(E)-3-(4-chlorophenyl)-1-(4-morpholinophenyl)prop-2-en-1-one | 1050196-71-8

• 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)-3-(4-chlorophenyl)-1-(4-morpholinophenyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-chlorophenyl)-1-(4-morpholin-4-ylphenyl)prop-2-en-1-one；3-(4-Chlorophenyl)-1-[4-(morpholin-4-yl)phenyl]prop-2-en-1-one
• CAS: 1050196-71-8
• 化学式: C₁₉H₁₈ClNO₂
• 分子量: 327.81
• InChiKey: LCUHOSRXQHYXCP-XCVCLJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 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)-3-(4-chlorophenyl)-1-(4-morpholinophenyl)prop-2-en-1-one 、 硝酸胍 在 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以78%的产率得到4-(4-chlorophenyl)-6-(4-morpholin-4-ylphenyl)pyrimidin-2-amine
  参考文献：
  名称：

  新型4-（4-甲氧亚苯基）-6-芳基-嘧啶-2-胺的阵列的合成及光谱分析

  摘要：

  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

  DOI：

  10.4067/s0717-97072010000400022
• 作为产物：
  描述：

  4-(4-吗啉基)苯乙酮 、 4-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以90%的产率得到(E)-3-(4-chlorophenyl)-1-(4-morpholinophenyl)prop-2-en-1-one
  参考文献：
  名称：

  新型4-（4-甲氧亚苯基）-6-芳基-嘧啶-2-胺的阵列的合成及光谱分析

  摘要：

  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

  DOI：

  10.4067/s0717-97072010000400022

文献信息

• Synthesis of novel substituted 1,3-diaryl propenone derivatives and their antimalarial activity in vitro
  作者：Nidhi Mishra、Preeti Arora、Brajesh Kumar、Lokesh C. Mishra、Amit Bhattacharya、Satish K. Awasthi、Virendra K. Bhasin

  DOI：10.1016/j.ejmech.2007.09.014

  日期：2008.7

  The synthesis of novel 1,3-diaryl propenone derivatives and their antimalarial activity in vitro against asexual blood stages of human malaria parasite, Plasmodium falciparum, are described. Chalcone derivatives were prepared via Claisen-Schmidt condensation of substituted aldehydes with substituted methyl ketones. Antiplasmodial IC(50) (half maximal inhibitory concentration) activity of these compounds

  描述了新型1，3-二芳基丙烯酮衍生物的合成及其体外抗人疟疾寄生虫恶性疟原虫无性血液阶段的抗疟活性。通过取代的醛与取代的甲基酮的克莱森-施密特缩合制备查耳酮衍生物。这些化合物的抗血浆IC（50）（最大抑制浓度的一半）活性介于1.5和12.3 microg / ml之间。发现氯系列1,2,4-三唑取代的查尔酮在体外抑制恶性疟原虫的生长最有效，而吡咯和苯并三唑取代的查耳酮则显示出相对较低的抑制活性。这是有关苯乙酮环上的查尔酮类与吡咯类抗疟原虫活性的首次报道。
• Synthesis and bio-evaluation of alkylaminoaryl phenyl cyclopropyl methanones as antitubercular and antimalarial agents
  作者：Arya Ajay、Vandana Singh、Shubhra Singh、Swaroop Pandey、Sarika Gunjan、Divya Dubey、Sudhir Kumar Sinha、Bhupendra N. Singh、Vinita Chaturvedi、Renu Tripathi、Ravishankar Ramchandran、Rama P. Tripathi

  DOI：10.1016/j.bmc.2010.09.071

  日期：2010.12

  A series of 4-alkylaminoaryl phenyl cyclopropyl methanones (6a-6u and 8a-8c) were synthesized from 4-fluorochalcones (3a and 3b) by cyclopropanation of double bond followed by nucleophilic substitution of F with different amines. The compounds were screened for their antitubercular and antimalarial activities against Mycobacterium tuberculosis H37Rv and Plasmodium falciparum 3D7 strains in vitro respectively. Several compounds (6a, 6d-6h, 6p, 6q and 8a-8c) exhibited good in vitro antitubercular activities with MIC values 3.12-12.5 mu g/mL and preferentially inhibited the growth of P. falciparum in vitro (4a, 4c, 6a-6d, 6f, 6s, 8a and 8c) with IC50 as low as 0.080 and 0.035 mu g/mL and SI values 4975 and 6948, respectively. Molecular docking studies and in vitro evaluation against FAS-II enzymes using reporter gene assays were carried out to elucidate the mode of action of these molecules. Two compounds 4a and 6g showed significant inhibition at 25 mu M concentration of the compound. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.