3-(3,5-Dichloro-2-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one | 1398523-50-6

• 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-(3,5-Dichloro-2-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 1398523-50-6
• 化学式: C₁₆H₁₂Cl₂O₃
• 分子量: 323.175
• InChiKey: BKFJYXAVEXIXNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,5-Dichloro-2-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one 在 1-羟基苯并三唑 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-(5-(3,5-dichloro-2-hydroxyphenyl)-3-(p-methoxyphenyl)-4,5-dihydro-1H-1-pyrazolyl)ethanone
  参考文献：
  名称：

  Synthesis, biological evaluation of novel 4,5-dihydro-2H-pyrazole 2-hydroxyphenyl derivatives as BRAF inhibitors

  摘要：

  A series of novel 4,5-dihydropyrazole derivatives (3a-3t) containing hydroxyphenyl moiety as potential V600E mutant BRAF kinase (BRAF(V600E)) inhibitors were designed and synthesized. Docking simulation was performed to insert compounds 3d (1-(5-(5-chloro-2-hydroxyphenyl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) and 3m (1-(3-(4-chlorophenyl)-5-(3,5-dibromo-2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) into the crystal structure of BRAF(V600E) to determine the probable binding model, respectively. Based on the preliminary results, compound 3d and 3m with potent inhibitory activity in tumor growth may be a potential anticancer agent. Results of the bioassays against BRAF(V600E), MCF-7 human breast cancer cell line and WM266.4 human melanoma cell line all showed several compounds had potent activities IC50 value in low micromolar range, among them, compound 3d and compound 3m showed strong potent anticancer activity, which were proved by that 3d: IC50 = 1.31 mu M for MCF-7 and IC50 = 0.45 mu M for WM266.5, IC50 = 0.22 mu M for BRAF(V600E), 3m: IC50 = 0.97 mu M for MCF-7 and IC50 = 0.72 mu M for WM266.5, IC50 = 0.46 mu M for BRAF(V600E), which were comparable with the positive control Erlotinib. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.020
• 作为产物：
  描述：

  对甲氧基苯乙酮 、 3,5-二氯水杨醛 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3-(3,5-Dichloro-2-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  作为潜在琥珀酸脱氢酶抑制剂的新型 4H-Chromene 类似物的设计、合成、生物学评价和分子建模

  摘要：

  设计合成了31个新的4 H-色烯衍生物。它们的结构已通过 IR、1 H NMR、13 C NMR 和 HRMS进行鉴定。化合物2a的晶体结构由单晶X射线衍射确定。对它们的抗真菌活性进行了评价，包括Pyricularia oryzae、Erysiphe graminis、Coniella diplodiella、Pseudoperonospora cubensis和Sclerotinia sclerotiorum。这些结果表明，大多数化合物在 20 μg/mL 时表现出显着的抑制活性。化合物4b和4c对核盘菌显示出优异的抗真菌活性，并且比氟吡菌酰胺具有更好的功效。同时，评估了生物活性化合物对琥珀酸脱氢酶 (SDH) 的抑制活性。结果表明，这些化合物具有突出的活性。化合物4b和4c显示出比氟吡菌酰胺更好的抑制活性。分子模拟结果表明，化合物4c对SDH的亲和力强于氟吡菌酰胺。这是首次报道4 H-色烯类似物对

  DOI：

  10.1021/acs.jafc.1c03304

文献信息

• Stereoselective Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives via a Sequential Michael Addition/Bicyclization Reaction
  作者：Guodong Yin、Tianbing Ren、Yin Rao、Yifan Zhou、Zhexian Li、Wenming Shu、Anxin Wu

  DOI：10.1021/jo400081q

  日期：2013.4.5

  A highly efficient and stereoselective synthesis of coumarin-, 1,3-cyclohexanedione-, and 1,4-naphthoquinone-fused 2,8-dioxabicyclo[3.3.1]nonanes is described. This was achieved via a sequential Michael addition/bicyclization reaction from easily accessible 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one derivatives. Three chemical bonds (one C–C bond and two C–O bonds), two six-membered cycles, and two

  描述了香豆素-，1,3-环己二酮-和1,4-萘醌稠合的2,8-二氧杂双环[3.3.1]壬烷的高效和立体选择性合成。这是通过从容易获得的3-（2-羟苯基）-1-苯基丙-2-烯-1-酮衍生物通过顺序迈克尔加成/二环化反应实现的。一锅操作中形成了三个化学键（一个C–C键和两个C–O键），两个六元循环和两个立体中心。
• 苯并吡喃类化合物及其在农药中的用途
  申请人：西华大学

  公开号：CN113004240B

  公开（公告）日：2023-02-03

  本发明涉及苯并吡喃类化合物及其在农药中的用途，属于农药技术领域。本发明解决的技术问题是提供一种可作为杀虫剂和杀菌剂使用的苯并吡喃类化合物。本发明苯并吡喃类化合物的结构通式为式I所示，其中，R1为氢原子、卤素原子、C1‑C4烷基或C1‑C4烷氧基；R2为氢原子、卤素原子、C1‑C4烷基或C1‑C4烷氧基。本发明化合物的合成过程简单，对害虫有较好的毒杀效果，对植物病原细菌有较好的抑制作用，为新农药的创制奠定了较好的基础。
• Synthesis, biological evaluation of novel 4,5-dihydro-2H-pyrazole 2-hydroxyphenyl derivatives as BRAF inhibitors
  作者：Jia-Jia Liu、Hui Zhang、Juan Sun、Zhong-Chang Wang、Yu-Shun Yang、Dong-Dong Li、Fei Zhang、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.08.020

  日期：2012.10

  A series of novel 4,5-dihydropyrazole derivatives (3a-3t) containing hydroxyphenyl moiety as potential V600E mutant BRAF kinase (BRAF(V600E)) inhibitors were designed and synthesized. Docking simulation was performed to insert compounds 3d (1-(5-(5-chloro-2-hydroxyphenyl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) and 3m (1-(3-(4-chlorophenyl)-5-(3,5-dibromo-2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) into the crystal structure of BRAF(V600E) to determine the probable binding model, respectively. Based on the preliminary results, compound 3d and 3m with potent inhibitory activity in tumor growth may be a potential anticancer agent. Results of the bioassays against BRAF(V600E), MCF-7 human breast cancer cell line and WM266.4 human melanoma cell line all showed several compounds had potent activities IC50 value in low micromolar range, among them, compound 3d and compound 3m showed strong potent anticancer activity, which were proved by that 3d: IC50 = 1.31 mu M for MCF-7 and IC50 = 0.45 mu M for WM266.5, IC50 = 0.22 mu M for BRAF(V600E), 3m: IC50 = 0.97 mu M for MCF-7 and IC50 = 0.72 mu M for WM266.5, IC50 = 0.46 mu M for BRAF(V600E), which were comparable with the positive control Erlotinib. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, Synthesis, Biological Evaluation, and Molecular Modeling of Novel 4<i>H</i>-Chromene Analogs as Potential Succinate Dehydrogenase Inhibitors
  作者：Tong Lu、Yingkun Yan、Tingting Zhang、Guilan Zhang、Tingting Xiao、Wei Cheng、Wenjing Jiang、Jingwen Wang、Xiaorong Tang

  DOI：10.1021/acs.jafc.1c03304

  日期：2021.9.15

  exhibited remarkable inhibitory activities at 20 μg/mL. Compounds 4b and 4c displayed excellent antifungal activity against S. sclerotiorum and possessed better efficacy than fluopyram. At the same time, the inhibitory activity of the bioactive compounds was evaluated against succinate dehydrogenase (SDH). The results showed that these compounds possessed outstanding activity. Compounds 4b and 4c displayed

  设计合成了31个新的4 H-色烯衍生物。它们的结构已通过 IR、1 H NMR、13 C NMR 和 HRMS进行鉴定。化合物2a的晶体结构由单晶X射线衍射确定。对它们的抗真菌活性进行了评价，包括Pyricularia oryzae、Erysiphe graminis、Coniella diplodiella、Pseudoperonospora cubensis和Sclerotinia sclerotiorum。这些结果表明，大多数化合物在 20 μg/mL 时表现出显着的抑制活性。化合物4b和4c对核盘菌显示出优异的抗真菌活性，并且比氟吡菌酰胺具有更好的功效。同时，评估了生物活性化合物对琥珀酸脱氢酶 (SDH) 的抑制活性。结果表明，这些化合物具有突出的活性。化合物4b和4c显示出比氟吡菌酰胺更好的抑制活性。分子模拟结果表明，化合物4c对SDH的亲和力强于氟吡菌酰胺。这是首次报道4 H-色烯类似物对