(E)-3-(2-chlorophenyl)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)prop-2-en-1-one | 861107-97-3

• 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: (E)-3-(2-chlorophenyl)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: 2-chloro-2'-hydroxy-4',6'-dimethoxychalcone；2-Chloro-4',6'-dimethoxy-2'-hydroxychalcone；(E)-3-(2-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
• CAS: 861107-97-3
• 化学式: C₁₇H₁₅ClO₄
• 分子量: 318.757
• InChiKey: YZXFAXZRQRCABV-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-chlorophenyl)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)prop-2-en-1-one 在 盐酸 、 硫酸 、 碘 作用下， 以 水 、 二甲基亚砜 、 异丙醇 为溶剂， 生成 2-(2-Chlorophenyl)-5,7-dimethoxy-8-(piperidin-1-ylmethyl)chromen-4-one
  参考文献：
  名称：

  Nitrogen-containing flavonoids as CDK1/Cyclin B inhibitors: Design, synthesis, and biological evaluation

  摘要：

  A novel series of nitrogen-containing flavonoids 5a-1, 6a,b, and 7a,b were designed and synthesized as cyclin-dependent kinases (CDKs) inhibitors. The representative compounds 5a, 5b, 5e, and 5g showed potent CDK1/Cyclin B inhibitory activities. All compounds displayed a significant growth inhibitory action in vitro against Bel-7402, PC-3, ECA-109, A-549, HL-60, and MCF-7 cancer cell lines. Flow cytometry analysis showed that 5b induced apoptosis in PC-3 cells. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.07.088
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 (E)-3-(2-chlorophenyl)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Nitrogen-containing flavonoids as CDK1/Cyclin B inhibitors: Design, synthesis, and biological evaluation

  摘要：

  A novel series of nitrogen-containing flavonoids 5a-1, 6a,b, and 7a,b were designed and synthesized as cyclin-dependent kinases (CDKs) inhibitors. The representative compounds 5a, 5b, 5e, and 5g showed potent CDK1/Cyclin B inhibitory activities. All compounds displayed a significant growth inhibitory action in vitro against Bel-7402, PC-3, ECA-109, A-549, HL-60, and MCF-7 cancer cell lines. Flow cytometry analysis showed that 5b induced apoptosis in PC-3 cells. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.07.088

文献信息

• Design, Synthesis and Docking Studies of Flavokawain B Type Chalcones and Their Cytotoxic Effects on MCF-7 and MDA-MB-231 Cell Lines
  作者：Addila Abu Bakar、Muhammad Akhtar、Norlaily Mohd Ali、Swee Yeap、Ching Quah、Wan-Sin Loh、Noorjahan Alitheen、Seema Zareen、Zaheer Ul-Haq、Syed Shah

  DOI：10.3390/molecules23030616

  日期：——

  Flavokawain B (1) is a natural chalcone extracted from the roots of Piper methysticum, and has been proven to be a potential cytotoxic compound. Using the partial structure of flavokawain B (FKB), about 23 analogs have been synthesized. Among them, compounds 8, 13 and 23 were found in new FKB derivatives. All compounds were evaluated for their cytotoxic properties against two breast cancer cell lines

  Flavokawain B（1）是从Piper methysticum的根中提取的天然查尔酮，已被证明是潜在的细胞毒性化合物。使用黄酮类固醇B的部分结构（FKB），已经合成了约23个类似物。其中，在新的FKB衍生物中发现了化合物8、13和23。评估了所有化合物对两种乳腺癌细胞MCF-7和MDA-MB-231的细胞毒性，从而建立了结构-活性关系。FKB衍生物16（IC50 = 6.50±0.40和4.12±0.20μg/ mL），15（IC50 = 5.50±0.35和6.50±1.40μg/ mL）和13（IC50 = 7.12±0.80和4.04±0.30μg/ mL）对MCF-7和MDA-MB-231细胞系具有潜在的细胞毒性作用。但是，甲氧基在化合物2的第3位和第4位取代（IC50 = 8.90±0.60和6.80±0。35μg/ mL）和22（IC50 = 8.80±0.35和14.16±1
• Antifungal Activity and Studies on Mode of Action of Novel Xanthoxyline-Derived Chalcones
  作者：Paula Boeck、Paulo C. Leal、Rosendo A. Yunes、Valdir Cechinel Filho、Silvia López、Maximiliano Sortino、Andrea Escalante、Ricardo L. E. Furlán、Susana Zacchino

  DOI：10.1002/ardp.200400929

  日期：2005.3

  substituent on ring A are sufficient for these compounds to have antifungal properties. The chalcone 3‐(2‐chlorophenyl)‐1‐(2′‐hydroxy‐4′,6′‐dimethoxyphenyl)prop‐2‐en‐1‐one, with a Cl atom in the ortho position of benzene ring B showed the best antifungal activity against standardized strains of Trichophyton rubrum (MIC = 12.5 μg/mL) and inhibited all of the ten clinical isolates of T. rubrum tested (MIC at which

  查耳酮和查耳酮类化合物，其中大多数是新化合物，通过适当的醛和黄嘌呤的碱催化缩合制备，通过琼脂稀释法测试了对一组酵母、hialohyphomycetes 和皮肤癣菌的抗真菌特性。结果表明，仅存在“类黄酮素”取代模式或环 A 上的 2'-OH 取代都不足以使这些化合物具有抗真菌特性。查耳酮 3-(2-氯苯基)-1-(2'-羟基-4', 6'-二甲氧基苯基)丙-2-烯-1-1，在苯环B的邻位有一个Cl原子表明对红色毛癣菌标准化菌株 (MIC = 12.5 μg/mL) 具有最佳抗真菌活性，并抑制所有十种临床分离株。rubrum 测试（50% [MIC50] 和 90% [MIC90] 的分离株被抑制时的 MIC = 12.5 和 25 μg/mL）。关于其作用方式，粗糙脉孢菌试验显示该查耳酮产生的抑制晕圈出现斑点，强烈表明它可以通过抑制真菌细胞壁发挥作用。该查尔酮似乎是一种菌丝畸形诱导剂，因为在
• Efficient One‐Pot Synthesis of Hydroxyflavanones by Cyclization and<i>O</i>‐Demethylation of Methoxychalcones
  作者：Tao Liu、Huazhou Ying、Guan Lin、Yongzhou Hu

  DOI：10.1080/00397910801991465

  日期：2008.5

  An efficient one-pot method for the synthesis of hydroxyflavanones is described. Methoxychalcones are treated with 36% HBr to afford cyclization and regioselective O-demethylation products (2a-i) while cyclization and complete O-demethylation products (3a-e) are obtained in the presence of 45% HI.
• Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein
  作者：Kapil Juvale、Veronika F.S. Pape、Michael Wiese

  DOI：10.1016/j.bmc.2011.10.074

  日期：2012.1

  Breast cancer resistance protein (BCRP/ABCG2) belongs to the ATP binding cassette family of transport proteins. BCRP has been found to confer multidrug resistance in cancer cells. A strategy to overcome resistance due to BCRP overexpression is the investigation of potent and specific BCRP inhibitors. The aim of the current study was to investigate different multi-substituted chalcones for their BCRP inhibition. We synthesized chalcones and benzochalcones with different substituents (viz. OH, OCH3, Cl) on ring A and B of the chalcone structure. All synthesized compounds were tested by Hoechst 33342 accumulation assay to determine inhibitory activity in MCF-7 MX and MDCK cells expressing BCRP. The compounds were also screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity in the calcein AM accumulation assay and were found to be selective towards inhibition of BCRP. Substituents at position 20 and 40 on chalcone ring A were found to be essential for activity; additionally there was a great influence of substituents on ring B. Presence of 3,4-dimethoxy substitution on ring B was found to be optimal, while presence of 2- and 4-chloro substitution also showed a positive effect on BCRP inhibition. (C) 2011 Elsevier Ltd. All rights reserved.
• Antimitotic and Antiproliferative Activities of Chalcones: Forward Structure–Activity Relationship
  作者：Ahcène Boumendjel、Julien Boccard、Pierre-Alain Carrupt、Edwige Nicolle、Madeleine Blanc、Annabelle Geze、Luc Choisnard、Denis Wouessidjewe、Eva-Laure Matera、Charles Dumontet

  DOI：10.1021/jm0708331

  日期：2008.4.1

  A series of 59 chalcones was prepared and evaluated for the antimitotic effect against K562 leukemia cells. The most active chalcones were evaluated for their antiproliferative activity against a panel of I I human and murine cell cancer lines. We found that three chalcones were of great interest as potential antimitotic drugs. In vivo safety studies conducted on one of the most active chalcones revealed that the compound was safe, allowing further in vivo antitumor evaluation.