(E)-1-(4-aminophenyl)-3-(4-bromophenyl)prop-2-en-1-one | 948840-96-8

• 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)-1-(4-aminophenyl)-3-(4-bromophenyl)prop-2-en-1-one
• 英文别名: (2E)-1-(4-aminophenyl)-3-(4-bromophenyl)prop-2-en-1-one
• CAS: 948840-96-8
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: VQJUBRITHVAKHO-XCVCLJGOSA-N

物化性质

• 沸点：
  473.4±45.0 °C(Predicted)
• 密度：
  1.450±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-aminophenyl)-3-(4-bromophenyl)prop-2-en-1-one 在 sodium phosphate dodecahydrate 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 (S,E)-2-((4-(3-(4-bromophenyl)acryloyl)phenyl)amino)-2-oxoethyl (2-oxotetrahydrofuran-3-yl)carbamodithioate
  参考文献：
  名称：

  Discovery of novel AHLs as potent antiproliferative agents

  摘要：

  Three series of novel AHL analogs were synthesized and evaluated for their in vitro cytotoxic activity against four human cancer cell lines. The SARs investigation indicated that AHLs with a terminal phenyl group, especially those with the chalcone scaffold had remarkably enhanced cytotoxicity than those with the hydrophobic side chains. Besides, some of these compounds were much more potent than 5-Fu and natural OdDHL. Through the detailed SARs discussions, we found that compounds 10a-k and 14 with the 4-amino chalcone scaffold showed excellent inhibition against all the tested cancer cell lines and were much more potent than 5-Fu and AHLs. Such scaffold may act as a template for further lead optimization. Compound 10i with a 3, 4, 5-trimethoxy group was the most potent one against all the tested cancer cell lines. Flow cytometry analysis indicated that analog lie induced the cellular apoptosis and cell cycle arrest of MCF-7 cells at G2/M phase in a concentration-and time-dependent manner. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.026
• 作为产物：
  描述：

  3-(4-溴苯基)-1-(4-硝基苯基)丙-2-烯-1-酮 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (E)-1-(4-aminophenyl)-3-(4-bromophenyl)prop-2-en-1-one
  参考文献：
  名称：

  4-氨基查耳酮衍生物的ADME特性、生物活性和分子对接研究：用于治疗阿尔茨海默病、青光眼和癫痫病的新类似物

  摘要：

  在本研究中，(E)-1-(4-aminophenyl)-3-(aryl) prop-2-en-1-one (4-amino-chalcones) 衍生物 (3a-o) 对乙酰胆碱酯酶的体外抑制作用(AChE) 酶和人红细胞碳酸酐酶 I 和 II 同工酶 (hCA I-II) 进行了研究。此外，比较了 4-氨基查耳酮衍生物对乙酰胆碱酯酶 (PDB ID: 1OCE)、人碳酸酐酶 I (PDB ID: 2CAB)、人碳酸酐酶 II (PDB ID: 3DC3) 等酶的生物活性。 . 得到结果后，为了将来将4-氨基查耳酮衍生物用作药物，进行了ADME/T分析。碳酸酐酶 I 和 II 同工酶（hCAI 和 II）和乙酰胆碱酯酶 (AChE) 酶的有效抑制剂，hCA I 的 Ki 值范围为 2.55 ± 0.35–11.75 ± 3.57 nM，hCA II 的 Ki 值范围为 4.31 ± 0.78–17

  DOI：

  10.1007/s40203-021-00094-x

文献信息

• Synthesis and cytotoxic activity of certain new arylazothiazole containing compounds
  作者：Salwa El-Meligie、Raafat A. El-Awady

  DOI：10.1002/jhet.5570390604

  日期：2002.11

  the chalcone analogues 4a-c. The pyridone derivatives 5a,b were synthesized by reacting the ketone 2d with different aromatic aldehydes, ethyl cyanoacetate and ammonium acetate. On the other hand, 5b was also prepared by cyclizing 4c with ethyl cyanoacetate and ammonium acetate. Furthermore, 6-chloroimidazo[2,l-b]-thiazole 7 was obtained from the acid derivative 6b by treatment with POC13. While, the

  通过将芳基重氮氯化物与2-氨基-4-（2-氯苯基）噻唑（1）偶联制备2-氨基-5-芳基偶氮-4-（2-氯苯基）噻唑（2a-e）。通过将芳基偶氮噻唑2a-c与适当的异硫氰酸酯缩合获得硫脲3a-e。2d与芳族醛的反应得到查耳酮类似物4a-c。通过使酮2d与不同的芳族醛，氰基乙酸乙酯和乙酸铵反应来合成吡啶酮衍生物5a，b。另一方面，也可以通过环化4c来制备5b用氰基乙酸乙酯和乙酸铵。此外，通过用POCl 3处理，从酸衍生物6b获得6-氯咪唑并[2，1- b ]-噻唑7。而咪唑并[2，1 - b ]-噻唑酮9a-d是通过将氯乙酰基衍生物8a-d与DMAP /嘧啶环化而产生的。测试了所制备化合物的代表性实例对两种人类肿瘤细胞系的体外抗肿瘤活性。一些化合物显示出针对脑肿瘤细胞系的活性。
• COMPOSITION FOR DIAGNOSIS OF AMYLOID-RELATED DISEASE
  申请人：Nakayama Morio

  公开号：US20100278733A1

  公开（公告）日：2010-11-04

  There is provided a composition comprising a compound represented by general formula (I), wherein R l represents a 5-iodothiophen-2-yl group or the like, and R 2 represents a 4-dimethylaminophenyl group or the like. This composition is useful for diagnosis of an amyloid-related disease such as Alzheimer's disease because the compound has high binding specificity to amyloid β protein, high permeability through the blood-brain barrier, and a property of being rapidly eliminated from sites other than senile plaques in the brain.

  提供了一种化合物组合物，其由一般式(I)所代表的化合物组成，其中R1代表5-碘噻吩-2-基基团或类似物，R2代表4-二甲氨基苯基基团或类似物。该组合物对于诊断与淀粉样蛋白相关的疾病，如阿尔茨海默病，具有高结合特异性，高透过血脑屏障的渗透性，以及在大脑老年斑以外的部位迅速被排除的特性。
• COMPOSITION FOR DIAGNOSING AMYLOID-RELATED DISEASE
  申请人：Nagasaki University

  公开号：EP2030635A1

  公开（公告）日：2009-03-04

  There is provided a composition comprising a compound represented by general formula (I), wherein R1 represents a 5-iodothiophen-2-yl group or the like, and R2 represents a 4-dimethylaminophenyl group or the like. This composition is useful for diagnosis of an amyloid-related disease such as Alzheimer's disease because the compound has high binding specificity to amyloid β protein, high permeability through the blood-brain barrier, and a property of being rapidly eliminated from sites other than senile plaques in the brain.

  提供了一种化合物组合物，其由一般式（I）表示的化合物组成，其中R1代表5-碘噻吩-2-基基团或类似物，R2代表4-二甲氨基苯基团或类似物。该组合物对于诊断与淀粉样蛋白相关的疾病，如阿尔茨海默病，具有高结合特异性，高透过血脑屏障的渗透性，以及在大脑老年斑以外部位迅速被排除的特性。
• Synthesis and Biological Evaluation of Amino Chalcone Derivatives as Antiproliferative Agents
  作者：Chao-Fan Lu、Sheng-Hui Wang、Xiao-Jing Pang、Ting Zhu、Hong-Li Li、Qing-Rong Li、Qian-Yu Li、Yu-Fan Gu、Zhao-Yang Mu、Min-Jie Jin、Yin-Ru Li、Yang-Yang Hu、Yan-Bing Zhang、Jian Song、Sai-Yang Zhang

  DOI：10.3390/molecules25235530

  日期：——

  Chalcone is a common scaffold found in many biologically active compounds. The chalcone scaffold was also frequently utilized to design novel anticancer agents with potent biological efficacy. Aiming to continue the research of effective chalcone derivatives to treat cancers with potent anticancer activity, fourteen amino chalcone derivatives were designed and synthesized. The antiproliferative activity

  查耳酮是在许多生物活性化合物中发现的常见支架。查耳酮支架也经常用于设计具有强大生物功效的新型抗癌剂。为了继续研究有效的查尔酮衍生物来治疗癌症，具有强大的抗癌活性，设计并合成了十四种氨基查尔酮衍生物。体外研究氨基查尔酮衍生物的抗增殖活性，5-Fu 作为对照组。一些化合物对三种人类癌细胞（MGC-803、HCT-116 和 MCF-7 细胞）显示出中等至良好的活性，化合物 13e 对 MGC-803 细胞、HCT-116 细胞和 MCF-7 显示出最好的抗增殖活性IC50 值为 1.52 μM (MGC-803)、1.83 μM (HCT-116) 和 2.54 μM (MCF-7) 的细胞，分别比阳性对照（5-Fu）更有效。进一步的机制研究进行了探索。细胞集落形成试验的结果表明化合物10e抑制MGC-803细胞的集落形成。DAPI 荧光染色和流式细胞术检测显示化合物 13e 诱导 MGC-803
• Design and synthesis of new coumarin–chalcone/NO hybrids of potential biological activity
  作者：Hany A. El-Sherief、Gamal El-Din A. Abuo-Rahma、Mai E. Shoman、Eman A. Beshr、Rehab M. Abdel-baky

  DOI：10.1007/s00044-017-2004-9

  日期：2017.12

  AbstractThis study aims at investigating a synthesis approach based on molecular hybridization strategy through grafting an nitric oxide-releasing moiety, oxime, to coumarin–chalcone hybrids. In vitro anti-proliferative activity of some of the prepared compounds showed moderate activity (growth inhibition values = 45.85, 40.86, 39.25 for compound 8a against leukemia, Central Nervous system and breast

  摘要这项研究旨在研究一种基于分子杂交策略的合成方法，该方法通过将一氧化氮释放部分肟肟嫁接到香豆素-查耳酮杂种中。某些制备的化合物的体外抗增殖活性显示中等活性（化合物8a对白血病，中枢神经系统和乳腺癌细胞的生长抑制值分别为45.85、40.86、39.25 ）。此外， 化合物8h和8f的IC 50 = 9.62和14.40，分别针对乳腺癌密歇根州癌症基金会7细胞系。抗菌筛查结果表明，一氧化氮可能在增强抗菌活性方面可能发挥作用，其中一氧化氮不是唯一因素，但应研究其他因素（如理化性质）对活性的潜在作用。 图形概要