3-(3-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 428849-24-5

• 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-(3-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 428849-24-5
• 化学式: C₁₈H₁₇NO₆
• 分子量: 343.336
• InChiKey: MQEHSCIECKRQOX-UHFFFAOYSA-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：

  3-(3-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 copper diacetate 、 sodium hydride 、 三乙胺 作用下， 以 乙醚 、 二甲基亚砜 、 1,2-二氯乙烷 、 mineral oil 为溶剂， 反应 22.0h， 生成 (4-(3-nitrophenyl)-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 、 间硝基苯甲醛 在 lithium hydroxide monohydrate 作用下， 以 乙醇 为溶剂， 以67.4%的产率得到3-(3-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  METHOXYCHALCONE DERIVATIVES AND USES THEREOF

  摘要：

  提供具有抗癌活性的甲氧基胆烷衍生物。

  公开号：

  US20210347724A1

文献信息

• METHOXYCHALCONE DERIVATIVES AND USES THEREOF
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20210347724A1

  公开（公告）日：2021-11-11

  Methoxychalone derivatives with anti-cancer activity are provided.

  提供具有抗癌活性的甲氧基胆烷衍生物。
• Anti-proliferative potential of triphenyl substituted pyrimidines against MDA-MB-231, HCT-116 and HT-29 cancer cell lines
  作者：Ashish Ranjan Dwivedi、Vijay Kumar、Harmeet Kaur、Naveen Kumar、Ravi Prakash Yadav、Ramarao Poduri、Somesh Baranwal、Vinod Kumar

  DOI：10.1016/j.bmcl.2020.127468

  日期：2020.10

  A series of triphenyl substituted pyrimidines as analogous of colchicine and combretastatin A-4 was synthesized and evaluated for the antiproliferative potential. The compounds were screened against MDA-MB-231, HCT-116 and HT-29 cell lines using MTT assay. Most of the compounds displayed antiproliferative activity in low to sub micro molar concentration. Amongst the synthesized derivatives, compounds HK-2, HK-10 and HK-13 were found to be effective against all the three cancer cell lines. HK-2 exhibited IC50 values of 3.39 mu M, 4.78 mu M and 4.23 mu M, HK-10 showed IC50 values of 0.81 mu M, 5.89 mu M, 4.96 mu M and HK-13 showed IC50 values 3.24 mu M, 4.93 mu M and 4.73 mu M against MDA-MB-231, HCT-116 and HT-29 cancer cell lines, respectively. HK-10 was found to be the most potent compound in the series with IC50 values of 0.81 mu M against MDA-MB-231. In the cell cycle analysis, HK-2 and HK-10 showed cell arrest at G2/M phase of the cell cycle while HK-13 inhibited cell growth at the G1/G0 phase. All the three compounds showed cell death induced through apoptosis. In the docking studies, HK-2, HK-10 and HK-13 were found to fit well in the colchicine binding site of the tubulin. Some of the compounds in the current series were found to be promising against all the three cancer cell lines and may act as potent leads for further development.
• Synthesis and biological evaluation of a series of tangeretin-derived chalcones
  作者：Jérôme Quintin、Julie Desrivot、Sylviane Thoret、Patrick Le Menez、Thierry Cresteil、Guy Lewin

  DOI：10.1016/j.bmcl.2008.10.126

  日期：2009.1

  A series of chalcones polyoxygenated on the ring A ( with pentamethoxy or 2''-hydroxy-3',4',5',6'-tetramethoxy substitution patterns) was synthesized from tangeretin, a natural Citrus flavonoid. These chalcones were evaluated for their antiproliferative, activation of apoptosis, inhibition of tubulin assembly and antileishmanial activities. Comparison with the reference analogous 3',4',5'-trimethoxylated chalcones showed that such peroxygenated substitution patterns on the ring A were less beneficial to these activities. (C) 2008 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.