3-(3-Hydroxy-4-methoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one | 121405-62-7

• 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-Hydroxy-4-methoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 121405-62-7
• 化学式: C₁₇H₁₆O₄
• mdl: MFCD04687227
• 分子量: 284.312
• InChiKey: PQWVNPAFNRAECC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(3-Hydroxy-4-methoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 2-methoxy-5-(2-(8-methoxy-1H-naphtho[1,2-e][1,3]oxazin-2(3H)-yl)-6-(4-methoxyphenyl)pyrimidin-4-yl)phenol
  参考文献：
  名称：

  Design, synthesis, docking studies and biological screening of 2-pyrimidinyl-2, 3-dihydro-1 H -naphtho [1, 2- e ][1, 3] oxazines as potent tubulin polymerization inhibitors

  摘要：

  DOI：

  10.1080/07391102.2023.2266766
• 作为产物：
  描述：

  异香兰素 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 3-(3-Hydroxy-4-methoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  新的2-（3-（4-（4-甲氧苯基））5-（芳基）-4,5-二氢-1H-吡唑-1-基）苯并[d]噻唑衍生物的合成，细胞毒性和碳酸酐酶抑制作用

  摘要：

  除1b和1b以外，首次合成了2-（3- [4-甲氧基苯基] -5-芳基-4,5-二氢-1 H-吡唑-1-基）苯并[ d ]噻唑（1b-7b）。光谱方法，例如1 H NMR，13 C NMR和HRMS被用于阐明合成化合物的化学结构。苯基（1b），2-甲氧基苯基（2b），4-甲氧基苯基（3b），4-甲氧基-3-羟基苯基（4b），2,5-二甲氧基苯基（5b），3,4,5-三甲氧基苯基（6b），或噻吩-2-基（7b）用作芳基部分。评估了化合物对人碳酸酐酶I和II酶（hCA I和hCA II）的抑制作用。所述化合物对人类口腔鳞状细胞癌和人类正常口腔细胞的体外细胞毒性作用通过MTT进行。化合物（1b-7b）的Ki值为36.87±11.62-66.24±2.99μM（hCA I）和22.66±1.41-89.95±6.25μM（hCA II）。朝向hCA I的化合物1b（Ki = 36.87±11.62μM

  DOI：

  10.1002/jhet.3985

文献信息

• Structure−Activity Relationship Studies of Chalcone Leading to 3-Hydroxy-4,3′,4′,5′-tetramethoxychalcone and Its Analogues as Potent Nuclear Factor κB Inhibitors and Their Anticancer Activities
  作者：Balasubramanian Srinivasan、Thomas E. Johnson、Rahul Lad、Chengguo Xing

  DOI：10.1021/jm901278z

  日期：2009.11.26

  Chalcone is a privileged structure, demonstrating promising anti-inflammatory and anticancer activities. One potential mechanism is to suppress nuclear factor kappa B (NF-kappa B) activation. The structures of chalcone-based NF-kappa B inhibitors vary significantly that there is minimum information about their structure-activity relationships (SAR). This study aims to establish SAR of chalcone-based compounds to NF-kappa B inhibition, to explore the feasibility of developing simple chalcone-based potent NF-kappa B inhibitors, and to evaluate their anticancer activities. Three series of chalcones were synthesized in one to three steps with the key step being aldol condensation. These candidates demonstrated a wide range of NF-kappa B inhibitory activities, some of low micromolar potency, establishing that structural complexity is not required for NF-kappa B inhibition. Lead compounds also demonstrate potent cytotoxicity against lung cancer cells. Their cytotoxicities correlate moderately well with their NF-kappa B inhibitory activities, suggesting that suppressing NF-kappa B activation is likely responsible for at least some of the cytotoxicities. One lead compound effectively inhibits lung tumor growth with no signs of adverse side effects.
• A convenient synthesis of cis-restricted combretastatin analogues with pyrazole and isoxazole cores
  作者：Dmitry V. Tsyganov、Marina N. Semenova、Leonid D. Konyushkin、Vladimir I. Ushkarov、Mikhail M. Raihstat、Victor V. Semenov

  DOI：10.1016/j.mencom.2019.03.015

  日期：2019.3

  A series of combretastatin analogues, diarylpyrazoles and diarylisoxazoles, have been synthesized and evaluated for their antimitotic tubulin-binding activity using the phenotypic sea urchin (Paracentrotus lividus) embryo assay. One pyrazole analogue and four isoxazole analogues have been identified as potent antimitotic agents comparable with combretastatins A-2 and A-4, with the lowest observable effective concentration of 1-10 nmol dm(-3) for cleavage alteration of the test embryos.