diethyl [5-hydroxy-3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]phosphonate | 1609670-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl [5-hydroxy-3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]phosphonate
• CAS: 1609670-00-9
• 化学式: C₂₀H₂₃N₂O₅P
• 分子量: 402.387
• InChiKey: MZTZEAFJKKIKCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.81
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  diethyl [5-hydroxy-3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]phosphonate 在 L-Selectride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Versatile Synthesis of 4-Methylidenepyrazolidin-3-ones Using a Horner–Wadsworth–Emmons Approach

  摘要：

  A new, versatile method for the synthesis of, so far unknown, variously substituted 4-methylidenepyrazolidin-3-ones as potential cytotoxic agents is described. Target compounds were synthesized from the corresponding 4-diethoxyphosphorylpyrazolidin-3-ones which were used as Horner-Wadsworth-Emmons reagents for the olefination of formaldehyde. 4-Phosphorylpyrazolidin-3-ones were, in turn, obtained starting from the sodium salt of ethyl 2-diethoxyphosphoryl-3-hydroxy-2-propenoate, ethyl 2-acyl-2-diethoxyphosphorylacetates, or 3-methoxy-2-diethoxyphosphorylacrylate and monosubstituted or 1,2-disubstituted hydrazines.

  DOI：

  10.1055/s-0033-1340071
• 作为产物：
  描述：

  苯肼 、 ethyl 2-(diethoxyphosphoryl)-3-(4-methoxyphenyl)-3-oxopropanoate 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 以72%的产率得到diethyl [5-hydroxy-3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]phosphonate
  参考文献：
  名称：

  Design, synthesis and cytotoxic evaluation of 4-methylidenepyrazolidin-3-ones

  摘要：

  Three series of new 4-methylidenepyrazolidin-3-ones with various substitution patterns were synthesized and tested for the cytotoxic activity against two human leukemia cell lines NALM-6 and HL-60 as well as MCF-7 breast cancer cell line. Several obtained methylidenepyrazolidinones exhibited high cytotoxic activity with IC50 values below 10 mu M, mainly against HL-60 leukemia cell line and two of them, 18d,e, displayed IC50 <= 5 mu M, against all tested cell lines. Structure activity relationship studies revealed that the presence of phenyl substituents on both ring nitrogen atoms and vinyl or phenyl substituents in position 5 are crucial for high activity. Selected methylidenepyrazolidinones were also tested on normal human umbilical vein endothelial cells (HUVEC) and pyrazolidinone 18a was found to be 5-fold more toxic against HL-60 than normal cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.029