二苯基氨基甲基膦酸酯 | 34002-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 二苯基氨基甲基膦酸酯
• 英文名称: diphenyl aminomethylphosphonate
• 英文别名: diphenyl (aminomethyl)phosphonate；phenyl aminomethylphosphonate；diphenoxyphosphorylmethanamine
• CAS: 34002-94-3
• 化学式: C₁₃H₁₄NO₃P
• 分子量: 263.233
• InChiKey: RLRLWECTYYJXST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  二苯基氨基甲基膦酸酯 在 双(三甲基硅烷基)氨基钾 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl N-[1-diphenoxyphosphoryl-2-(1H-indol-3-yl)ethyl]carbamate
  参考文献：
  名称：

  Synthesis of diphenyl phosphonate analogues of tyrosine and tryptophan and derived peptides as chymotrypsin inhibitors

  摘要：

  报告了酪氨酸和色氨酸的 α-氨基膦酸盐类似物（如 4 和 5）的合成及其与含脯氨酸二肽的结合；在合成的序列中，二肽 Z-Pro-TrpP(OPh)2 是唯一的衍生物。在合成的序列中，Z-Pro-TrpP(OPh)2 是唯一一种可作为丝氨酸蛋白酶糜蛋白酶不可逆灭活剂的衍生物，相反，酪氨酸类似物 4 是该酶的竞争性可逆抑制剂，而色氨酸类似物 5 则是一种慢结合抑制剂。

  DOI：

  10.1039/cc9960001155
• 作为产物：
  描述：

  亚磷酸三苯酯 在 氢溴酸 、 溶剂黄146 作用下， 反应 5.5h， 生成 二苯基氨基甲基膦酸酯
  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

• [EN] BROAD SPECTRUM ANTIBIOTIC ARYLOMYCIN ANALOGS<br/>[FR] ANALOGUES DE L'ARYLOMYCINE À SPECTRE ANTIBIOTIQUE LARGE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2013138187A1

  公开（公告）日：2013-09-19

  Arylomycin analogs are provided, wherein the analogs can have broad spectrum bioactivity. Resistance to the antibiotic bioactivity of natural product arylomycin in a range of pathogenic bacterial species has been found to depend upon single amino acid mutations at defined positions of bacterial Signal Peptidases (SPases), wherein the presence of a proline residue confers arylomycin resistance. Arylomycin analogs are provided herein that can overcome that resistance and provide for a broader spectrum of antibiotic bioactivity than can natural product arylomycins such as arylomycin A2. Methods for determining if a bacterial strain is susceptible to narrow spectrum arylomycin antibiotics, or if a broad spectum analog is required for treatment, is provided. Pharmaceutical compositions and methods of treatment of bacterial infections, and methods of synthesis of arylomycin analogs, are provided.

  提供了芳基霉素类似物，其中这些类似物可以具有广谱生物活性。已发现在一系列致病性细菌物种中，对天然产物芳基霉素的抗生素活性的抗性取决于细菌信号肽酶（SPases）的特定位置的单个氨基酸突变，其中脯氨酸残基的存在赋予了芳基霉素抗性。本文提供了可以克服该抗性并提供比芳基霉素A2等天然产物芳基霉素更广谱抗生素活性的芳基霉素类似物。提供了用于确定细菌菌株是否对窄谱芳基霉素抗生素敏感，或者是否需要广谱类似物进行治疗的方法。提供了用于治疗细菌感染的药物组合物和方法，以及芳基霉素类似物的合成方法。
• Cephalosporin compounds
  申请人：Merck & Co., Inc.

  公开号：US03962224A1

  公开（公告）日：1976-06-08

  Novel 7-azido-3-cephem compounds are prepared via .alpha.-amino-phosphonoacetate esters. The cephem compounds are intermediates for the preparation of novel and known useful antibiotic cephalosporins.

  通过α-氨基-磷酸酯酯制备新型7-偶氮基-3-头孢烯化合物。这些头孢烯化合物是制备新型和已知有用的抗生素头霉素的中间体。
• 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。
• N-Phosphonomethylglycinonitrile and certain derivatives thereof
  申请人：Monsanto Company

  公开号：US04221583A1

  公开（公告）日：1980-09-09

  N-phosphonomethylglycinonitrile and certain derivatives thereof are novel compounds which can be used as herbicides themselves and/or can be converted to known herbicides. Such novel compounds, and others, can be prepared by a novel process.

  N-磷酸甲基甘氨酸腈及其某些衍生物是一种新型化合物，可用作除草剂本身和/或可转化为已知的除草剂。这种新型化合物和其他化合物可以通过一种新型工艺制备。
• A convenient synthesis ofN-t-butyl-N?-aminocarbonyl-N-(substituted)benzoyl-hydrazine containing?-aminoalkylphosphonate groups in a one-pot procedure
  作者：Qingmin Wang、Zaiguo Li、Runqiu Huang、Junran Cheng

  DOI：10.1002/hc.3

  日期：——

  for the synthesis of α-isocyanatoalkylphosphonates enjoys a number of advantages: the reaction is carried out under mild condition in good yield, triphosgene is relatively safe to handle because of its low vapor pressure and high stability, and the experimental procedure is simple. This method can be applicable to the synthesis of other α-isocyanatoalkyl-phosphonates and urylenediphosphonates. The structures

  合成了多种含有α-氨基烷基膦酸酯基团的新型N-叔丁基-N'-氨基羰基-N-（取代）苯甲酰肼。用三光气处理α-氨基烷基膦酸酯产生α-异氰酸根合烷基膦酸酯，随后加入N-叔丁基-N-取代的苯甲酰肼，在一锅法中以良好的收率提供标题化合物。三光气介导合成α-异氰酸根合烷基膦酸酯的反应具有许多优点：反应条件温和，产率高，三光气蒸汽压低，稳定性高，操作相对安全，实验步骤很简单。该方法可适用于合成其他α-异氰酸根合烷基膦酸酯和亚脲基二膦酸酯。所有产物和副产物的结构均通过1H NMR、31P NMR、IR和质谱以及元素分析证实。我们还发现一些化合物具有潜在的抗烟草花叶病毒 (TMV) 活性和抗癌活性。© 2001 John Wiley & Sons, Inc. 杂原子化学 12:68–72, 2001