(E)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one

• 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-(3-nitrophenyl)prop-2-en-1-one
• 英文别名: 4',6'-Dimethoxy-2'-hydroxy-3-nitrochalcone；(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₅NO₆
• 分子量: 329.309
• InChiKey: RNJWVWDASBIOQQ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 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：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以62%的产率得到5,7-dimethoxy-3'-nitroflavone
  参考文献：
  名称：

  Efficient Synthesis of Nitroflavones by Cyclodehydrogenation of 2′-Hydroxychalcones and by the Baker-Venkataraman Method

  摘要：

  Several nitroflavone derivatives were synthesized by cyclodehydrogenation of 2'-hydroxychalcones and by the Baker-Venkataraman approach, starting from 2'-hydroxyacetophenones and benzoic acid derivatives. Nitroflavones synthesised by the first synthetic approach were obtained in better global yields than those obtained by the later method. The structures of all new compounds were elucidated by microanalyses, 1D and 2D NMR, IR, and mass spectroscopic measurements.

  DOI：

  10.1007/s00706-006-0550-9
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 间硝基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以57%的产率得到(E)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  新型黄嘌呤衍生查耳酮的抗真菌活性和作用方式研究

  摘要：

  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

  DOI：

  10.1002/ardp.200400929

文献信息

• [EN] NUCLEAR RECEPTOR MODULATORS AND THEIR USE FOR THE TREATMENT AND PREVENTION OF CANCER<br/>[FR] MODULATEURS DE RÉCEPTEURS NUCLÉAIRES ET LEUR UTILISATION POUR LE TRAITEMENT ET LA PRÉVENTION D'UN CANCER
  申请人：US HEALTH

  公开号：WO2012174436A1

  公开（公告）日：2012-12-20

  Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R1 to R5 and X1 to X5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.

  本文披露了一些化合物，它们是核受体调节剂，可以作为雄激素受体的拮抗剂，例如，公式I的化合物：其中R1至R5和X1至X5如本文所述，以及其药用盐、溶剂化合物和立体异构体。还披露了包括这些化合物的药物组合物，以及使用方法和治疗癌症，包括前列腺癌、其他核受体介导的癌症和其他疾病的方法。
• 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
• [EN] DRUG FOR ANTAGONIZING REPLICATION OF PORCINE REPRODUCTIVE AND RESPIRATORY SYNDROME VIRUS AND APPLICATION THEREOF<br/>[FR] MÉDICAMENT POUR ANTAGONISER LA RÉPLICATION DU VIRUS DU SYNDROME RESPIRATOIRE ET REPRODUCTEUR PORCIN ET SON APPLICATION<br/>[ZH] 一种拮抗猪繁殖与呼吸综合征病毒复制的药物及其应用
  申请人：UNIV NANJING AGRICULTURAL

  公开号：WO2021068533A1

  公开（公告）日：2021-04-15

  一种拮抗猪繁殖与呼吸综合征病毒复制的药物及其应用，采用病毒感染试验，从386种植物来源的天然药物库中首次发现一种PRRSV拮抗药物—黄腐酚。黄腐酚在Marc-145和PAM细胞上均可有效抑制PRRSV复制。人工合成5种不同分子结构的黄腐酚衍生物，发现衍生物Xn-4体外抑制病毒复制作用最强。仔猪人工感染和药物治疗试验结果显示，Xn-4能够有效地抑制PRRSV病毒血症，减轻感染猪临床症状，显著降低肺部炎症和病理损伤。
• Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA
  作者：Louise Domeneghini Chiaradia、Alessandra Mascarello、Marcela Purificação、Javier Vernal、Marlon Norberto Sechini Cordeiro、María Emilia Zenteno、Andréa Villarino、Ricardo José Nunes、Rosendo Augusto Yunes、Hernán Terenzi

  DOI：10.1016/j.bmcl.2008.09.105

  日期：2008.12

  In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were obtained by aldolic condensation between aldehydes and acetophenones, under basic conditions. Five compounds presented moderate or good activity. The structure - activity analysis reveals that the predominant factor for the activity is the molecule planarity/hydrophobicity and the nature of the substituents. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.