1,4-bis(4-methoxyphenyl)azetidin-2-one | 123003-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1,4-bis(4-methoxyphenyl)azetidin-2-one
• CAS: 123003-83-8
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: LVHFYZBCAGFJQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-bis(4-methoxyphenyl)azetidin-2-one 、 碘甲烷 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.83h， 以59%的产率得到trans-1,4-bis(4-methoxyphenyl)-3-methylazetidin-2-one
  参考文献：
  名称：

  一般通用的3-苯基硫基β-内酰胺类化合物作为3-甲基-2-氮杂环丁烷酮的先导分子的合成

  摘要：

  在所述反应条件下，使用三氯氧化磷和苯磺酰氯的乙胺-亚胺环加成反应以良好的收率得到反式3-苯硫基2-氮杂环丁烷酮。最后使用阮内镍进行脱硫和烷基化，以立体选择性方式得到反式3-甲基-2-氮杂环丁烷酮。

  DOI：

  10.1002/jhet.5570440523
• 作为产物：
  描述：

  甲氧苯胺 在 三甲基氯硅烷 、 锌 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.78h， 生成 1,4-bis(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  β-Lactam Estrogen Receptor Antagonists and a Dual-Targeting Estrogen Receptor/Tubulin Ligand

  摘要：

  Twelve novel beta-lactams were synthesized and their antiproliferative effects and binding affinity for the predominant isoforms of the estrogen receptor (ER), ER alpha and ER beta, were determined. beta-Lactams 23 and 26 had the strongest binding affinities for ER alpha (IC50 values: 40 and 8 nM, respectively) and ER beta (IC50 values: 19 and 15 nM). beta-Lactam 26 was the most potent in antiproliferative assays using MCF-7 breast cancer cells, and further biochemical analysis showed that it caused accumulation of cells in G(2)/M phase (mitotic blockade) and depolymerization of tubulin in MCF-7 cells. Compound 26 also induced apoptosis and downregulation of the expression of pro-survival proteins Bcl-2 and Mcl-1. Computational modeling predicted binding preferences for the dual ER/tubulin ligand 26. This series is an important addition to the known pool of ER antagonists and beta-lactam 26 is the first reported compound that has dual-targeting properties for both the ER and tubulin.

  DOI：

  10.1021/jm500670d

文献信息

• Chemoselective Synthesis of β-Amino Ester or β-Lactam via Sonochemical Reformatsky Reaction
  作者：Adam Shih-Yuan Lee、Yu-Ting Chang、Feng-Yi Su

  DOI：10.1002/jccs.201300308

  日期：2014.2

  A series of β‐amino esters were synthesized by the reaction of N‐tosyl aldimine or N‐hydroxy aldimine with bromoacetate by sonochemical Reformatsky reaction. The β‐N‐hydroxyamino ester was obtained and the formed sensitive hydroxylamino functionality was resistant under the reaction condition. The β‐lactam also was synthesized by the reaction of N‐p‐methoxy aldimine as reacting substrate under this

  N-甲苯磺酰胺或N-羟醛胺与溴乙酸酯通过声化学Reformatsky反应合成了一系列β-氨基酯。获得了β- N-羟氨基酯，并且在反应条件下形成的敏感羟氨基官能团具有抗性。的β内酰胺也由反应合成Ñ - p -甲氧基醛亚胺作为底这个声化学的Reformatsky反应条件下反应。
• The Reformatskii type reaction of Gilman and Speeter in the preparation of valuable .beta.-lactams in carbapenem synthesis: scope and synthetic utility
  作者：Claudio Palomo、Fernando P. Cossio、Ana Arrieta、Jose M. Odriozola、Mikel Oiarbide、Jesus M. Ontoria

  DOI：10.1021/jo00285a021

  日期：1989.11
• PALOMO, CLAUDIO;COSSIO, FERNANDO P.;ARRIETA, ANA;ODRIOZOLA, JOSE M.;OIARB+, J. ORG. CHEM., 54,(1989) N4, C. 5736-5745
  作者：PALOMO, CLAUDIO、COSSIO, FERNANDO P.、ARRIETA, ANA、ODRIOZOLA, JOSE M.、OIARB+

  DOI：——

  日期：——
• A general and versatile synthesis of 3-phenylthio β-lactams as lead molecules for 3-methyl-2-azetidinones
  作者：Seema Kanwar、S. D. Sharma

  DOI：10.1002/jhet.5570440523

  日期：2007.9

  Ketene-imine cycloaddition using phosphorus oxychloride and benzenesulfonyl chloride under the described reaction conditions yielded trans 3-phenylthio 2-azetidinones in good yields. Desulfurization using Raney nickel and alkylation finally afforded trans 3-methyl-2-azetidinones in a stereoselective manner.

  在所述反应条件下，使用三氯氧化磷和苯磺酰氯的乙胺-亚胺环加成反应以良好的收率得到反式3-苯硫基2-氮杂环丁烷酮。最后使用阮内镍进行脱硫和烷基化，以立体选择性方式得到反式3-甲基-2-氮杂环丁烷酮。
• β-Lactam Estrogen Receptor Antagonists and a Dual-Targeting Estrogen Receptor/Tubulin Ligand
  作者：Niamh M. O’Boyle、Jade K. Pollock、Miriam Carr、Andrew J. S. Knox、Seema M. Nathwani、Shu Wang、Laura Caboni、Daniela M. Zisterer、Mary J. Meegan

  DOI：10.1021/jm500670d

  日期：2014.11.26

  Twelve novel beta-lactams were synthesized and their antiproliferative effects and binding affinity for the predominant isoforms of the estrogen receptor (ER), ER alpha and ER beta, were determined. beta-Lactams 23 and 26 had the strongest binding affinities for ER alpha (IC50 values: 40 and 8 nM, respectively) and ER beta (IC50 values: 19 and 15 nM). beta-Lactam 26 was the most potent in antiproliferative assays using MCF-7 breast cancer cells, and further biochemical analysis showed that it caused accumulation of cells in G(2)/M phase (mitotic blockade) and depolymerization of tubulin in MCF-7 cells. Compound 26 also induced apoptosis and downregulation of the expression of pro-survival proteins Bcl-2 and Mcl-1. Computational modeling predicted binding preferences for the dual ER/tubulin ligand 26. This series is an important addition to the known pool of ER antagonists and beta-lactam 26 is the first reported compound that has dual-targeting properties for both the ER and tubulin.