diphenyl <1-(1-amino)pentyl>phosphonate | 156336-41-3

• 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)pentyl>phosphonate
• 英文别名: diphenyl [1-(1-amino)pentyl]phosphonate；Diphenyl (1-aminopentyl)phosphonate；1-diphenoxyphosphorylpentan-1-amine
• CAS: 156336-41-3
• 化学式: C₁₇H₂₂NO₃P
• 分子量: 319.34
• InChiKey: CTOWVYVHRPJNAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  426.5±37.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  N-邻苯二甲酰甘氨酰氯 、 diphenyl <1-(1-amino)pentyl>phosphonate 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以48%的产率得到diphenyl(N-phthalimidomethylcarbonyl)aminomethyl(n-butyl) phosphonate
  参考文献：
  名称：

  熊果酸及其同系物的膦酰二肽缀合物的合成

  摘要：

  为了制备具有不寻常性质和广谱活性的天然生物活性 3β-羟基-urs-12-en-28-oic酸（熊果酸）的新型衍生物，进行了许多化学反应。首先，以三组分曼尼希型反应为关键步骤，通过一系列反应制备了多种α-氨基膦酸酯。其次，通过多步反应合成了一系列膦酰二肽及其同系物，包括邻苯二甲酸酐与甘氨酸或β-丙氨酸的缩合、N-封闭氨基酸的氯化、酰氯与α-氨基膦酸酯的偶联和连续肼解。最后，通过 3β-乙酰氧基-urs-12-en-28-oyl 氯与膦酰二肽及其同系物的缩合，获得了新类别的熊果酸及其同系物的膦酰二肽缀合物。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:55–65, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20396

  DOI：

  10.1002/hc.20396
• 作为产物：
  描述：

  diphenyl <1-(1-N-benzyloxycarbonylamino)pentyl>phosphonate 在 氢溴酸 、 溶剂黄146 作用下， 反应 1.5h， 生成 diphenyl <1-(1-amino)pentyl>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。
• Inhibitors and substrates of thrombin
  申请人：THROMBOSIS RESEARCH INSTITUTE

  公开号：EP0807638A1

  公开（公告）日：1997-11-19

  Peptides which act as inhibitors or substrates of thrombin are derived from the formula: Aa1 is wherein Ar1 and Ar2 are the same or different and are selected from naphthyl, thionaphthyl, indolyl and saturated groups corresponding to these, optionally substituted by up to three groups from C1-C3 alkyl and C1-C3 alkoxy, L1 and L2 are the same or different and are selected from CH2, CH2-CH2, O-CH2 and S-CH2, or Ar-L is H, diphenylmethyl, fluorenyl or saturated groups corresponding to these, provided that both Ar-L groups are not H; and Aa2 is or its C1-C3 alkyl substituted derivatives, wherein R8 is CH2, CH2-CH2, S-CH2, S-C(CH3)2 or CH2-CH2-CH2, provided that when Aa1 is naphthylalanine Y is C3-C9 alkyl or C5-C10 aryl or C5-C10 alkylaryl optionally substituted by up to three groups selected from hydroxy and C1-C4 alkoxy.

  可作为凝血酶抑制剂或底物的肽类由以下公式衍生而来： Aa1 是 其中 Ar1 和 Ar2 相同或不同，选自萘基、硫萘基、吲哚基和与这些基团相对应的饱和基团，可选择被最多三个来自 C1-C3 烷基和 C1-C3 烷氧基的基团取代、 L1 和 L2 相同或不同，选自 CH2、 - 、O- 和 S- 、 或 Ar-L 为 H、二苯甲基、芴基或与之相对应的饱和基团，但两个 Ar-L 基团均非 H；以及 Aa2 是 或其 C1-C3 烷基取代衍生物、 其中 R8 为 、 - 、S- 、S-C(CH3)2 或 - - ，条件是当 Aa1 为萘丙氨酸时，Y 为 C3-C9 烷基或 C5-C10 芳基或 C5-C10 烷芳基，最多可任选被三个选自羟基和 C1-C4 烷氧基的基团取代。
• Kinetic and Mechanistic Characterization of an Efficient Hydrolytic Antibody: Evidence for the Formation of an Acyl Intermediate
  作者：Jincan Guo、Wei Huang、Thomas S. Scanlan

  DOI：10.1021/ja00093a002

  日期：1994.7
• INHIBITORS AND SUBSTRATES OF THROMBIN
  申请人：THROMBOSIS RESEARCH INSTITUTE

  公开号：EP0509080A1

  公开（公告）日：1992-10-21
• US6387881B1
  申请人：——

  公开号：US6387881B1

  公开（公告）日：2002-05-14