1-(4-chlorophenyl)-5-(dimethylamino)penta-1,4-dien-3-one | 320416-03-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(4-chlorophenyl)-5-(dimethylamino)penta-1,4-dien-3-one
• CAS: 320416-03-3
• 化学式: C₁₃H₁₄ClNO
• 分子量: 235.713
• InChiKey: QUKRUPURRGVIDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-5-(dimethylamino)penta-1,4-dien-3-one 在 劳森试剂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 5-[2-(4-chlorophenyl)vinyl]thien-2-yl-phenylmethanone
  参考文献：
  名称：

  COX-2中噻吩支架的合成与对接研究

  摘要：

  由原位产生的交叉共轭烯氨基硫酮2和α-溴酮/溴乙酸乙酯反应合成了一系列新的噻吩化合物6a-6l。此外，还描述了从 N,N'-双 [(二甲氨基) 亚甲基] 硫脲 9 的环加成反应合成 1,3-噻嗪 12 和官能化的噻喃 18 杂环。此外，这些化合物 6a-6l 和一些抗炎药 (NSAID) 的结合构象是通过它们在 Cyclooxygenase-2 (COX-2) 酶的活性位点的对接来确定的。

  DOI：

  10.3998/ark.5550190.0012.a05
• 作为产物：
  描述：

  4-氯苯亚甲基丙酮 、 N,N-二甲基甲酰胺二甲基缩醛 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 1-(4-chlorophenyl)-5-(dimethylamino)penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrazole derivatives with anticancer activity

  摘要：

  We synthesized thirty-six novel pyrazole derivatives and studied their antiproliferative activity in human ovarian adenocarcinoma A2780 cells, human lung carcinoma A549 cells, and murine P388 leukemia cells.Four of these substances were selected because of their higher antiproliferative activity and further analyses showed that they were all able to induce apoptosis, although to a different extent. The expression of p53 and p21(waf1), which induce apoptosis and cell cycle arrest, was evaluated by western blot analysis in cells treated with compound 12d.The analysis of the cell cycle showed that all the selected compounds cause a partial G2/M block and the formation of polyploid cells. Furthermore, the four selected compounds were tested for their interaction with the microtubular cytoskeletal system by docking analysis, tubulin polymerization assay and immunofluorescence staining, demonstrating that the compound 12d, unlike the other active derivatives, was able to significantly bind dimers of alpha- and beta-tubulin, probably causing a molecular distortion resulting in the disassembly of microtubules. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.014

文献信息

• Singh, Parvesh; Bisetty, Krishna; Mahajan, Mohinder P., South African Journal of Chemistry, 2009, vol. 62, p. 47 - 55
  作者：Singh, Parvesh、Bisetty, Krishna、Mahajan, Mohinder P.

  DOI：——

  日期：——
• Synthesis and biological evaluation of novel pyrazole derivatives with anticancer activity
  作者：Alessandro Balbi、Maria Anzaldi、Chiara Macciò、Cinzia Aiello、Mauro Mazzei、Rosaria Gangemi、Patrizio Castagnola、Mariangela Miele、Camillo Rosano、Maurizio Viale

  DOI：10.1016/j.ejmech.2011.08.014

  日期：2011.11

  We synthesized thirty-six novel pyrazole derivatives and studied their antiproliferative activity in human ovarian adenocarcinoma A2780 cells, human lung carcinoma A549 cells, and murine P388 leukemia cells.Four of these substances were selected because of their higher antiproliferative activity and further analyses showed that they were all able to induce apoptosis, although to a different extent. The expression of p53 and p21(waf1), which induce apoptosis and cell cycle arrest, was evaluated by western blot analysis in cells treated with compound 12d.The analysis of the cell cycle showed that all the selected compounds cause a partial G2/M block and the formation of polyploid cells. Furthermore, the four selected compounds were tested for their interaction with the microtubular cytoskeletal system by docking analysis, tubulin polymerization assay and immunofluorescence staining, demonstrating that the compound 12d, unlike the other active derivatives, was able to significantly bind dimers of alpha- and beta-tubulin, probably causing a molecular distortion resulting in the disassembly of microtubules. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis and docking studies of thiophene scaffolds in COX-2
  作者：Parvesh Singh、Parul Sharma、Krishna Bisetty、Mohinder Pal Mahajan

  DOI：10.3998/ark.5550190.0012.a05

  日期：——

  A series of new thiophene compounds 6a-6l was synthesized from the reactions of in situ generated cross-conjugated enaminothiones 2 and α-bromoketones/ethyl bromoacetate. Moreover, the synthesis of 1,3-thiazine 12 and functionalized thiopyran 18 heterocycles from the cycloaddition reactions of N,N’-bis[(dimethylamino)methylene]thiourea 9, is also described. Additionally, the binding conformations of

  由原位产生的交叉共轭烯氨基硫酮2和α-溴酮/溴乙酸乙酯反应合成了一系列新的噻吩化合物6a-6l。此外，还描述了从 N,N'-双 [(二甲氨基) 亚甲基] 硫脲 9 的环加成反应合成 1,3-噻嗪 12 和官能化的噻喃 18 杂环。此外，这些化合物 6a-6l 和一些抗炎药 (NSAID) 的结合构象是通过它们在 Cyclooxygenase-2 (COX-2) 酶的活性位点的对接来确定的。