396A

  公开（公告）日：1996-08-06
• US5686419A
  申请人：——

  公开号：US5686419A

  公开（公告）日：1997-11-11