(E)-1-(4-morpholinophenyl)-3-phenylprop-2-en-1-one | 1092492-40-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(4-morpholinophenyl)-3-phenylprop-2-en-1-one
• 英文别名: (E)-1-(4-morpholin-4-ylphenyl)-3-phenylprop-2-en-1-one
• CAS: 1092492-40-4
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: LDOJSLUMVHEGBG-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (E)-1-(4-morpholinophenyl)-3-phenylprop-2-en-1-one 在 ammonium acetate 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 正丁醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  BIOREDUCIBLE N-OXIDE-BASED PROBES FOR IMAGING OF HYPOXIA

  摘要：

  缺氧发生在氧供应有限时，会影响生理功能，是许多疾病的病理标志，包括癌症和缺血。因此，检测缺氧可以指导治疗规划，并作为患者预后的预测因子。目前的方法存在侵入性、分辨率低和特异性差的问题。为了解决这些限制，披露了各种缺氧响应探针（HyPs）用于光声成像。这种新兴的模式将安全的非电离辐射光转换为超声波，从而实现在深层组织中获取高分辨率的3D图像。HyPs具有一种N-氧化物触发器，可以被血红蛋白蛋白如CYP450酶等在没有氧气的情况下还原。还原HyPs会产生一种光谱明显不同的产物，便于通过光声成像进行识别。HyPs在体外、活细胞中以及多种疾病模型中显示出对缺氧激活的选择性。HyPs还与近红外荧光成像兼容，确立了其作为多模态成像试剂的多功能性。

  公开号：

  US20200062784A1
• 作为产物：
  描述：

  4-氟苯乙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 (E)-1-(4-morpholinophenyl)-3-phenylprop-2-en-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

• Synthesis and biological evaluation of novel chalcones bearing morpholine moiety as antiproliferative agents
  作者：BEDRİYE SEDA KURŞUN AKTAR、EMİNE ELÇİN ORUÇ-EMRE、İBRAHİM DEMİRTAŞ、AYŞE ŞAHİN YAĞLIOĞLU、AYŞEGÜL KARAKÜÇÜK İYİDOĞAN、ÇAĞLAR GÜLER、ŞEVKİ ADEM

  DOI：10.3906/kim-1705-28

  日期：——

  In this research, a new series of ($E)$-3-(4-substitutedphenyl)-1-(4'-morpholinophenyl)prop-2-en-1-one derivatives 1-7 was synthesized, aiming to develop effective antiproliferative agents. The antiproliferative activities of compounds 1-7 were examined against HeLa and C6 cell lines at eight different concentrations using the BrdU ELISA assay. The activity results were compared with reference anticancer drug 5-fluorouracil (5-FU). Compound 1 had almost the same antiproliferative activity as 5-FU. Compounds 1-7 were found to have greater effects against the C6 cell line than the HeLa cell line. These compounds were also tested in order to determine their effects on enzyme activities. Compounds 2 and 3 exhibited strong activator characteristics against pyruvate kinase isoenzyme M2 (PKM2) with AC$_50}$ values of 2.2 and 14.28 $\mu $M\textbf. Compounds 2, 3, and 7acted as inhibitors with IC$_50}$ values in the range of 84.08-165.38 $\mu $M for carbonic anhydrase isoenzyme I (hCA I), and compounds 3 and 4 demonstrated inhibitory effects against carbonic anhydrase isoenzyme II (hCA II) with IC$_50}$ values of 108.11 and 112.52 $\mu $M, respectively. hCA II was activated by derivatives 1, 2, 6, and 7} with AC$_50}$ values in the range of 85.53-146.59 $\mu $M.

  本研究合成了一系列新的($E)$-3-(4-取代苯基)-1-(4'-吗啉苯基)丙-2-烯-1-酮衍生物 1-7，旨在开发有效的抗增殖剂。利用 BrdU 酶联免疫吸附法检测了八种不同浓度的化合物 1-7 对 HeLa 和 C6 细胞株的抗增殖活性。活性结果与参考抗癌药物 5-氟尿嘧啶（5-FU）进行了比较。化合物 1 的抗增殖活性与 5-FU 几乎相同。化合物 1-7 对 C6 细胞系的作用大于 HeLa 细胞系。还对这些化合物进行了测试，以确定它们对酶活性的影响。化合物 2 和 3 对丙酮酸激酶同工酶 M2（PKM2）表现出很强的激活特性，其 AC$_50}$ 值分别为 2.2 和 14.28 $\mu $M\textbf。化合物 2、3 和 7 对碳酸酐酶同工酶 I（hCA I）具有抑制作用，IC$_50}$ 值范围为 84.08-165.38 $\mu $M；化合物 3 和 4 对碳酸酐酶同工酶 II（hCA II）具有抑制作用，IC$_50}$ 值范围为 108.hCA II 被衍生物 1、2、6 和 7 激活，其 AC$_50}$ 值范围为 85.53-146.59 $\mu $M。
• SYNTHESIS AND SPECTRAL ANALYSIS OF AN ARRAY OF NOVEL 4-(4-MORPHOLINOPHENYL)-6-ARYL-PYRIMIDIN-2-AMINES
  作者：J THANUSU、V KANAGARAJAN、M GOPALAKRISHNAN

  DOI：10.4067/s0717-97072010000400022

  日期：——

  nitrate; Synthesis. e-mail: [e-mail] INTRODUCTION Pyrimidines are the basic nucleus in nucleic acids and have been associ-ated with a number of biological activities. Some notable biological activity of pyrimidine derivatives include adenosine receptor antagonists [1], kinase inhibitors [2], analgesic [3], anti-inflammatory [3], inhibitors of cyclin-De-pendent kinases 1 and 2 [4], calcium channel

  摘要从各自的（E）-1-4-吗啉代苯基）-3-芳基-prop-2合成了一系列新合成的新型4-（4-吗啉代苯基）-6-芳基嘧啶-2-胺（20-28）。 -en-1-ones（11-19），通过氢氧化锂催化回流乙醇中的硝酸胍处理，并通过熔点，元素分析，MS，FT-IR，一维NMR（1 H和13 C）表征光谱数据。关键字：1-（4-吗啉代苯基）乙酮；（E）-1-4-吗啉代苯基）-3-芳基-丙-2-烯-1-酮; 4-（4-吗啉代苯基）-6-芳基嘧啶-2-胺; 硝酸胍; 合成。电子邮件：[e-mail]简介嘧啶是核酸中的基本核，并已与许多生物学活性相关联。嘧啶衍生物的一些重要生物活性包括腺苷受体拮抗剂[1]，激酶抑制剂[2]，止痛药[3]，抗炎药[3]，细胞周期蛋白依赖性激酶1和2抑制剂[4]，钙通道拮抗剂[5]，抗组胺药[6]，抗结核药[7] 。取代的氨基嘧啶核在市售药物中很
• Merging Photocatalytic Doubly‐Decarboxylative C_sp²−C_sp² Cross‐Coupling for Stereo‐Selective (<i>E</i>)‐<i>α</i>,<i>β</i>‐Unsaturated Ketones Synthesis
  作者：Subal Mondal、Siba P. Midya、Soumya Mondal、Suman Das、Pradyut Ghosh

  DOI：10.1002/chem.202303337

  日期：2024.1.26

  cross-coupling reaction. Present catalytic system efficiently cross-coupled α, β-unsaturated acids and α-keto acids to a variety of α, β-unsaturated ketones with excellent E-selectivity and functional group tolerance. In this merging catalysis, photocatalyst implicated through reductive quenching cycle whereas cross coupling proceeded over one electron oxidative pallado-cycle in a tandem pathway.

  在此，我们首次报道了光催化双脱羧C sp 2 -C sp 2交叉偶联反应。该催化体系能够将α , β-不饱和酸和α-酮酸与多种α , β-不饱和酮有效交叉偶联，具有优异的E-选择性和官能团耐受性。在这种合并催化中，光催化剂涉及还原猝灭循环，而交叉耦合则在串联途径中的一个电子氧化帕拉多循环上进行。
• Morpholine-based chalcones as dual-acting monoamine oxidase-B and acetylcholinesterase inhibitors: synthesis and biochemical investigations
  作者：Rani Sasidharan、Bo Hyun Eom、Jeong Hyun Heo、Jong Eun Park、Mohamed A. Abdelgawad、Arafa Musa、Nicola Gambacorta、Orazio Nicolotti、Sreedharannair Leelabaiamma Manju、Bijo Mathew、Hoon Kim

  DOI：10.1080/14756366.2020.1842390

  日期：2021.1.1

  Nine compounds (MO1-MO9) containing the morpholine moiety were assessed for their inhibitory activities against monoamine oxidases (MAOs) and acetylcholinesterase (AChE). Most of the compounds potently inhibited MAO-B; MO1 most potently inhibited with an IC₅₀ value of 0.030 µM, followed by MO7 (0.25 µM). MO5 most potently inhibited AChE (IC₅₀ = 6.1 µM), followed by MO9 (IC₅₀ = 12.01 µM) and MO7 most potently inhibited MAO-A (IC₅₀ = 7.1 µM). MO1 was a reversible mixed-type inhibitor of MAO-B (K_i = 0.018 µM); MO5 reversibly competitively inhibited AChE (K_i = 2.52 µM); and MO9 reversibly noncompetitively inhibited AChE (K_i = 7.04 µM). MO1, MO5 and MO9 crossed the blood-brain barrier, and were non-toxic to normal VERO cells. These results show that MO1 is a selective inhibitor of MAO-B and that MO5 is a dual-acting inhibitor of AChE and MAO-B, and that both should be considered candidates for the treatment of Alzheimer's disease.
• Design, synthesis and anticancer activity of new 3-cyano-2 (1H) -pyridone and 3-cyanopyridine-2-(1H)-thione Derivatives
  作者：E. A Abdel、M. A Salem、M. H Helal、M. S. A El-Gaby

  DOI：10.13005/ojc/310230

  日期：2015.6.20

  The main objective of the present research study is to synthesize some novel chalcone, cyanoacetohydrazone, enaminone, 3-cyano-2(1H)-pyridone and 3-cyanopyridine-2-(1H)-thione derivatives and evaluate them for their anticancer effect. The novel chalcones 2a-c were achieved by Claisen-Schmidt condensation of appropriate benzaldehydes with ethanone derivative 1. Treatment of cyanoacetic acid hydrazide with ethanone derivative 1 yielded the correspondinghydrazone derivative 3. Condensation of ethanone derivative 1 with DMF-DMA afforded (E)-3-(dimethylamino)-1- (4- morpholinophenyl)prop-2-en-1-one 4. Heterocyclization of chalcones 2a-c with cyanothioacetamide yielded 2-thioxo-1,2-dihydropyridine-3-carbonitriles 7a-c. In a similar manner, cyclocondensation of chalcones 2a,b with cyanoacetamide afforded the corresponding 2-oxo-1,2-dihydropyridine-3-carbonitriles 8a,b.  The Reaction of compound 2a with ethyl cyanoacetate furnished 2-oxo-1,2-dihydropyridine-3-carboxylate 12. The 2-oxo-4-phenyl-1,2-dihydro-pyridine-3,5-dicarbonitriles 14a,b were obtained by  cyclization of cyano-acetohydrazone 3 with cinnamonitriles. The structures of the synthesized compounds were confirmed by elemental analysis, mass spectrometry, IR and 1H-NMR spectroscopy. The anticancer  activity of the newly synthesized compounds was screened in vitro against Human lung carcinoma (A 549) cell line indicating that compounds 7b  and  8a possess the most potent inhibitory effect against the human lung carcinoma cell line (A549).

  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。