(E)-1-(3,4,5-trimethoxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one | 1309371-25-2

• 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-(3,4,5-trimethoxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one
• 英文别名: (E)-3-(2-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1309371-25-2
• 化学式: C₁₈H₁₇NO₆
• 分子量: 343.336
• InChiKey: JLLXCSCZPKIRIF-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(3,4,5-trimethoxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one 在 对甲基苯磺酰甲基异腈 、 copper diacetate 、 sodium hydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 22.0h， 生成 (1-(4-fluorophenyl)-4-(2-nitrophenyl)-1H-pyrrol-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Structure-activity relationship studies and in vitro and in vivo anticancer activity of novel 3-aroyl-1,4-diarylpyrroles against solid tumors and hematological malignancies

  摘要：

  Novel 3-aroyl-1,4-diarylpyrrole derivatives were synthesized to explore structure-activity relationships at the phenyls at positions 1 and 4 of the pyrrole. The presence of amino phenyl rings at positions 1 and 4 of the pyrrole ring were found to be a crucial requirement for potent antitumor activity. Several compounds strongly inhibited tubulin assembly through binding to the colchicine site. Compounds 42, 44, 48, 62 and 69 showed antitumor activity with low nanomolar 1050 values in several cancer cell lines. Compound 48 was generally more effective as an inhibitor of glioblastoma, colorectal and urinary bladder cancer cell lines; 69 consistently inhibited CML cell lines and demonstrated superiority in nilotinib and imatinib resistant LAMA84-R and KBM5-T3151 cells. In animal models, compound 48 exhibited significant inhibition of the growth of T24 bladder carcinoma and ES-2 ovarian clear cell carcinoma tumors. Compounds 48 and 69 represent robust lead compounds for the design of new broadspectrum anticancer agents active in different types of solid and hematological tumors. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111828
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 邻硝基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以42%的产率得到(E)-1-(3,4,5-trimethoxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  新型吡唑并[4,3-c][2,1]苯并噻嗪4,4-二氧化物衍生物的合成、抗炎和细胞毒活性

  摘要：

  13 种新型吡唑并[4,3 - c ][2,1]苯并噻嗪 4,4-二氧化物衍生物模拟吡罗昔康和塞来昔布的药效团，采用无催化剂和原子经济的方法方便地合成，其中非常规的氧化还原- 2-硝基查尔酮与元素硫的中性反应直接获得 2,1-苯并噻嗪 2,2-二氧化物核是关键步骤。八新吡唑啉[4,3- c][2,1]苯并噻嗪衍生物比阳性对照显着抑制 NO 的产生。除此之外，大多数化合物表现出较弱的细胞毒活性，表明与这些新化合物的抗增殖活性相关的有效和选择性抗炎活性。因此，将上述两种药物的药效团结合到一个分子中对于确定新化合物更好的抗炎活性起着重要作用。

  DOI：

  10.1002/jhet.4521

文献信息

• [EN] NUCLEAR RECEPTOR MODULATORS AND THEIR USE FOR THE TREATMENT AND PREVENTION OF CANCER<br/>[FR] MODULATEURS DE RÉCEPTEURS NUCLÉAIRES ET LEUR UTILISATION POUR LE TRAITEMENT ET LA PRÉVENTION D'UN CANCER
  申请人：US HEALTH

  公开号：WO2012174436A1

  公开（公告）日：2012-12-20

  Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R1 to R5 and X1 to X5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.

  本文披露了一些化合物，它们是核受体调节剂，可以作为雄激素受体的拮抗剂，例如，公式I的化合物：其中R1至R5和X1至X5如本文所述，以及其药用盐、溶剂化合物和立体异构体。还披露了包括这些化合物的药物组合物，以及使用方法和治疗癌症，包括前列腺癌、其他核受体介导的癌症和其他疾病的方法。
• NUCLEAR RECEPTOR MODULATORS AND THEIR USE FOR THE TREATMENT AND PREVENTION OF CANCER
  申请人：Neckers Jane B.

  公开号：US20140171503A1

  公开（公告）日：2014-06-19

  Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R 1 to R 5 and X 1 to X 5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.