3-(1,3-Benzodioxol-5-yl)-1-(2-methoxyphenyl)prop-2-en-1-one | 169804-69-7

• 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: 3-(1,3-Benzodioxol-5-yl)-1-(2-methoxyphenyl)prop-2-en-1-one
• CAS: 169804-69-7
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: HRTALROPUCNKSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1,3-Benzodioxol-5-yl)-1-(2-methoxyphenyl)prop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel pyrazoline-containing derivatives as potential tubulin assembling inhibitors

  摘要：

  A series of novel pyrazoline-containing derivatives (15-47) has been designed, synthesized and evaluated for their biological activities. Among them, compound 18 displayed the most potent antiproliferative activity against A549, MCF-7 and HepG-2 cells line (IC50 = 0.07 mu M, 0.05 mu M, 0.03 mu M, respectively) and the tubulin polymerization inhibitory activity (IC50 = 1.88 mu M), being comparable to CA-4. Furthermore, we also tested that compound 18 was a potent inducer of apoptosis in HepG-2 cells and it had cellular effects typical for microtubule interacting agents, causing accumulation of cells in the G2/M phase of the cell cycle. These studies, along with molecular docking, provided a new molecular scaffold for the further development of antitumor agents that target tubulin. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.058
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-(1,3-Benzodioxol-5-yl)-1-(2-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel pyrazoline-containing derivatives as potential tubulin assembling inhibitors

  摘要：

  A series of novel pyrazoline-containing derivatives (15-47) has been designed, synthesized and evaluated for their biological activities. Among them, compound 18 displayed the most potent antiproliferative activity against A549, MCF-7 and HepG-2 cells line (IC50 = 0.07 mu M, 0.05 mu M, 0.03 mu M, respectively) and the tubulin polymerization inhibitory activity (IC50 = 1.88 mu M), being comparable to CA-4. Furthermore, we also tested that compound 18 was a potent inducer of apoptosis in HepG-2 cells and it had cellular effects typical for microtubule interacting agents, causing accumulation of cells in the G2/M phase of the cell cycle. These studies, along with molecular docking, provided a new molecular scaffold for the further development of antitumor agents that target tubulin. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.058

文献信息

• Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors
  作者：Mehtap TUĞRAK、Halise İnci GÜL、Hiroshi SAKAGAMİ、Rüya KAYA、İlhami GÜLÇİN

  DOI：10.3906/kim-2009-37

  日期：——

  Cancer is a disease characterized by the continuous growth of cells without adherence to the rules that healthy normal cells obey. Carbonic anhydrase I and II (CA I and CA II) inhibitors are used for the treatment of some diseases. The available drugs in the market have limitations or side effects, which bring about the need to develop new drug candidate compound(s) to overcome the problems at issue

  癌症是一种疾病，其特征是细胞不断生长，但不遵守健康的正常细胞所遵循的规则。碳酸酐酶 I 和 II（CA I 和 CA II）抑制剂用于治疗某些疾病。市场上现有的药物存在局限性或副作用，这就需要开发新的候选药物化合物来克服这些问题。在本研究中，新型吡唑-磺酰胺杂化化合物 4-[5-(1,3-benzodioxol-5-yl)-3-aryl-4,5-dihydro-1H-pyrazol-1-yl] 苯磺酰胺 (4a - 4j) 旨在发现新的候选药物化合物。合成了化合物4a-4j，并使用光谱技术确认了它们的化学结构。测试的假设是甲氧基和多甲氧基的引入是否会导致化合物的效能选择性表达 (PSE) 值增加，这反映了化合物的细胞毒性和选择性。化合物对肿瘤细胞系的细胞毒性在 6.7 - 400 µM 的范围内。化合物 4i (PSE2 = 461.5) 和 4g (PSE1 = 193.2) 在细胞毒性试验中具有最高的
• QSAR, in silico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neuraminidase
  作者：Marzieh Yaeghoobi、Neni Frimayanti、Chin Fei Chee、Kusaira K. Ikram、Belal O. Najjar、Sharifuddin M. Zain、Zanariah Abdullah、Habibah A. Wahab、Noorsaadah Abd. Rahman

  DOI：10.1007/s00044-016-1636-5

  日期：2016.10

  H1N1 neuraminidase activity by using MUNANA assay [2′-(4-methylumbelliferyl)-α-d-N-acetylneuraminic acid] assay with DANA (2,3-didehydro-2-deoxy-N-acetylneuraminic acid) was used as standard. 2D and 3D-quantitative structure−activity relationship models have been successfully developed with a good correlative and predictive ability for quantitative structure−activity relationships of these chalcone

  三十3查耳酮通过使用MUNANA测定合成和对病毒H1N1神经氨酸酶活性测试[2' - （4-甲基伞形基）-α- d - Ñ -acetylneuraminic酸]测定与DANA（2,3-二脱氢-2-脱氧Ñ-乙酰神经氨酸）作为标准。已经成功开发了2D和3D定量结构-活性关系模型，这些模型对这些查尔酮衍生物的定量结构-活性关系具有良好的相关性和预测能力。二维定量结构-活性关系模型的结果表明，静电参数增强了查耳酮的生物活性，而空间取代基减弱了其作为H1N1神经氨酸酶抑制剂的能力。3D定量结构-活性关系模型显示了查尔酮衍生物中羟基位置的重要性，该位置会影响疏水性，氢键供体和增强生物活性的芳环特征。最后，对接研究表明，查尔肯斯MC8和具有低C docker相互作用能和更多氢键键合的MC16对病毒H1N1神经氨酸酶具有更好的抑制活性。
• The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells
  作者：Ketan C. Ruparelia、Sabahat Lodhi、Dyan N. Ankrett、Nicola E. Wilsher、Randolph R.J. Arroo、Gerard A. Potter、Kenneth J.M. Beresford

  DOI：10.1016/j.bmcl.2019.03.030

  日期：2019.6

  As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP) 1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6-60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.
• Design, synthesis and biological evaluation of novel pyrazoline-containing derivatives as potential tubulin assembling inhibitors
  作者：Ya-Juan Qin、Yu-jing Li、Ai-Qin Jiang、Meng-Ru Yang、Qi-Zhang Zhu、Hong Dong、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2015.02.058

  日期：2015.4

  A series of novel pyrazoline-containing derivatives (15-47) has been designed, synthesized and evaluated for their biological activities. Among them, compound 18 displayed the most potent antiproliferative activity against A549, MCF-7 and HepG-2 cells line (IC50 = 0.07 mu M, 0.05 mu M, 0.03 mu M, respectively) and the tubulin polymerization inhibitory activity (IC50 = 1.88 mu M), being comparable to CA-4. Furthermore, we also tested that compound 18 was a potent inducer of apoptosis in HepG-2 cells and it had cellular effects typical for microtubule interacting agents, causing accumulation of cells in the G2/M phase of the cell cycle. These studies, along with molecular docking, provided a new molecular scaffold for the further development of antitumor agents that target tubulin. (C) 2015 Elsevier Masson SAS. All rights reserved.