p-dimethylaminoethoxypropiophenone | 46731-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-dimethylaminoethoxypropiophenone
• 英文别名: 1-(4-(2-(dimethylamino)ethoxy)phenyl)propan-1-one；4-(2-Dimethylamino-ethoxy)-propiophenon；p-(2-Dimethylaminoaethoxy)propiophenon；1-[4-(2-Dimethylamino-aethoxy)-phenyl]-propan-1-on；1-[4-[2-(Dimethylamino)ethoxy]phenyl]propan-1-one
• CAS: 46731-02-6
• 化学式: C₁₃H₁₉NO₂
• mdl: MFCD09943764
• 分子量: 221.299
• InChiKey: VXBVLTCCIAYZCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  亚硝酸丁酯 、 p-dimethylaminoethoxypropiophenone 在 盐酸 、 乙醚 、 乙醇 作用下， 生成 1-[4-(2-dimethylamino-ethoxy)-phenyl]-propane-1,2-dione-2-oxime ; hydrochloride
  参考文献：
  名称：

  1-[(2-Dialkylaminoethoxy)phenyl]-2-amino-1-propanols

  摘要：

  DOI：

  10.1021/jo01357a006
• 作为产物：
  描述：

  二甲氨基氯乙烷盐酸 、 4-羟基苯丙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以83%的产率得到p-dimethylaminoethoxypropiophenone
  参考文献：
  名称：

  Flexible Estrogen Receptor Modulators:  Design, Synthesis, and Antagonistic Effects in Human MCF-7 Breast Cancer Cells

  摘要：

  Although many series of estrogen receptor antagonists continue to be produced, the majority are direct structural analogues of existing modulators. To examine the tolerance of the estrogen receptor toward flexible ligands, a series of novel flexible estrogen receptor antagonists were prepared and their antiproliferative effects on human MCF-7 breast tumor cells investigated. Each of these compounds deviated from the traditional triphenylethylene backbone associated with common tamoxifen analogues through the introduction of a flexible methylene (benzylic) spacing group between one of the aryl rings and the ethylene group and through variations in the basic side chain moiety. The compounds prepared, when assayed in conjunction with a tamoxifen standard, demonstrated high potency in antiproliferative assays against an MCF-7 human breast cancer cell line with low cytotoxicity and high binding affinity. A computational study was undertaken to investigate the compounds ' potential interactions with specific residues within the human estrogen receptor a ligand-binding domain (ER-LBD), predicting these compounds bind in an antiestrogenic fashion within the ER-LBD and interact with those important residues previously identified in the structures of ER-LBD agonist/antagonist cocrystals. These compounds further illustrate the eclectic nature of the estrogen receptor in terms of ligand flexibility tolerance.

  DOI：

  10.1021/jm001119l

文献信息

• SnCl4–Zn: a novel reductive system for deoxygenative coupling of aliphatic, aromatic, chalcone epoxide, and indanone carbonyl compounds to olefins
  作者：Gulab Khushalrao Pathe、Naseem Ahmed

  DOI：10.1016/j.tetlet.2015.01.194

  日期：2015.3

  SnCl4–Zn complex provided a novel reductive system in the deoxygenative cross-coupling of aliphatic, aromatic, chalcone epoxide and indanone carbonyl compounds to olefins in high yield (55–86%) at reflux temperature in THF. The advantage of this reagent is inexpensive, short reaction time, and high yield compared to the reagents used in the McMurry cross-coupling reaction.

  SnCl 4 -Zn络合物在脂肪族，芳香族，查尔酮环氧化物和茚满酮羰基化合物在THF中回流温度下，以高收率（55-86％）脱氧交叉偶联，提供了一种新颖的还原体系。与用于McMurry交叉偶联反应的试剂相比，该试剂的优点是价格便宜，反应时间短且产率高。
• Anti-proliferative activities of flavone–estradiol Stille-coupling adducts and of indanone-based compounds obtained by SnCl₄/Zn-catalysed McMurry cross-coupling reactions
  作者：Gulab Khushalrao Pathe、Naveen K. Konduru、Iram Parveen、Naseem Ahmed

  DOI：10.1039/c5ra15685h

  日期：——

  Flavone–estradiol adducts and indanophen based tamoxifen analogs are synthesized using SnCl₄–Zn reagent via McMurry reaction and evaluated in human cervical (HeLa) and breast cancer cells (MCF-7 and MDA-MB-231) for the anti-proliferative activity.

  使用SnCl₄–Zn试剂通过McMurry反应合成黄酮-雌二醇加合物和基于indanophen的他莫昔芬类似物，并在人宫颈癌（HeLa）和乳腺癌细胞（MCF-7和MDA-MB-231）中评估其抗增殖活性。
• Non-steroidal modulators of estrogen receptors
  申请人：——

  公开号：US20020161007A1

  公开（公告）日：2002-10-31

  Estrogen receptor modulators, compositions comprising the compounds and methods relating to the use thereof are described. The compounds may be used in inhibiting the proliferation of and/or induces apoptosis in human breast cancer cells.

  本文描述了雌激素受体调节剂，包括该化合物的组合物和使用方法。该化合物可用于抑制人乳腺癌细胞的增殖和/或诱导凋亡。
• Casadio; Pala; Crescenzi, Arzneimittel-Forschung/Drug Research, 1966, vol. 16, # 5, p. 592 - 596
  作者：Casadio、Pala、Crescenzi、Marazzi-Uberti、Fresia

  DOI：——

  日期：——
• Flexible Estrogen Receptor Modulators:  Design, Synthesis, and Antagonistic Effects in Human MCF-7 Breast Cancer Cells
  作者：Mary J. Meegan、Rosario B. Hughes、David G. Lloyd、D. Clive Williams、Daniela M. Zisterer

  DOI：10.1021/jm001119l

  日期：2001.3.1

  Although many series of estrogen receptor antagonists continue to be produced, the majority are direct structural analogues of existing modulators. To examine the tolerance of the estrogen receptor toward flexible ligands, a series of novel flexible estrogen receptor antagonists were prepared and their antiproliferative effects on human MCF-7 breast tumor cells investigated. Each of these compounds deviated from the traditional triphenylethylene backbone associated with common tamoxifen analogues through the introduction of a flexible methylene (benzylic) spacing group between one of the aryl rings and the ethylene group and through variations in the basic side chain moiety. The compounds prepared, when assayed in conjunction with a tamoxifen standard, demonstrated high potency in antiproliferative assays against an MCF-7 human breast cancer cell line with low cytotoxicity and high binding affinity. A computational study was undertaken to investigate the compounds ' potential interactions with specific residues within the human estrogen receptor a ligand-binding domain (ER-LBD), predicting these compounds bind in an antiestrogenic fashion within the ER-LBD and interact with those important residues previously identified in the structures of ER-LBD agonist/antagonist cocrystals. These compounds further illustrate the eclectic nature of the estrogen receptor in terms of ligand flexibility tolerance.