(E)-4-(3-ethoxy-4-hydroxyphenyl)but-3-en-2-one | 22292-71-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-(3-ethoxy-4-hydroxyphenyl)but-3-en-2-one
• CAS: 22292-71-3
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: IOXQYXKPHHHUIG-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (E)-4-(3-ethoxy-4-hydroxyphenyl)but-3-en-2-one 在 palladium 10% on activated carbon 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 6.0h， 生成 1-(3-ethoxy-4-hydroxyphenyl)-5-hydroxyoctan-3-one
  参考文献：
  名称：

  针对铜绿假单胞菌感染的纯RhlR拮抗剂的发现和表征。

  摘要：

  铜绿假单胞菌（P.aeruginosa）是一种机会性人类病原体，可形成生物膜并通过群体感应（QS）产生毒力因子。阻断铜绿假单胞菌的QS系统是减少生物膜形成和产生毒力因子的极好策略。RhlR在铜绿假单胞菌的QS系统中发挥重要作用。我们基于4-gingerol的化学结构合成了55个类似物，并使用基于细胞的报告基因菌株测定法评估了它们的RhlR抑制活性。全面的结构-活性关系研究确定了炔基酮30作为最有效的RhlR拮抗剂。该化合物对LasR和PqsR表现出选择性的RhlR拮抗作用，对生物膜的形成有很强的抑制作用，并减少了铜绿假单胞菌中毒力因子的产生。此外，用30只体内处理的黄粉虫幼虫的存活率大大提高。因此，化合物30，一种纯的RhlR拮抗剂，可以用于开发铜绿假单胞菌感染的QS调节分子。

  DOI：

  10.1021/acs.jmedchem.0c00630
• 作为产物：
  描述：

  乙基香兰素 在 sodium hydroxide 、 丙酮 作用下， 生成 (E)-4-(3-ethoxy-4-hydroxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  Berlin; Scherlin; Serebrennikowa, Zhurnal Obshchei Khimii, 1949, vol. 19, p. 759,763

  摘要：

  DOI：

文献信息

• Arylamine Ketones, Their Preparation Methods, The Pharmaceutical Composition Containing Them And Their Use
  申请人：Zhu Liya

  公开号：US20080221106A1

  公开（公告）日：2008-09-11

  Disclosed Arylamine ketones of formula (I), their preparation methods, the pharmaceutical compositions containing them and their use in preventing and/or treating the diseases related to the plaque-activating factors, especially in anti-inflammation and immunization, more especially in the treatment of the acute or chronic inflammation, such as, osteoarthritis, oarthritis deformans, etc.

  公开了式（I）的芳基胺酮化合物，它们的制备方法，含有它们的药物组合物以及在预防和/或治疗与斑块活化因子有关的疾病中的应用，特别是在抗炎和免疫方面，更特别地用于治疗急性或慢性炎症，如骨关节炎，变形性骨关节炎等。
• COMPOSITION FOR PREVENTING OR TREATING BACTERIAL INFECTIOUS DISEASE COMPRISING 4-GINGEROL DERIVATIVE COMPOUND AS ACTIVE INGREDIENT
  申请人：KOREA UNIVERSITY RESEARCH AND BUSINESS FOUNDATION, SEJONG CAMPUS

  公开号：US20220289657A1

  公开（公告）日：2022-09-15

  The present invention relates to a 4-gingerol derivative compound, or a racemate, isomer, or pharmaceutically acceptable salt thereof, the compound being capable of inhibiting biofilm formation and production of virulence factors. The 4-gingerol derivative compound according to the present invention has binding affinity to RhlR and corresponding RhlR antagonism activity that are significantly improved, and therefore can effectively inhibit biofilm formation and production of virulence factors. Furthermore, various bacterial infectious diseases caused by biofilms can be fundamentally prevented or treated by using a pharmaceutical composition comprising the 4-gingerol derivative compound, or a racemate, isomer, or pharmaceutically acceptable salt thereof as an active ingredient.

  本发明涉及4-姜醇衍生物化合物，或其外消旋体、异构体或药学上可接受的盐，该化合物能够抑制生物膜形成和致病因子的产生。本发明的4-姜醇衍生物化合物具有与RhlR的结合亲和力和相应的RhlR拮抗活性显著改善，因此可以有效地抑制生物膜形成和致病因子的产生。此外，通过使用包含4-姜醇衍生物化合物、其外消旋体、异构体或药学上可接受的盐作为活性成分的药物组合物，可以从根本上预防或治疗由生物膜引起的各种细菌感染性疾病。
• ARYLAMINE KETONES, THEIR PREPARATION METHODS, THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USE
  申请人：INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：EP1783115B1

  公开（公告）日：2016-07-13
• Dehydrozingerone, Chalcone, and Isoeugenol Analogues as in Vitro Anticancer Agents
  作者：Jin Tatsuzaki、Kenneth F. Bastow、Kyoko Nakagawa-Goto、Seiko Nakamura、Hideji Itokawa、Kuo-Hsiung Lee

  DOI：10.1021/np060252z

  日期：2006.10.1

  Twenty-eight compounds related to dehydrozingerone ( 1), isoeugenol ( 3), and 2-hydroxychalcone ( 4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogues 27-35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR ( a multidrug-resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC50 value of 0.6 mu g/mL. Furthermore, dehydrozingerone analogue 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC50 values of 2.0, 1.0, and 2.0 mu g/mL, respectively) and KB-VCR (IC50 values of 1.9, 1.0, and 2.0 mu g/mL, respectively) cells, suggesting that they are not substrates for the P-glycoprotein drug efflux pump.
• Anti-tumor agents 255: Novel glycyrrhetinic acid–dehydrozingerone conjugates as cytotoxic agents
  作者：Jin Tatsuzaki、Masahiko Taniguchi、Kenneth F. Bastow、Kyoko Nakagawa-Goto、Susan L. Morris-Natschke、Hideji Itokawa、Kimiye Baba、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2007.06.027

  日期：2007.9

  Esterification of glycyrrhetinic acid (GA) with dehydrozingerone (DZ) resulted in a novel cytotoxic GA-DZ conjugate. Based on this exciting finding, we conjugated eleven different DZ analogs with GA or other triterpenoids, including oleanoic acid (OA) or Ursolic acid UA). In an in vitro anti-cancer assay using nine different human tumor cell lines, most of the GA-DZ conjugates showed significant potency. Particularly, compounds 5, 29, and 30 showed significant cytotoxic effects against LN-Cap, 1 A9, and KB cells with ED50 values of 0.6, 0.8, and 0.9 mu M, respectively. Similar conjugates between DZ and OA or UA were inactive suggesting that the GA component is critical for activity. Notably, although GA-DZ conjugates showed potent cytotoxic activity, the individual components (GA and DZ analogs) were inactive. Thus, GA-DZ conjugates are new chemical entities and represent interesting hits for anti-cancer drug discovery and development. (c) 2007 Elsevier Ltd. All rights reserved.