3-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 133707-53-6

• 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: 3-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: 3‐(4‐nitrophenyl)‐1‐(3,4,5‐trimethoxyphenyl)‐2‐propen‐1‐one；4-nitro-3',4',5'-trimethoxychalcone
• CAS: 133707-53-6
• 化学式: C₁₈H₁₇NO₆
• 分子量: 343.336
• InChiKey: PGLMCDFGQNAYCR-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190 °C
• 沸点：
  510.3±50.0 °C(predicted)
• 密度：
  1.254±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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：

  3-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 tin(II) chloride dihdyrate 、 copper diacetate 、 sodium hydride 、 三乙胺 作用下， 以 乙醚 、 二甲基亚砜 、 乙酸乙酯 、 1,2-二氯乙烷 、 mineral oil 为溶剂， 反应 28.0h， 生成 (4-(4-aminophenyl)-1-phenyl-1H-pyrrol-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  3-Aroyl-1,4-diarylpyrroles Inhibit Chronic Myeloid Leukemia Cell Growth through an Interaction with Tubulin

  摘要：

  We designed 3-aroyl-1,4-diarylpyrrole (ARDAP) derivatives as potential anticancer agents having different substituents at the 1- or 4 -phenyl ring. ARDAP compounds exhibited potent inhibition of tubulin polymerization, binding of colchicine to tubulin, and cancer cell growth. ARDAP derivative 10 inhibited the proliferation of BCR/ABL-expressing KU812 and LAMA84 cells from chronic myeloid leukemia (CML) patients in blast crisis and of hematopoietic cells ectopically expressing the imatinib mesylate (IM) -sensitive KBM5-WT or its IM -resistant KBM5-T315I mutation. Compound 10 minimally affected the proliferation of normal blood cells, indicating that it may be a promising agent to overcome broad tyrosine kinase inhibitor resistance in relapsed/refractory CML patients. Compound 10 significantly decreased CML proliferation by inducing G2/M phase arrest and apoptosis via a mitochondria-dependent pathway. ARDAP 10 augmented the cytotoxic effects of IM in human CML cells. Compound 10 represents a robust lead compound to develop tubulin inhibitors with potential as novel treatments for CML.

  DOI：

  10.1021/acsmedchemlett.7b00022
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 对硝基苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以93%的产率得到3-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  3-Arylindanones和相关化合物可作为抗结直肠癌的抗增殖剂。

  摘要：

  合成了多种亚苄基茚满酮及其衍生物作为抗癌剂。其中的两个类似物，即7和22，表现出对几种人类癌细胞系的显着抗增殖活性。这两种化合物都具有抗有丝分裂活性，并通过激活caspase途径在DLD1大肠腺癌细胞中诱导凋亡。在细胞周期分析中，这两种化合物在DLD1细胞中主要诱导G2 / M期停滞。分子对接研究表明，化合物7占据了β-微管蛋白的秋水仙碱结合口袋。两种化合物在啮齿动物的急性口服毒性方面都是安全的。两种化合物都被进一步优化以获得更好的功效。

  DOI：

  10.1111/cbdd.13574

文献信息

• Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted
  作者：Daniela Batovska、Stoyan Parushev、Bistra Stamboliyska、Iva Tsvetkova、Mariana Ninova、Hristo Najdenski

  DOI：10.1016/j.ejmech.2008.05.010

  日期：2009.5

  A large series of chalcones were synthesized and studied against Staphylococcus aureus and Escherichia coli. Chalcones were either unsubstituted in ring A or possessed 4-chloro or 3',4',5'-trimethoxy groups. Their other ring B was variously substituted. It was found that the antistaphylococcal activity of chalcones was related to the energy difference between the two highest occupied molecular orbitals (HOMO and HOMO-1). Presence of hydroxyl group in ring B was not a determinant factor for the anti-staphylococcal activity, but the lipophilicity of ring A of the hydroxyl chalcones was of importance. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Identification of 3′,4′,5′-trimethoxychalcone analogues as potent inhibitors of Helicobacter pylori-induced inflammation in human gastric epithelial cells
  作者：Chih-Ho Lai、Yerra Koteswara Rao、Shih-Hua Fang、Yu-Ting Sing、Yew-Min Tzeng

  DOI：10.1016/j.bmcl.2010.07.094

  日期：2010.9

  Efforts to identify potent small molecule inhibitors of Helicobacter pylori led to the evaluation of 23 3',4',5'-trimethoxychalcone analogues. Some of the compounds displayed potent antibacterial activity against H. pylori. Three most active and selective compounds 1, 7, and 13 also showed the bactericide activity against the reference as well as multidrug-resistant strains of H. pylori. Additionally, the aforementioned three compounds potentially inhibited the H. pylori adhesion and invasion to human gastric epithelial (AGS) cells. Furthermore, these selective compounds inhibited the H. pylori-induced gastric inflammation by reduced inflammatory mediator's nuclear factor kappa B activation, and the secretion of interleukin-8. (c) 2010 Elsevier Ltd. All rights reserved.
• 3-Aroyl-1,4-diarylpyrroles Inhibit Chronic Myeloid Leukemia Cell Growth through an Interaction with Tubulin
  作者：Giuseppe La Regina、Ruoli Bai、Antonio Coluccia、Valeria Famiglini、Sara Passacantilli、Valentina Naccarato、Giorgio Ortar、Carmela Mazzoccoli、Vitalba Ruggieri、Francesca Agriesti、Claudia Piccoli、Tiziana Tataranni、Marianna Nalli、Andrea Brancale、Stefania Vultaggio、Ciro Mercurio、Mario Varasi、Concetta Saponaro、Sara Sergio、Michele Maffia、Addolorata Maria Luce Coluccia、Ernest Hamel、Romano Silvestri

  DOI：10.1021/acsmedchemlett.7b00022

  日期：2017.5.11

  We designed 3-aroyl-1,4-diarylpyrrole (ARDAP) derivatives as potential anticancer agents having different substituents at the 1- or 4 -phenyl ring. ARDAP compounds exhibited potent inhibition of tubulin polymerization, binding of colchicine to tubulin, and cancer cell growth. ARDAP derivative 10 inhibited the proliferation of BCR/ABL-expressing KU812 and LAMA84 cells from chronic myeloid leukemia (CML) patients in blast crisis and of hematopoietic cells ectopically expressing the imatinib mesylate (IM) -sensitive KBM5-WT or its IM -resistant KBM5-T315I mutation. Compound 10 minimally affected the proliferation of normal blood cells, indicating that it may be a promising agent to overcome broad tyrosine kinase inhibitor resistance in relapsed/refractory CML patients. Compound 10 significantly decreased CML proliferation by inducing G2/M phase arrest and apoptosis via a mitochondria-dependent pathway. ARDAP 10 augmented the cytotoxic effects of IM in human CML cells. Compound 10 represents a robust lead compound to develop tubulin inhibitors with potential as novel treatments for CML.
• 3‐Arylindanones and related compounds as antiproliferative agents against colorectal cancer
  作者：Ankita Srivastava、Kusumoori Ravi、Kaneez Fatima、Mayank Maheshwari、Raghib Ashraf、Mohammad Hasanain、Pankaj Yadav、Hina Iqbal、Yogesh Kumar、Suaib Luqman、Debabrata Chanda、Feroz Khan、Karuna Shanker、Jayanta Sarkar、Arvind Singh Negi

  DOI：10.1111/cbdd.13574

  日期：2019.9

  derivatives were synthesized as anticancer agents. Two of the analogues, that is 7 and 22, exhibited significant antiproliferative activity against several human cancer cell lines. Both the compounds possessed antimitotic activity and induced apoptosis in DLD1 colorectal adenocarcinoma cells through activation of caspase pathways. In cell cycle analysis, both the compounds induced predominantly G2/M phase arrest

  合成了多种亚苄基茚满酮及其衍生物作为抗癌剂。其中的两个类似物，即7和22，表现出对几种人类癌细胞系的显着抗增殖活性。这两种化合物都具有抗有丝分裂活性，并通过激活caspase途径在DLD1大肠腺癌细胞中诱导凋亡。在细胞周期分析中，这两种化合物在DLD1细胞中主要诱导G2 / M期停滞。分子对接研究表明，化合物7占据了β-微管蛋白的秋水仙碱结合口袋。两种化合物在啮齿动物的急性口服毒性方面都是安全的。两种化合物都被进一步优化以获得更好的功效。