phenylcarbamoylmethylphosphonic acid diethyl ester | 3699-83-0

• 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: phenylcarbamoylmethylphosphonic acid diethyl ester
• 英文别名: diethyl [2-oxo-(2-phenylamino)ethyl]phosphonate；N-(phenyl)diethylphosphonoacetamide；(phenylcarbamoyl-methyl)-phosphonic acid diethyl ester；(Phenylcarbamoyl-methyl)-phosphonsaeure-diaethylester；Diaethoxyphosphoryl-essigsaeure-anilid；Anilinocarbonylmethylphosphonsaeurediaethylester；2-diethoxyphosphoryl-N-phenylacetamide
• CAS: 3699-83-0
• 化学式: C₁₂H₁₈NO₄P
• 分子量: 271.253
• InChiKey: XLSQHDWSRFSZNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  60-63 °C(Solv: ligroine (8032-32-4))
• 沸点：
  174-177 °C(Press: 0.25 Torr)
• 密度：
  1.1842 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenylcarbamoylmethylphosphonic acid diethyl ester 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以48%的产率得到[N-(phenylcarbamoyl)methyl]phosphonic acid
  参考文献：
  名称：

  Plant-growth-regulatingN-(phosphonoacetyl)amines

  摘要：

  AbstractA series of N‐(phosphonacetyl)amine derivatives were synthesized and screened for plant‐growth regulating activity on Lepidium sativum L. and Cucumis sativus L. Aromatic N‐(phosphonoacetyl)amines. which may be considered as possible analogues of N‐acylaniline herbicides obtained by replacement of their acyl group by the phosphonacetyl moiety, exhibited significant or moderate herbicidal activity. In contrast, N‐(phosphonoacetyl)amino acids and N‐(phosphonoacetyl)aminophosphonic acids promoted the growth of L. sativum and C. sativus roots.

  DOI：

  10.1002/ps.2780400110
• 作为产物：
  描述：

  二乙基膦酰基乙酸叔丁酯 在 五氯化磷 作用下， 以 乙醚 为溶剂， 生成 phenylcarbamoylmethylphosphonic acid diethyl ester
  参考文献：
  名称：

  Bodnarchuk,N.D. et al., Journal of general chemistry of the USSR, 1971, vol. 41, p. 1470 - 1473

  摘要：

  DOI：

文献信息

• Evidence for Partially Bound States in Cooperative Molecular Recognition Interfaces
  作者：Elena Chekmeneva、Christopher A. Hunter、Martin J. Packer、Simon M. Turega

  DOI：10.1021/ja803434z

  日期：2008.12.31

  solvents), all of the interactions are formed in the complex and the fully bound state dominates. In this case, additional binding interactions produce incremental increases in complex stability. However, for weaker H-bonds (small K(H) in polar solvents), the formation of additional interactions does not lead to an increase in the overall stability of the complex, due to the population of partially bound states

  配备四个酰胺 H 键合位点的锌卟啉为合作多点结合相互作用的研究提供了刚性分子受体。使用紫外/可见吸收、(1)H 和 (31)P NMR 光谱以及等温滴定量热法在五种不同的情况下研究了该受体与各种带有零、一个和两个 H 键合位点的吡啶配体的相互作用。溶剂。根据填充不同复合物的集合的结合态分析结果，其中形成零、一个或两个潜在的 H 键相互作用。决定系统行为的关键参数是 H 键相互作用的关联常数 K(H) 和分子内相互作用的有效摩尔浓度 EM 的乘积。在此处报告的系统中，EM 为 0。所有分子内相互作用为 1-1 M。对于强 H 键（非极性溶剂中的大 K(H)），所有相互作用都在复合物中形成，并且完全结合状态占主导地位。在这种情况下，额外的结合相互作用会增加复合物稳定性。然而，对于较弱的 H 键（极性溶剂中的小 K(H)），由于存在部分束缚态，额外相互作用的形成不会导致复合物整体稳定性的增加。
• Phosphonates α-lithies agents de transfert fonctionnel. Preparation de phosphonates α-amides et d'amides α, β-insatures, α-substitues
  作者：M.K. Tay、E. About-Jaudet、N. Collignon、P. Savignac

  DOI：10.1016/s0040-4020(01)89078-5

  日期：——

  strategy), or by condensation of an amide enolate with diethylchlorophosphate (second strategy). Acidic hydrolysis of () or () gives α-amidophosphonate () alkylated or not in the α -position. () and () react with aromatic or aliphatic aldehydes to produce α,β-unsatured secondary or tertiary amides ().

  仲或叔α-氨基膦酸酯的锂化阴离子（）或（）可通过α-膦酰基碳负离子与异氰酸酯或氨基甲酸酯之间的反应制备（第一种策略），或通过酰胺烯酸酯与二乙基氯磷酸酯的缩合制备（第二种策略）。（）或（）的酸水解产生α-氨基膦酸酯（）在α位上烷基化或未烷基化。（）和（）与芳族或脂族醛反应生成α，β-不饱和仲或叔酰胺（）。
• Lead Optimization of Benzoxepin-Type Selective Estrogen Receptor (ER) Modulators and Downregulators with Subtype-Specific ERα and ERβ Activity
  作者：Niamh M. O’Boyle、Irene Barrett、Lisa M. Greene、Miriam Carr、Darren Fayne、Brendan Twamley、Andrew J. S. Knox、Niall O. Keely、Daniela M. Zisterer、Mary J. Meegan

  DOI：10.1021/acs.jmedchem.6b01917

  日期：2018.1.25

  tamoxifen (2a) and fulvestrant (5). Three series of ER-ligands based on the benzoxepin scaffold structure were synthesized: series I containing an acrylic acid, series II with an acrylamide, and series III with a saturated carboxylic acid substituent. These compounds were shown to be high affinity ligands for the ER with nanomolar IC50 binding values. Series I acrylic acid ligands were generally ERα selective

  雌激素受体 α (ERα) 是他莫昔芬 ( 2a ) 和氟维司群 ( 5 )等药物设计的重要目标。合成了三个系列的基于苯并氧杂环酯支架结构的 ER 配体：系列 I 含有丙烯酸，系列 II 具有丙烯酰胺，系列 III 具有饱和羧酸取代基。这些化合物被证明是具有纳摩尔 IC 50结合值的 ER 的高亲和力配体。I 系列丙烯酸配体通常具有 ERα 选择性。特别是化合物13e以苯基五-2,4-二烯酸取代基为特征的研究表明，在 MCF-7 乳腺癌细胞中具有抗增殖和下调 ERα 和 ERβ 表达的作用。有趣的是，从系列 III 中，苯氧基丁酸衍生化合物22不具有抗增殖作用，并且选择性下调 ERβ。进行了苯并恶平配体的对接研究。化合物13e是作为临床相关 SERD 开发的有前景的先导物，而化合物22将成为有助于阐明 ERβ 在癌细胞中作用的有用实验探针。
• Aralkanamidophenyl compounds
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0124791A1

  公开（公告）日：1984-11-14

  This disclosure describes novel substituted aralkanamidobenzoic acids and analogs thereof. These compounds are useful pharmaceutical agents for ameliorating atherosclerosis by inhibiting the formation and development of atherosclerotic lesions in the arterial wall of mammals.

  本公开介绍了新型取代的芳香酰胺基苯甲酸及其类似物。这些化合物可抑制哺乳动物动脉壁动脉粥样硬化病变的形成和发展，是改善动脉粥样硬化的有用药物。
• Synthesis and evaluation of 3-ylideneoxindole acetamides as potent anticancer agents
  作者：Chun-Tang Chiou、Wei-Chun Lee、Jiahn-Haur Liao、Jing-Jy Cheng、Lie-Chwen Lin、Chih-Yu Chen、Jen-Shin Song、Ming-Hsien Wu、Kak-Shan Shia、Wen-Tai Li

  DOI：10.1016/j.ejmech.2015.04.062

  日期：2015.6

  Indirubin, an active component in the traditional Chinese medicine formula Danggui Longhui Wan, shows promising anticancer effects. Meisoindigo is an analog derived from indirubin, which is less toxic and appears to be even more potent against cancer. In considering meisoindigo as a structural template for the development of new drugs, we designed and synthesized a series of 3-ylideneoxindole acetamides as novel anticancer agents. The acetamides were then evaluated for in vitro and in vivo anticancer activities. The 3-ylideneoxindole acetamides were found to have better anticancer activity than was indirubin-3'-oxime in several cancer cell lines and also displayed a spectrum of activity similar to that of the drug candidate roscovitine, a CDK inhibitor. Among the 3-ylideneoxindole acetamides, compound 10 showed particularly good efficacy. Cell cycle analysis further revealed that compound 10 arrested cells in the G1 phase and caused an increase in the sub-G1 population, indicating that the apoptosis pathway had been induced. In addition, exposure of cells to compound 10 led to the upregulation of the cell-cycle regulator cyclin D1, which was sustained at a high level. In contrast, the same compound induced a short-term elevation in the level of cyclin E, which was followed by a rapid decrease and the attenuation of Rb phosphorylation. Furthermore, a docking model suggests that compound 10 binds to the active site of CDK4. In testing the therapeutic potency of compound 10 on CT26-xenografted BALB/c mice, a significant reduction in tumor size comparable to that of cisplatin was found when administrated via the i.p. route. The mice presented no loss of body weight, indicating that this compound possesses low toxicity. In the future, we are planning in vivo investigations of these new active anticancer agents to better elucidate active mechanisms at the cellular level and thus benefit the development of anticancer therapies. (C) 2015 Elsevier Masson SAS. All rights reserved.