diethyl (5-(1,3-dioxoisoindolin-2-yl)pentyl)phosphonate | 145119-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: diethyl (5-(1,3-dioxoisoindolin-2-yl)pentyl)phosphonate
• 英文别名: diethyl 5-(1,3-dioxoisoindolin-2-yl)pentylphosphonate；[5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentyl]-phosphonic acid diethyl ester；2-(5-diethoxyphosphorylpentyl)isoindole-1,3-dione
• CAS: 145119-11-5
• 化学式: C₁₇H₂₄NO₅P
• 分子量: 353.355
• InChiKey: WDZCGXLTFLYJPM-UHFFFAOYSA-N

物化性质

• 沸点：
  483.2±28.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (5-(1,3-dioxoisoindolin-2-yl)pentyl)phosphonate 在 肼 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 18.0h， 以72%的产率得到ω-Aminopentyl-phosphorigsaeurediethylester
  参考文献：
  名称：

  [EN] NOVEL THIOPHENE AMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATING COMPLEMENT-MEDIATED DISEASES AND CONDITIONS
  [FR] NOUVELLES AMIDINES DE THIOPHENE, COMPOSITIONS DE CES AMIDINES ET PROCEDE POUR TRAITER DES MALADIES ET DES ETATS MEDIES PAR LE COMPLEMENT

  摘要：

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用化合物I的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本规范中定义的芳香族或杂环芳基。

  公开号：

  WO2003099805A1
• 作为产物：
  描述：

  1,5-二溴戊烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 diethyl (5-(1,3-dioxoisoindolin-2-yl)pentyl)phosphonate
  参考文献：
  名称：

  氨基膦酸锆手性Salen Mn(III)配合物的合成及α-甲基苯乙烯催化不对称环氧化反应的研究

  摘要：

  通过与不同连接臂长度 (CH2) n (n = 2–6) 的轴向配位，将手性 Salen Mn (III) 复合物固定在氨基膦酸锆上，从而得到一系列非均相催化剂。该催化剂在α-甲基苯乙烯的不对称环氧化反应中表现出良好的催化效率。一种 n = 6 的多相催化剂在 NaClO/PPNO 体系中比原始手性 salen Mn (III) 络合物具有更高的催化性能。它可以很容易地回收和重复使用多次，而不会显着损失活性。

  DOI：

  10.3184/174751912x13408679046933

文献信息

• Novel thiophene amidines, compositions thereof, and methods of treating complement-mediated diseases and conditions
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US20040009995A1

  公开（公告）日：2004-01-15

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula I 1 or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R 1 , R 2 , R 3 , R 4 and R 7 are defined in the specification, Z is SO or SO 2 , and Ar is an aromatic or heteroaromatic group as defined herein.

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用公式I的化合物的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中在规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本文中定义的芳香族或杂环芳基。
• Chemoselective Activation of Diethyl Phosphonates: Modular Synthesis of Biologically Relevant Phosphonylated Scaffolds
  作者：Pauline Adler、Amandine Pons、Jing Li、Jörg Heider、Bogdan R. Brutiu、Nuno Maulide

  DOI：10.1002/anie.201806343

  日期：2018.10

  Phosphonates have garnered considerable attention for years owing to both their singular biological properties and their synthetic potential. State‐of‐the‐art methods for the preparation of mixed phosphonates, phosphonamidates, phosphonothioates, and phosphinates rely on harsh and poorly selective reaction conditions. We report herein a mild method for the modular preparation of phosphonylated derivatives

  多年来，由于其独特的生物学特性和合成潜力，膦酸酯已经引起了相当大的关注。用于制备混合膦酸酯，膦酰胺，膦硫代酸酯和次膦酸酯的最新方法依赖于苛刻且选择性差的反应条件。我们在此报告了一种温和的方法，用于模块化制备膦酰化衍生物，其中一些表现出有趣的生物学活性，其基于三氟甲磺酸酐的化学选择性活化。该程序可以用广泛的O，S，N和C亲核试剂进行灵活甚至重复的取代。
• Synthesis and Characterization of Aminophosphonates Zirconium as New Mesoporous Materials
  作者：Liang Zhou

  DOI：10.1155/2012/640317

  日期：——

  A serial of aminophosphonates zirconium with the different arm lengths of –(CH₂)n– organic chains (n=2–6) was synthesized for the first time. These compounds are characterized by FT-IR, SEM, TEM, TG and nitrogen adsorption-desorption. And based on the experimental data, these materials not only have layer structure mesoporous and good thermal stability such as zirconium phosphate, but also can be adjusted the layer distance, pore size and pore volume. So aminophosphonates zirconium posses special excellent properties and will have potential prospect applications.

  一系列具有不同碳链长度的氨基膦酸锆化合物（n=2-6）首次合成。这些化合物通过FT-IR、SEM、TEM、TG和氮吸附-脱附进行表征。根据实验数据，这些材料不仅具有类似于磷酸锆的层状结构介孔和良好的热稳定性，而且可以调节层间距离、孔径和孔体积。因此，氨基膦酸锆具有特殊的优异性能，并将具有潜在的应用前景。
• Thiophene amidines, compositions thereof, and methods of treating complement-mediated diseases and conditions
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US07138530B2

  公开（公告）日：2006-11-21

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula (I) or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R1, R2, R3, R4 and R7 are defined in the specification, Z is SO or SO2, and Ar is an aromatic or heteroaromatic group as defined herein.

  本发明揭示了一种治疗由补体级联反应的经典途径介导的急性或慢性疾病症状的方法，包括向需要此类治疗的哺乳动物施用公式（I）的化合物或其溶剂化物、水合物或药学上可接受的盐的治疗有效量；其中R1、R2、R3、R4和R7在规范中有定义，Z为SO或SO2，Ar为芳香或杂芳基，如规范中所定义。
• Virtual screening, selection and development of a benzindolone structural scaffold for inhibition of lumazine synthase
  作者：Arindam Talukdar、Ekaterina Morgunova、Jianxin Duan、Winfried Meining、Nicolas Foloppe、Lennart Nilsson、Adelbert Bacher、Boris Illarionov、Markus Fischer、Rudolf Ladenstein、Mark Cushman

  DOI：10.1016/j.bmc.2010.03.072

  日期：2010.5

  Virtual screening of a library of commercially available compounds versus the structure of Mycobacterium tuberculosis lumazine synthase identified 2-(2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamido)acetic acid ( 9) as a possible lead compound. Compound 9 proved to be an effective inhibitor of M. tuberculosis lumazine synthase with a K-i of 70 mu M. Lead optimization through replacement of the carboxymethylsulfonamide sidechain with sulfonamides substituted with alkyl phosphates led to a four-carbon phosphate 38 that displayed a moderate increase in enzyme inhibitory activity (K-i 38 mu M). Molecular modeling based on known lumazine synthase/inhibitor crystal structures suggests that the main forces stabilizing the present benzindolone/enzyme complexes involve pi-pi stacking interactions with Trp27 and hydrogen bonding of the phosphates with Arg128, the backbone nitrogens of Gly85 and Gln86, and the side chain hydroxyl of Thr87. (C) 2010 Elsevier Ltd. All rights reserved.