(E)-3-(3-hydroxy-4-methoxyphenyl)-1-phenylprop-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-(3-hydroxy-4-methoxyphenyl)-1-phenylprop-2-en-1-one
• 英文别名: (E)-3-Hydroxy-4-methoxychalcone
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: MSKJHPDSPSWNCA-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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)-3-(3-hydroxy-4-methoxyphenyl)-1-phenylprop-2-en-1-one 、 甘草次酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 [2-methoxy-5-[(E)-3-oxo-3-phenylprop-1-enyl]phenyl] (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
  参考文献：
  名称：

  Anti-tumor agents 255: Novel glycyrrhetinic acid–dehydrozingerone conjugates as cytotoxic agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.06.027
• 作为产物：
  描述：

  间苯二酚 在 sodium hydroxide 、 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 反应 5.33h， 生成 (E)-3-(3-hydroxy-4-methoxyphenyl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  一种查尔酮、二氢查尔酮和黄酮化合物的制备方法及应用

  摘要：

  本发明公开了一种查尔酮、二氢查尔酮和黄酮化合物的制备方法及应用，通过本发明合成方法合成的3,4’,6’‑三羟基‑4‑甲氧基查尔酮对a‑葡萄糖苷酶的抑制效果较强，可用于降低餐后高血糖；4‑二甲氨基查尔酮、4‑羟基查尔酮、3‑羟基‑4‑甲氧基查尔酮和3,4’,6’‑三羟基‑4‑甲氧基查尔酮对非酶糖基化的抑制效果均比较明显，可用于对糖尿病、动脉粥样硬化的治疗。

  公开号：

  CN108947858A

文献信息

• Study on the substituents' effects of a series of synthetic chalcones against the yeast Candida albicans
  作者：D. Batovska、St. Parushev、A. Slavova、V. Bankova、I. Tsvetkova、M. Ninova、H. Najdenski

  DOI：10.1016/j.ejmech.2006.08.012

  日期：2007.1

  A large series of chalcones were synthesized and studied for activity against Candida albicans. The SAR analysis showed that the antifungal activity was highly dependent on the substitution pattern of the aryl rings and correlated to a large extent with the ability of compounds to interact with sulfhydryl groups. The most active were the hydroxylated chalcones as their activity related to the location

  合成了大量查耳酮，并研究了其对白色念珠菌的活性。SAR分析表明，抗真菌活性高度依赖于芳基环的取代方式，并在很大程度上与化合物与巯基相互作用的能力有关。最具活性的是羟基化查耳酮，因为它们的活性与芳基环B中酚基的位置有关，如下所示：o-OH> p-OH约为3,4-di-OH> m-OH。获得的这些相关性和其他相关性极大地有助于设计抗候选查耳酮。
• Synthesis and biological evaluation of oleanolic acid derivative–chalcone conjugates as α-glucosidase inhibitors
  作者：Chu Tang、Linhui Zhu、Yu Chen、Rui Qin、ZhiNan Mei、Jing Xu、Guangzhong Yang

  DOI：10.1039/c3ra46492j

  日期：——

  α-Glucosidase is a promising target for the treatment of obesity and diabetes mellitus. A series of oleanolic acid derivative–chalcone conjugates were designed and synthesized as α-glucosidase inhibitors. Their structures were determined by spectroscopic analysis and their α-glucosidase inhibitory activities were investigated in vitro. Most conjugates exhibited moderate inhibitory activity against

  α-葡萄糖苷酶是治疗肥胖症和糖尿病的有希望的靶标。设计并合成了一系列齐墩果酸衍生物-查耳酮共轭物，作为α-葡萄糖苷酶抑制剂。通过光谱分析确定其结构，并在体外研究其对α-葡萄糖苷酶的抑制活性。大多数缀合物对α-葡萄糖苷酶表现出中等的抑制活性。其中，缀合物1b（IC 50= 3.2±0.2μM）具有最强的α-葡萄糖苷酶抑制活性，初步的构效关系表明，缀合物查尔酮单元中的呋喃环或噻吩环具有增强活性的趋势。Lineweaver-Burk图分析表明1b，6b，5c和4d竞争性抑制了α-葡萄糖苷酶的活性。它们的抑制常数（K i）分别为16.6、29.3、14.6和20.6μM。结合物和α-葡萄糖苷酶之间的相互作用力是氢键和范德华力。
• Curcuminoid Chalcones: Synthesis, Stability, and New Neuroprotective and Sonosensitising Activities
  作者：Dorota Olender、Małgorzata Józkowiak、Hanna Piotrowska-Kempisty、Katarzyna Sowa-Kasprzak、Lucjusz Zaprutko、Izabela Muszalska-Kolos、Ewa Baranowska-Wójcik、Dominik Szwajgier

  DOI：10.3390/ph16091331

  日期：——

  anti-inflammatory, antioxidant, and anticholinergic properties of some curcuminoid chalcones and curcuminoid chalcones hybrids were evaluated. The curcuminoid chalcone derivatives showed promising neuroprotective activity as sonosensitisers for sonodynamic therapy in the studied cell lines. Additionally, the stability of the ester-type hybrid compounds with promising activity was determined. The RP-HPLC method

  这项工作的主要目的是设计并获得一系列姜黄素查耳酮-NSAID 混合衍生物。布洛芬 (i)、酮洛芬 (ii) 和萘普生 (iii) 的酯型杂化化合物通过两种方式获得，即使用 Claisen-Schmidt 反应和 Steglich 酯化反应。设计的分子已成功合成，FT-IR、MS 和 NMR 光谱证实了其结构。此外，还评估了声动力疗法的细胞毒性作用以及一些类姜黄素查耳酮和类姜黄素查耳酮混合物的抗炎、抗氧化和抗胆碱能特性。类姜黄素查尔酮衍生物作为声敏剂在所研究的细胞系中显示出有希望的神经保护活性，用于声动力疗法。此外，还确定了具有良好活性的酯型杂化化合物的稳定性。采用RP-HPLC法观察受试化合物的降解情况。研究表明，酯型杂化化合物（3ai、3bi）的结构异构体具有相似的对降解因素的敏感性，即在碱性环境中极不稳定，在酸性环境中极不稳定，在中性环境中不稳定，实际上稳定在氧化环境中，在溶液和固相中对光不稳定。这些化合物在
• 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.
• Synthesis and anticancer activity of chalcones derived from vanillin and isovanillin
  作者：Saiharish Raghavan、Prasath Manogaran、Balasubramanian Kalpattu Kuppuswami、Ganesh Venkatraman、Krishna Kumari Gadepalli Narasimha

  DOI：10.1007/s00044-015-1453-2

  日期：2015.12

  An array of chalcones from vanillin/isovanillin and differently substituted acetophenones were synthesized and assessed for their anticancer activity against A549, MCF7 and MIA PaCa-2 cell lines using MTT assay. Some of the chalcones exhibited good anticancer activity with IC50 values below 10 mu M. Compound 5f with IC50 values 5.4 +/- A 0.7, 10.45 +/- A 2.15 and 13.0 +/- A 1.68 A mu M on MIA PaCa-2, A549 and MCF7, respectively, was more potent than curcumin and hence was analyzed for changes in cell morphology, inhibition of cell migration, mechanism of cell death and arrest of cell cycle progression on MIA PaCa-2 cells.