1,3-bis(3-hydroxyphenyl)prop-2-en-1-one | 142784-23-4

• 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: 1,3-bis(3-hydroxyphenyl)prop-2-en-1-one
• 英文别名: 3,3'-Dihydroxy-chalkon；1,3-bis(3-hydroxyphenyl)-2-propen-1-one
• CAS: 142784-23-4
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: UALHWTHYPDBXSN-UHFFFAOYSA-N

物化性质

• 沸点：
  492.6±45.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bis(3-hydroxyphenyl)prop-2-en-1-one 、 1-[2-oxo-2-(thiophen-2-yl)ethyl]pyridinium iodide 在 ammonium acetate 、 溶剂黄146 作用下， 以85.6%的产率得到3,3'-[6-(thiophen-2-yl)pyridine-2,4-diyl]diphenol
  参考文献：
  名称：

  Discovery of dihydroxylated 2,4-diphenyl-6-thiophen-2-yl-pyridine as a non-intercalative DNA-binding topoisomerase II-specific catalytic inhibitor

  摘要：

  We describe our rationale for designing specific catalytic inhibitors of topoisomerase II (topo II) over topoisomerase I (topo I). Based on 3D-QSAR studies of previously published dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives, 9 novel dihydroxylated 2,4-diphenyl-6-thiophen-2-yl pyridine compounds were designed, synthesized, and their biological activities were evaluated. These compounds have 2-thienyl ring substituted on the R(3) group on the pyridine ring and they all showed excellent specificity toward topo II compared to topo I. In vitro experiments were performed for compound 13 to determine the mechanism of action for this series of compounds. Compound 13 inhibited topoisomerase II specifically by non-intercalative binding to DNA and did not stabilize enzyme-cleavable DNA complex. Compound 13 efficiently inhibited cell viability, cell migration, and induced G1 arrest. Also from 3D-QSAR studies, the results were compared with other previously published dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives to explain the structure-activity relationships.

  DOI：

  10.1016/j.ejmech.2014.04.066
• 作为产物：
  描述：

  3-羟基苯乙酮 、 间羟基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 1,3-bis(3-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  固相微波法对查耳酮类新嘧啶-2（1H）-醇/硫醇衍生物的生物学评价和合成

  摘要：

  通过以下反应合成了二十五个新的羟基和甲氧基取代的4,6-二芳基嘧啶-2（1H）-醇（20-34）和4,6-二芳基嘧啶-2（1H）-硫醇衍生物（35-44）。使用固相微波方法，将相应的1,3-二芳基-2-丙烯-1酮化合物（1-19）与尿素或硫脲一起使用。对所有新的合成化合物（20-44）的α-葡萄糖苷酶活性进行了评估。但是，只有化合物22–25、27、31、34、35、37和40表现出比标准阿卡波糖更大的抑制作用。活性化合物的IC50值在2.36和13.34μM之间。还筛选了25种新化合物的体外胰腺脂肪酶活性，发现化合物20–27和35–39具有活性。在这些化合物中，26、27和39在0.40±0.06、0.26±0.07，和0.29±0.026μM。对所有新化合物（20-44）的九种测试微生物的体外抗菌活性进行了评估。经测定，化合物20-24和35-39在检测的细菌病原菌中对革兰氏阳性粪便

  DOI：

  10.3906/kim-1711-9

文献信息

• Miquel,J.F., Bulletin de la Societe Chimique de France, 1961, p. 1369 - 1376
  作者：Miquel,J.F.

  DOI：——

  日期：——
• Dihydroxylated 2,4,6-triphenyl pyridines: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship study
  作者：Radha Karki、Pritam Thapa、Han Young Yoo、Tara Man Kadayat、Pil-Hoon Park、Youngwha Na、Eunyoung Lee、Kyung-Hwa Jeon、Won-Jea Cho、Heesung Choi、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2012.01.015

  日期：2012.3

  Twelve dihydroxylated 2,4,6-triphenyl pyridines were designed and synthesized which contain hydroxyl groups at ortho, meta or para position of 2- and 6-phenyl, or 2- and 4-phenyl rings attached to the central pyridine. They were evaluated for topoisomerase I and II inhibitory activity, and cytotoxicity against several human cancer cell lines for the development of novel anticancer agents. Generally, dihydroxylated 2,4,6-triphenyl pyridines exhibited stronger topoisomerase II inhibitory activity, and cytotoxicity compared to those of monohydroxylated 2,4,6-triphenyl pyridines. The concrete structure-activity relationship was observed that dihydroxylated 2,4,6-triphenyl pyridines with hydroxyl group at meta or para position of 2-phenyl ring displayed significant topoisomerase II inhibitory activity as well as cytotoxicity. Positive correlation between topoisomerase II inhibitory activity and cytotoxicity was observed for compounds 10, 12, 13, 17-20 and 22. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Hydroxychalcones as Potential Anti-Angiogenic Agent
  作者：Radha Karki、You-Ra Kang、Chul-Hoon Kim、Kyung-Sook Kwak、Jung-Ae Kim、Eung-Seok Lee

  DOI：10.5012/bkcs.2012.33.9.2925

  日期：2012.9.20
• Synthesis and biological activity of 2,4-di-p-phenolyl-6-2-furanyl-pyridine as a potent topoisomerase II poison
  作者：Radha Karki、Chanmi Park、Kyu-Yeon Jun、Tara Man Kadayat、Eung-Seok Lee、Youngjoo Kwon

  DOI：10.1016/j.ejmech.2014.11.045

  日期：2015.1

  Dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives were simply achieved using Claisen Schmidt condensation reaction and modified Krohnke pyridine synthetic method. Total forty-five compounds were designed and synthesized which contain hydroxyl groups at artho, meta or para position of 2- and 4-phenyl rings attached to the central pyridine. They were evaluated for topoisomerase I and II inhibitory activity, and cytotoxicity against several human cancer cell lines for the development of novel antitumor agents. Most of the prepared compounds exhibited significant antiproliferative activity on human cancer cell lines, HCT15 and K562, as well as potent topo II inhibitory activity comparable to or stronger than etoposide. The structure activity relationship demonstrated that compounds with hydroxyl group at meta or para position of 2-phenyl ring in combination with hydroxyl at ortho, meta or para position of 4-phenyl ring displayed the most potent topoisomerase II inhibitory activity and cytotoxicity. Positive correlation between topoisomerase II inhibition and cytotoxicity was obtained for several compounds (30, 35, 36, 40-45, 49, 54, 56). Compound 56 showed the most potent topoisomerase H inhibitory activity at low concentration and functioned as a topoisomerase poison like the mode of action of etoposide. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Baseer, Muhammad; Saeed, Aanier; Samra, Shahid A., Journal of the Indian Chemical Society, 2013, vol. 90, # 6, p. 857 - 862
  作者：Baseer, Muhammad、Saeed, Aanier、Samra, Shahid A.、Ashraf, Zaman、Ansari, Farzana L.

  DOI：——

  日期：——