[2-(4-Ethylphenyl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)methanone | 1429621-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(4-Ethylphenyl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)methanone
• 英文别名: [2-(4-ethylphenyl)-1H-imidazol-5-yl]-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1429621-66-8
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: UFZXVQZPLIVXRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-乙基苯甲醛 在 ammonium hydroxide 、 四丁基氟化铵 、 水 、 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 、 正戊烷 为溶剂， 生成 [2-(4-Ethylphenyl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Discovery of 4-Aryl-2-benzoyl-imidazoles as Tubulin Polymerization Inhibitor with Potent Antiproliferative Properties

  摘要：

  A series of 4-aryl-2-benzoyl-imidazoles were designed and synthesized based on our previously reported 2-aryl-4-benzoyl-imidazole (ABI) derivatives. The new structures reversed the aryl group and the benzoyl group of previous ABI structures and were named as reverse ABI (RABI) analogues. RABIs were evaluated for biological activity against eight cancer cell lines including multidrug-resistant cancer cell lines. In vitro assays indicated that several RABI compounds had excellent antiproliferative properties, with IC50 values in the low, nanomolar range. The average IC50 of the most active compound 12a is 14 nM. In addition, the mechanism of action of these new analogues was investigated by cell cycle analysis, tubulin polymerization assay, competitive mass spectrometry binding assay, and molecular docking studies. These studies confirmed that these new RABI analogues maintain their mechanisms of action by disrupting tubulin polymerization, similar to their parental ABI analogues.

  DOI：

  10.1021/jm4001117

文献信息

• COMPOUNDS FOR TREATMENT OF CANCER
  申请人：Miller Duane D.

  公开号：US20090326020A1

  公开（公告）日：2009-12-31

  Compounds according to formula (I) are disclosed where Q is S, N, or O; X is optional, and can be O═, S═, ═N—NH 2 , ═N—OH, or —OH; Y is optional and can be —N(H)—, O, or C 1 to C 20 hydrocarbon; and R 1 and R 2 are each independently substituted or unsubstituted single-, fused- or multiple-ring aryl or (hetero)cyclic ring systems. Methods of making these compounds, pharmaceutical compositions containing the compounds, and their use, particularly for treating or preventing cancer, are also disclosed.

  根据公式（I）披露的化合物如下：其中Q为S、N或O；X为可选，可以是O═、S═、═N—NH2、═N—OH或—OH；Y为可选，可以是—N(H)—、O或C1至C20碳氢化合物；而R1和R2分别独立地为取代或未取代的单环、融合环或多环芳基或（杂）环烷基环系统。还披露了制备这些化合物的方法、含有这些化合物的药物组合物，以及它们的用途，特别是用于治疗或预防癌症。
• COMPOUND FOR TREATMENT OF CANCER
  申请人：University of Tennessee Research Foundation

  公开号：EP2959900A1

  公开（公告）日：2015-12-30

  A compound, wherein the compound is (2-(1H-indol-3-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone. A pharmaceutical composition comprising the compound is (2-(1H-indol-3-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone and a pharmaceutically acceptable carrier. The compound (2-(1H-indol-3-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone for use in treating prostate cancer, breast cancer, ovarian cancer, skin cancer, lung cancer, colon cancer, leukemia, renal cancer or CNS cancer, or a combination thereof.

  一种化合物，其中化合物为(2-(1H-吲哚-3-基)咪唑-4-基)(3,4,5-三甲氧基苯基)甲酮。 一种药物组合物，包含化合物 (2-(1H-吲哚-3-基)咪唑-4-基)(3,4,5-三甲氧基苯基)甲酮和药学上可接受的载体。 (2-(1H-吲哚-3-基)咪唑-4-基)(3,4,5-三甲氧基苯基)甲酮化合物用于治疗前列腺癌、乳腺癌、卵巢癌、皮肤癌、肺癌、结肠癌、白血病、肾癌或中枢神经系统癌症，或它们的组合。
• Compounds for treatment of cancer
  申请人：University of Tennessee Research Foundation

  公开号：US10301285B2

  公开（公告）日：2019-05-28

  The present invention relates to a compound of formula XXII and a compound of formula 17ya, which are defined as anywhere in the specification, to a composition comprising the same, and to a method of using thereof in the treatment of various forms of cancer.

  本发明涉及一种式 XXII 化合物和一种式 17ya 化合物（在说明书的任何地方都有定义），涉及一种包含这些化合物的组合物，还涉及一种将其用于治疗各种癌症的方法。
• US8592465B2
  申请人：——

  公开号：US8592465B2

  公开（公告）日：2013-11-26
• US9029408B2
  申请人：——

  公开号：US9029408B2

  公开（公告）日：2015-05-12