(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one | 861107-94-0

• 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)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one
• 英文别名: (E)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(p-tolyl)prop-2-en-1-one；(E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-p-tolylprop-2-en-1-one；(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one；2'-hydroxy-4',6'-dimethoxy-4-methylchalcone；2'-hydroxy-4-methyl-4',6'-dimethoxychalcone；4',6'-Dimethoxy-2'-hydroxy-4-methylchalcone
• CAS: 861107-94-0
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: PWVBSDQARMAGHJ-CMDGGOBGSA-N

物化性质

• 熔点：
  61-63 °C(Solv: hexane (110-54-3); acetone (67-64-1))
• 沸点：
  511.6±50.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以63%的产率得到5-Hydroxy-7-methoxy-2-(4-methylphenyl)-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  Efficient One‐Pot Synthesis of Hydroxyflavanones by Cyclization andO‐Demethylation of Methoxychalcones

  摘要：

  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.

  DOI：

  10.1080/00397910801991465
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.5h， 生成 (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one
  参考文献：
  名称：

  新型的一氧化氮（NO）产生抑制剂的开发对慢性炎症具有潜在的治疗作用

  摘要：

  炎症是对刺激的复杂生物学反应。活化的巨噬细胞诱导过度释放促炎性细胞因子，而内源性自由基一氧化氮（NO）等介体在多种炎性疾病的进展中起重要作用。天然和合成查耳酮都具有广泛的生物活性。在这项工作中，基于生物活性卡瓦尔查耳酮，设计，合成了39个查耳酮和3种相关化合物，包括几种新化合物，并评估了它们对RAW 264.7细胞中NO产生的抑制作用。新型化合物（E）-1-（2'-羟基-4'，6'-二甲氧基苯基）-3-（3-甲氧基-4-（3-吗啉代丙氧基）苯基）丙-2-烯-1-酮（53）对10μM（IC的NO产生）表现出更好的抑制活性（84.0％）50  = 6.4μM）的细胞毒性（IC 50  > 80μM）在测试化合物中最低。此外，蛋白质印迹分析表明化合物53是诱导型一氧化氮合酶（iNOS）蛋白的有效下调剂。对接研究表明，化合物53也可以对接iNOS的活性位点。此外，在剂量为10 mg / kg /

  DOI：

  10.1016/j.ejmech.2020.112216

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS COMPRISING CDK INHIBITORS AND METHODS FOR THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS ET COMPOSITIONS COMPRENANT DES INHIBITEURS DES CDK ET MÉTHODES DE TRAITEMENT DU CANCER
  申请人：UNIV GEORGIA STATE RES FOUND

  公开号：WO2010129858A1

  公开（公告）日：2010-11-11

  Disclosed herein are compounds suitable for use as antitumor agents, methods for treating cancer wherein the disclosed compounds are used in making a medicament for the treatment of cancer, methods for treating a tumor comprising, administering to a subject a composition comprising one or more of the disclosed cytotoxic agents, and methods for preparing the disclosed antitumor agents.

  本文披露了适用作抗肿瘤药剂的化合物，用于治疗癌症的方法，其中所披露的化合物用于制备治疗癌症的药物，治疗肿瘤的方法包括向受试者施用包含一种或多种所披露的细胞毒性药剂的组合物，以及制备所披露的抗肿瘤药剂的方法。
• 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
• COMPOUNDS AND COMPOSITIONS COMPRISING CDK INHIBITORS AND METHODS FOR TREATING CANCER
  申请人：Xu Wen Fang

  公开号：US20120121692A1

  公开（公告）日：2012-05-17

  Disclosed herein are compounds suitable for use as antitumor agents, methods for treating cancer wherein the disclosed compounds are used in making a medicament for the treatment of cancer, methods for treating a tumor comprising, administering to a subject a composition comprising one or more of the disclosed cytotoxic agents, and methods for preparing the disclosed antitumor agents.

  本文披露了适用于作为抗肿瘤剂的化合物，其中所披露的化合物用于制备用于治疗癌症的药物，治疗肿瘤的方法包括向受试者投与含有所披露的细胞毒性药物之一或多个的组合物，以及制备所披露的抗肿瘤剂的方法。
• Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity
  作者：Anastasia Detsi、Maya Majdalani、Christos A. Kontogiorgis、Dimitra Hadjipavlou-Litina、Panagiotis Kefalas

  DOI：10.1016/j.bmc.2009.10.002

  日期：2009.12

  A series of 2'-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of chalcone analogues with increased antileishmanial activity
  作者：Paula Boeck、Camila Alves Bandeira Falcão、Paulo César Leal、Rosendo Augusto Yunes、Valdir Cechinel Filho、Eduardo Caio Torres-Santos、Bartira Rossi-Bergmann

  DOI：10.1016/j.bmc.2005.10.005

  日期：2006.3

  Eighteen analogues of an active natural chalcone were synthesized using xanhoxyline and some derivatives, and these analogues were tested for selective activity against both promastigotes and intracellular amastigotes of Leishmania amazonensis in vitro. Three analogues (10, 12, and 19) containing nitro, fluorine or bromine groups, respectively, displayed increased selective activity against the parasites as compared with the natural chalcone. The nitrosylated chalcone 10 was also tested intralesionally in infected mice and was found to be as effective as Pentostan reference drug at a dose 100 times higher than that of the chalcone in controlling both the lesion growth and the parasite burden. (c) 2005 Elsevier Ltd. All rights reserved.