(E)-3-(4-(dimethylamino)phenyl)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)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)-3-(4-(dimethylamino)phenyl)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxy-4, 6-dimethoxyphenyl)prop-2-en-1-one；(E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one；4-(dimethylamino)-2'-hydroxy-4',6'-dimethoxychalcone；4',6'-Dimethoxy-4-dimethylamino-2'-hydroxychalcone；(E)-3-[4-(dimethylamino)phenyl]-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: AJBXYCXQFLOEKN-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-(dimethylamino)phenyl)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)prop-2-en-1-one 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以75%的产率得到2-[4-(Dimethylamino)phenyl]-5-hydroxy-7-methoxy-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-羟基-4,6-二甲氧基苯乙酮 、 对二甲氨基苯甲醛 以 乙醇 、 水 为溶剂， 生成 (E)-3-(4-(dimethylamino)phenyl)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Flavokawain B型Chalcones的设计，合成和对接研究及其对MCF-7和MDA-MB-231细胞系的细胞毒性作用。

  摘要：

  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

  DOI：

  10.3390/molecules23030616

文献信息

• Mechanisms of action and structure-activity relationships of cytotoxic flavokawain derivatives
  作者：Charlotte Thieury、Nicolas Lebouvier、Rémy Le Guével、Yann Barguil、Gaëtan Herbette、Cyril Antheaume、Edouard Hnawia、Yoshinori Asakawa、Mohammed Nour、Thierry Guillaudeux

  DOI：10.1016/j.bmc.2017.01.049

  日期：2017.3

  22 Flavokawain derivatives (FKd) were obtained by one step syntheses in order to conduct a SAR study to understand the structural requirements for optimum and selective cytotoxicity. FKd and natural flavokawains A and B found into kava, a South Pacific traditional beverage, were evaluated against nine cancer and one healthy cell lines. The targeted cell cycle phases as well as the effects on the induction of apoptosis and cell cycle protein levels were investigated. Therapeutic improvements (more activity and selectivity) were achieved with FKd compared to natural flavokawains and notably with the 2',3,4',6'-tetramethoxychalcone (FKd 19). FKd induced a Gl/S arrest on p53 wild-type cells and an M arrest on p53 mutant-type, via the up-regulation of p21 and cyclin B1 proteins, followed by apoptosis. Moreover, FKd exhibited a 24 h-effect on Akt/mTor normal cells versus a 48 h-effect on Akt/mTor up-regulated cells. The SAR study resulted in the conclusion that trimethoxy A-ring allowed the best compromise between cytotoxicity and selectivity, as well as the substitution of the meta position on the B-ring and the use of halogens substituents. (C) 2017 Elsevier Ltd. All rights reserved.
• Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure–activity relationship analysis and regulation of apoptotic proteins
  作者：Chun Wai Mai、Marzieh Yaeghoobi、Noorsaadah Abd-Rahman、Yew Beng Kang、Mallikarjuna Rao Pichika

  DOI：10.1016/j.ejmech.2014.03.002

  日期：2014.4

  In the present study, a series of 46 chalcones were synthesised and evaluated for antiproliferative activities against the human TRAIL-resistant breast (MCF-7, MDA-MB-231), cervical (HeLa), ovarian (Caov-3), lung (A549), liver (HepG2), colorectal (HT-29), nasopharyngeal (CNE-1), erythromyeloblastoid (K-562) and T-Iymphoblastoid (CEM-SS) cancer cells. The chalcone 38 containing an amino (-NH2) group on ring A was the most potent and selective against cancer cells. The effects of the chalcone 38 on regulation of 43 apoptosis-related markers in HT-29 cells were determined. The results showed that 20 apoptotic markers (Bad, Bax, BcI-2, Bcl-w, Bid, Bim, CD40, Fas, HSP27, IGF-1, IGFBP-4, IGFBP-5, Livin, p21, Survivin, 5TNE-R2, TRAIL-R2, XIAP, caspase-3 and caspase-8) were either up regulated or down regulated. (C) 2014 Elsevier Masson SAS.All rights reserved.
• Design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship
  作者：Muhammad Nadeem Akhtar、Nurshafika M. Sakeh、Seema Zareen、Sana Gul、Kong Mun Lo、Zaheer Ul-Haq、Syed Adnan Ali Shah、Syahida Ahmad

  DOI：10.1016/j.molstruc.2014.12.073

  日期：2015.4

  Browning of fruits and vegetables is a serious issue in the food industry, as it damages the organoleptic properties of the final products. Overproduction of melanin causes aesthetic problems such as melisma, freckles and lentigo. In this study, a series of chalcones (1-10) have been synthesized and examined for their tryrosinase inhibitory activity. The results showed that flavokawain B (1), flavokawain A (2) and compound 3 were found to be potential tyrosinase inhibitors, indicating IC50 14.20-14.38 mu M values. This demonstrates that 4-substituted phenolic compound especially at ring A exhibited significant tyrosinase inhibition. Additionally, molecular docking results showed a strong binding affinity for compounds 1-3 through chelation between copper metal and ligands. The detailed molecular docking and SARs studies correlate well with the tyrosinase inhibition studies in vitro. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and single X-ray crystallographic techniques. These findings could lead to design and discover of new tyrosinase inhibitors to control the melanine overproduction and overcome the economic loss of food industry. (C) 2014 Elsevier B.V. All rights reserved.
• US4605674A
  申请人：——

  公开号：US4605674A

  公开（公告）日：1986-08-12
• [EN] ESTROGEN RECEPTOR ALPHA COLIGANDS, AND METHODS OF USE THEREOF<br/>[FR] CO-LIGANDS DES RÉCEPTEURS DES OESTROGÈNES ALPHA ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV CALIFORNIA

  公开号：WO2017132135A1

  公开（公告）日：2017-08-03

  Provided herein is a coligand for the estrogen receptor (ER) α subunit, and methods of use thereof in treating conditions associated with ER signaling in an individual. The present ERα coligand may be a cell type-selective, allosteric modulator of ERα signaling. The ERα coligand, when administered to an individual, may modulate ER agonist-dependent signaling in a tissue-selective manner.