3,5,4'-trichloro-2-hydroxy-trans-chalcone | 93203-72-6

• 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: 3,5,4'-trichloro-2-hydroxy-trans-chalcone
• 英文别名: 3,5,4'-Trichlor-2-hydroxy-trans-chalkon；1-(4-chlorophenyl)-3-(3,5-dichloro-2-hydroxyphenyl)prop-2-en-1-one；(E)-1-(4-chlorophenyl)-3-(3,5-dichloro-2-hydroxyphenyl)prop-2-en-1-one
• CAS: 93203-72-6
• 化学式: C₁₅H₉Cl₃O₂
• 分子量: 327.594
• InChiKey: OKNNLFRSPKBEKD-ZZXKWVIFSA-N

物化性质

• 沸点：
  480.0±45.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5,4'-trichloro-2-hydroxy-trans-chalcone 在 potassium tert-butylate 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 13.0h， 生成 3-(4-chlorophenyl)-5-(3,5-dichloro-2-(2,6-dinitro-4-(trifluoromethyl)phenoxy)phenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Synthesis, and antibacterial activity of novel 4,5-dihydro-1H-pyrazole derivatives as DNA gyrase inhibitors

  摘要：

  设计并合成了一系列含有二硝基苯三氟甲烷结构单元的4,5-二氢吡唑衍生物（4a–4t）作为DNA旋转酶抑制剂。基于初步结果，4d、4h和4t化合物对细菌生长具有强大的抑制活性，可能是优秀的抗菌剂；其中，化合物4t显示出最强的活性，其最低抑制浓度（MIC）值分别为3.125、0.39、0.39和0.39 μg mL−1，分别对抗枯草芽孢杆菌、金黄色葡萄球菌、铜绿假单胞菌和肠道杆菌，与青霉素和卡那霉素B的相应MIC值3.125、3.125、0.39、0.39 μg mL−1和1.562、1.562、1.562、1.562 μg mL−1相当。特别是，化合物4d对测试的革兰氏阳性细菌显示出最强的抗菌活性，MIC值为0.39 μg mL−1，并且对枯草芽孢杆菌DNA旋转酶和金黄色葡萄球菌DNA旋转酶的抑制活性最强，IC50为0.125 μg mL−1。进行对接模拟，将化合物4d插入金黄色葡萄球菌DNA旋转酶的活性位点，以确定可能的结合构象。

  DOI：

  10.1039/c3ob41953c
• 作为产物：
  描述：

  对氯苯乙酮 、 3,5-二氯水杨醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3,5,4'-trichloro-2-hydroxy-trans-chalcone
  参考文献：
  名称：

  Synthesis, and antibacterial activity of novel 4,5-dihydro-1H-pyrazole derivatives as DNA gyrase inhibitors

  摘要：

  设计并合成了一系列含有二硝基苯三氟甲烷结构单元的4,5-二氢吡唑衍生物（4a–4t）作为DNA旋转酶抑制剂。基于初步结果，4d、4h和4t化合物对细菌生长具有强大的抑制活性，可能是优秀的抗菌剂；其中，化合物4t显示出最强的活性，其最低抑制浓度（MIC）值分别为3.125、0.39、0.39和0.39 μg mL−1，分别对抗枯草芽孢杆菌、金黄色葡萄球菌、铜绿假单胞菌和肠道杆菌，与青霉素和卡那霉素B的相应MIC值3.125、3.125、0.39、0.39 μg mL−1和1.562、1.562、1.562、1.562 μg mL−1相当。特别是，化合物4d对测试的革兰氏阳性细菌显示出最强的抗菌活性，MIC值为0.39 μg mL−1，并且对枯草芽孢杆菌DNA旋转酶和金黄色葡萄球菌DNA旋转酶的抑制活性最强，IC50为0.125 μg mL−1。进行对接模拟，将化合物4d插入金黄色葡萄球菌DNA旋转酶的活性位点，以确定可能的结合构象。

  DOI：

  10.1039/c3ob41953c

文献信息

• Small-molecule modulators of hepatocyte growth factor / scatter factor activities
  申请人：——

  公开号：US20030045559A1

  公开（公告）日：2003-03-06

  The invention is directed to small organic molecules having the ability to mimic or agonize hepatocyte growth factor/scatter factor (HGF/SF) activity, or inhibit or antagonize HGF/SF activity, the former useful for promoting, for example, vascularization of tissues or organs for promoting wound or tissue healing, or augmenting or restoring blood flow to ischemic tissues such as the heart following myocardial infarction. Inhibition of cellular growth or proliferation is beneficial in the treatment, for example, of inflammatory diseases such as inflammatory joint and skin diseases, and dysproliferative diseases such as cancer.

  该发明涉及具有模拟或激活肝细胞生长因子/散发因子（HGF/SF）活性的小有机分子，或抑制或拮抗HGF/SF活性的能力，前者可用于促进组织或器官的血管化，促进伤口或组织愈合，或增强或恢复缺血组织（例如心肌梗死后的心脏）的血流。细胞生长或增殖的抑制对于治疗炎症性疾病（如炎性关节和皮肤疾病）和增殖异常性疾病（如癌症）是有益的。
• Small-molecule modulators of hepatocyte growth factor/scatter factor activities
  申请人：Pillarisetti Sivaram

  公开号：US20050096372A1

  公开（公告）日：2005-05-05

  The invention is directed to small organic molecules having the ability to mimic or agonize hepatocyte growth factor/scatter factor (HGF/SF) activity, or inhibit or antagonize HGF/SF activity, the former useful for promoting, for example, vascularization of tissues or organs for promoting wound or tissue healing, or augmenting or restoring blood flow to ischemic tissues such as the heart following myocardial infarction. Inhibition of cellular growth or proliferation is beneficial in the treatment, for example, of inflammatory diseases such as inflammatory joint and skin diseases, and dysproliferative diseases such as cancer.

  本发明涉及具有模拟或激动肝细胞生长因子/散射因子（HGF/SF）活性，或抑制或拮抗 HGF/SF 活性的有机小分子，前者可用于促进组织或器官的血管化，以促进伤口或组织愈合，或增加或恢复缺血组织（如心肌梗塞后的心脏）的血流量。抑制细胞生长或增殖有利于治疗炎症性疾病（如关节炎和皮肤病）和增殖障碍性疾病（如癌症）等。
• Design, synthesis and biological evaluation of novel chalcone derivatives as antitubulin agents
  作者：Hui Zhang、Jia-Jia Liu、Jian Sun、Xian-Hui Yang、Ting-Ting Zhao、Xiang Lu、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.03.055

  日期：2012.5

  A series of novel chalcone derivatives have been designed and synthesized, and their biological activities were also evaluated as potential inhibitors of tubulin. These compounds were assayed for growth-inhibitory activity against MCF-7 and A549 cell lines in vitro. Compound 3d showed the most potent antiproliferative activity against MCF-7 and A549 cell lines with IC50 values of 0.03 and 0.95 mu g/mL and exhibited the most potent tubulin inhibitory activity with IC50 of 1.42 mu g/mL. Docking simulation was performed to insert compound 3d into the crystal structure of tubulin at colchicines binding site to determine the probable binding model. Based on the preliminary results, compound 3d with potent inhibitory activity in tumor growth may be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.
• 275. Comparison of the directive powers of elements having consecutive atomic numbers. Part III. Nitration of halogeno-2-phenylbenzopyrylium salts
  作者：Catherine G. Le Fèvre、R. J. W. Le Fèvre

  DOI：10.1039/jr9320001988

  日期：——
• OSMAN, S. A. M.;HAMMAD, M.;SWELLEM, R. H.;EL-BAYOUKI, K. A. M., EGYPT. J. CHEM., 30,(1987) N, C. 481-490
  作者：OSMAN, S. A. M.、HAMMAD, M.、SWELLEM, R. H.、EL-BAYOUKI, K. A. M.

  DOI：——

  日期：——