(2E)-3-(dimethylamino)-1-(4-morpholinophenyl)-2-propen-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2E)-3-(dimethylamino)-1-(4-morpholinophenyl)-2-propen-1-one
• 英文别名: (E)-3-(dimethylamino)-1-(4-morpholinophenyl)prop-2-en-1-one；3-(dimethylamino)-1-(4-morpholinophenyl)prop-2-en-1-one；3-dimethylamino-4'-morpholinoacrylophenone；(2E)-3-(dimethylamino)-1-[4-(morpholin-4-yl)phenyl]prop-2-en-1-one；(E)-3-(dimethylamino)-1-(4-morpholin-4-ylphenyl)prop-2-en-1-one
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: NRBSCEJIZYRBPD-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-3-(dimethylamino)-1-(4-morpholinophenyl)-2-propen-1-one 生成 4-[4-(4-Morpholinyl)phenyl]imidazo[1,5-a]pyrimidine-8-carboxamide
  参考文献：
  名称：

  TSENG, SHIN S.;DUSZA, JOHN P.;EPSTEIN, JOSEPH W.

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氟苯乙酮 在 potassium carbonate 作用下， 以 二甲基亚砜 、 间二甲苯 为溶剂， 反应 4.0h， 生成 (2E)-3-(dimethylamino)-1-(4-morpholinophenyl)-2-propen-1-one
  参考文献：
  名称：

  Design, synthesis and anticancer activity of new 3-cyano-2 (1H) -pyridone and 3-cyanopyridine-2-(1H)-thione Derivatives

  摘要：

  本研究的主要目的是合成一些新颖的查尔酮、氰基乙酰腙、烯胺酮、3-氰基-2(1H)-吡啶酮和3-氰基吡啶-2-(1H)-噻唉衍生物，并评估它们的抗癌效果。通过Claisen-Schmidt缩合反应，将适当的苯甲醛与乙酮衍生物1反应，合成了新型的查尔酮2a-c。氰基乙酸酰肼与乙酮衍生物1反应得到了相应的酰肼衍生物3。乙酮衍生物1与DMF-DMA缩合反应得到了(E)-3-(二甲基氨基)-1-(4-吗啉基苯基)丙-2-烯-1-酮4。查尔酮2a-c与氰硫乙酰胺的杂环化反应得到了2-硫代-1,2-二氢吡啶-3-腈7a-c。类似地，查尔酮2a,b与氰乙酰胺的环缩合反应得到了相应的2-氧代-1,2-二氢吡啶-3-腈8a,b。化合物2a与氰乙酸乙酯反应得到了2-氧代-1,2-二氢吡啶-3-羧酸酯12。通过氰乙酰肼3与肉桂腈的环化反应得到了2-氧代-4-苯基-1,2-二氢吡啶-3,5-二腈14a,b。通过元素分析、质谱、红外光谱和1H-NMR光谱，确认了合成化合物的结构。新合成化合物的抗癌活性在体外对人肺腺癌(A549)细胞系进行了筛选，结果显示化合物7b和8a对人类肺腺癌细胞系(A549)具有最强的抑制效果。

  DOI：

  10.13005/ojc/310230

文献信息

• Enaminone-Derived Pyrazoles with Antimicrobial Activity
  作者：Mashooq Ahmad Bhat、Mohamed A. Al-Omar、Ahmed M. Naglah、Abdul Arif Khan

  DOI：10.1155/2019/2467970

  日期：2019.11.7

  A series of pyrazoles derived from the substituted enaminones were synthesized and were evaluated for antimicrobial activity. All the compounds were characterized by the spectral data and elemental analysis. The synthesized compounds were initially screened for their antimicrobial activity against ATCC 6538, NCTC 10400, NCTC 10418, and ATCC 27853. During initial screening, compounds (P1, P6, and P11) presented significant antimicrobial activity through disc diffusion assay. These compounds were further evaluated for antimicrobial activity at different time points against Gram-positive and Gram-negative bacteria and presented significant activity for 6 hours. The activity was found to be greater against Gram-positive bacteria. In contrast at 24 hours, the activity was found only against Gram-positive bacteria except compound (P11), showing activity against both types of bacteria. Compound (P11) was found to have highest activity against both Gram-positive and Gram-negative bacteria.

  一系列由取代烯酮酮合成的吡唑类化合物被合成，并评估其抗微生物活性。所有化合物均通过光谱数据和元素分析进行表征。合成的化合物最初针对ATCC 6538、NCTC 10400、NCTC 10418和ATCC 27853进行了抗微生物活性筛选。在初步筛选中，化合物（P1、P6和P11）通过圆盘扩散法展现出显著的抗微生物活性。这些化合物随后在不同时间点针对革兰氏阳性和阴性细菌进行了抗微生物活性评估，并在6小时内展现出显著活性。活性在革兰氏阳性细菌中表现更强。相反，在24小时内，活性仅在革兰氏阳性细菌中发现，除了化合物（P11）外，后者对两种类型的细菌均表现出活性。化合物（P11）被发现对革兰氏阳性和阴性细菌均具有最高活性。
• A One-Pot Biginelli Synthesis and Characterization of Novel Dihydropyrimidinone Derivatives Containing Piperazine/Morpholine Moiety
  作者：Mashooq Bhat、Mohamed Al-Omar、Hazem Ghabbour、Ahmed Naglah

  DOI：10.3390/molecules23071559

  日期：——

  any solvent. The three dimensional structure of enaminone (IIb) containing morpholine moiety was confirmed by single crystal X-ray crystallography. Finally, the dihydropyrimidinone derivatives (1⁻20) were obtained by reacting enaminones (IIa⁻b) with urea and different substituted benzaldehydes in the presence of glacial acetic acid. Dihydropyrimidinone derivatives containing piperazine/morpholine moiety

  烯胺酮通过回流1- [4-（哌嗪/吗啉-），合成4-甲基-1- [4-（哌嗪/吗啉-1-基）苯基]戊-2-烯-1-酮（IIa⁻b）。 1-yl）苯基]乙-1-酮（Ia⁻b）与二甲基甲酰胺二甲基乙缩醛（DMF⁻DMA），无需任何溶剂。通过单晶X射线晶体学确认了含有吗啉部分的烯胺酮（IIb）的三维结构。最后，在冰醋酸存在下，烯胺（IIa⁻b）与尿素和不同的取代苯甲醛反应，制得二氢嘧啶酮衍生物（1⁻20）。通过简单有效的方法，以高收率合成了含有哌嗪/吗啉部分的二氢嘧啶酮衍生物。
• Substituted-6H,8H-pyrimido-[1,2,3-cd]purine-8,10-(9H)-diones and
  申请人：American Cyanamid Company

  公开号：US04904658A1

  公开（公告）日：1990-02-27

  Substituted-6H,8H-pyrimido[1,2,3-cd]purine-8,10(9H)-diones and substituted-6H,10H-pyrimido[1,2-cd]purin-10-ones which are useful as cognition enhancing agents, anxiolytic agents and/or antihypertensive agents in the treatment of cognitive and relative neutral behavioral problems, anxiety and hypertension in mammals.

  Substituted-6H,8H-嘧啶并[1,2,3-cd]嘌呤-8,10(9H)-二酮和替代的6H,10H-嘧啶并[1,2-cd]嘌呤-10-酮，可用作改善认知、抗焦虑和/或降压剂，用于治疗哺乳动物的认知和相关神经行为问题、焦虑和高血压。
• 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.
• TSENG, SHIN S.;EPSTEIN, JOSEPH W.;LEVIN, L.
  作者：TSENG, SHIN S.、EPSTEIN, JOSEPH W.、LEVIN, L.

  DOI：——

  日期：——