4'-hydroxy-3'-methoxychalcone | 854835-26-0

• 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: 4'-hydroxy-3'-methoxychalcone
• 英文别名: 1-(4-hydroxy-3-methoxyphenyl)-3-phenyl-2-propen-1-one；3'-Methoxy-4'-hydroxychalcone；1-(4-hydroxy-3-methoxyphenyl)-3-phenylprop-2-en-1-one
• CAS: 854835-26-0
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: SBOLHVAMAJVIIF-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195 °C
• 沸点：
  454.4±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：

  4'-hydroxy-3'-methoxychalcone 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以72%的产率得到2-methoxy-4-(5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)phenol
  参考文献：
  名称：

  新型吡唑啉类似物的单胺氧化酶抑制活性：姜黄素的设计与合成

  摘要：

  一系列新的2-甲氧基-4-（5-苯基-4,5-二氢-1- ħ吡唑-3-基）phenolderivatives，4 - 13，合成以及它们的人MAO抑制活性进行测试。发现除了hMAO-B的选择性抑制剂4和非选择性抑制剂12以外，所有化合物均对hMAO-A具有选择性和可逆性。发现化合物7是hMAO-A的有效抑制剂，K i = 0.06± 0.003μM ，选择性指数为（SI = 1.02×10 –5）。已发现它比标准药物莫氯贝胺（hMAO-A，K i =0.11±0.01μM），选择性指数SI = 0.049。进行分子对接模拟以了解负责选择性和效能的关键相互作用。

  DOI：

  10.1021/acsmedchemlett.5b00326
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4'-hydroxy-3'-methoxychalcone
  参考文献：
  名称：

  新型吡唑啉类似物的单胺氧化酶抑制活性：姜黄素的设计与合成

  摘要：

  一系列新的2-甲氧基-4-（5-苯基-4,5-二氢-1- ħ吡唑-3-基）phenolderivatives，4 - 13，合成以及它们的人MAO抑制活性进行测试。发现除了hMAO-B的选择性抑制剂4和非选择性抑制剂12以外，所有化合物均对hMAO-A具有选择性和可逆性。发现化合物7是hMAO-A的有效抑制剂，K i = 0.06± 0.003μM ，选择性指数为（SI = 1.02×10 –5）。已发现它比标准药物莫氯贝胺（hMAO-A，K i =0.11±0.01μM），选择性指数SI = 0.049。进行分子对接模拟以了解负责选择性和效能的关键相互作用。

  DOI：

  10.1021/acsmedchemlett.5b00326

文献信息

• Selective Synthesis of 3,4-Dihydrocoumarins and Chalcones from Substituted Aryl Cinnamic Esters
  作者：Jae-Ho Jeon、Deok-Mo Yang、Jong-Gab Jun

  DOI：10.5012/bkcs.2011.32.1.65

  日期：2011.1.20

  Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by $TiCl_4$. This method can be used for preparing various coumarin & chalcone compounds.

  香豆素广泛存在于植物王国中，并已被用作抗癌剂、抗真菌剂、抗凝血剂和杀虫剂。查尔酮也在植物王国中广泛分布，并且已知具有多种生物活性，包括抗菌、抗真菌、抗癌和抗炎等。由于它们被认为是重要的天然产物，迄今为止已经报道了许多合成方法。我们设计了一种新的选择性方法，通过选择试剂，从芳基肉桂酸制备二氢香豆素和查尔酮。通过使用对甲苯磺酸催化的分子内环化反应，选择性地制备了二氢香豆素衍生物。此外，还通过三氯化钛催化的Fries重排反应制备了查尔酮。这种方法可以用于制备各种香豆素和查尔酮化合物。
• Discovery of CAPE derivatives as dual EGFR and CSK inhibitors with anticancer activity in a murine model of hepatocellular carcinoma
  作者：Xiaoyu Liu、Qianqian Du、Caiping Tian、Mei Tang、Yingjun Jiang、Yong Wang、Yang Cao、Zhe Wang、Zhenwei Wang、Jing Yang、Yan Li、Xiaozhen Jiao、Ping Xie

  DOI：10.1016/j.bioorg.2020.104536

  日期：2021.2

  Thiol Reactivity Profiling), epidermal growth factor receptor (EGFR) and C-terminal Src kinase (CSK) were supposed to the targets of 8f, which was confirmed by binding mode analysis. Furthermore, compounds 8f, 8l, 8j, 8k, 8g, and 8h showed potent inhibitory effects against both CSK and EGFR than other derivatives in an ADP-Glo™ kinase assay. The representative compound, 8f, potently inhibited various

  咖啡酸苯乙酯（CAPE）是一种从蜂巢蜂胶中提取的生物活性成分，可以抑制肝细胞癌（HCC）。为了探索更稳定的 CAPE 衍生物，设计、合成了 25 种化合物，并进行了体外和体内药理学评估，作为 HCC 的抗肿瘤剂。化合物8d、8f、8l、8j和8k在HCC细胞系中显示出比包括CAPE在内的其他化合物有利的抗增殖活性。根据QTRP（Quantitative Thiol Reactivity Profiling）的结果，表皮生长因子受体（EGFR）和C端Src激酶（CSK）被认为是8f的靶标，这通过结合模式分析得到证实。此外，在 ADP-Glo​​™ 激酶测定中，化合物8f、8l、8j、8k、8g和8h对 CSK 和 EGFR 均显示出强于其他衍生物的抑制作用。代表性化合物8f有效抑制小鼠模型中的各种肿瘤生长，包括小鼠肝细胞癌 H22，同时下调 EGFR/AKT 通路并通过抑制 CSK 增强 T
• Inhibitory effects of chalcone glycosides isolated from Brassica rapa L. ‘hidabeni’ and their synthetic derivatives on LPS-induced NO production in microglia
  作者：Hirokazu Hara、Yoko Nakamura、Masayuki Ninomiya、Ryosuke Mochizuki、Tetsuro Kamiya、Elias Aizenman、Mamoru Koketsu、Tetsuo Adachi

  DOI：10.1016/j.bmc.2011.07.036

  日期：2011.9

  Activation of microglia induces the production of various inflammatory mediators including nitric oxide (NO), leading to neurodegeneration in many central nervous system diseases. In this study, we examined the effects of chalcone glycosides isolated from Brassica rapa L. ‘hidabeni’ on lipopolysaccharide (LPS)-induced NO production using rat immortalized microglia HAPI cells. 4′-O-β-d-Glucopyranosyl-3′

  小胶质细胞的激活诱导各种炎症介质的产生，包括一氧化氮（NO），导致许多中枢神经系统疾病的神经变性。在这项研究中，我们研究了使用永生化的小胶质细胞HAPI细胞从芸苔属'hidabeni'分离的查尔酮苷对脂多糖（LPS）诱导的NO产生的影响。4'- ø -β- d吡喃葡萄糖基-3'，4-dimethoxychalcone（A2）抑制LPS诱导的可诱导的一氧化氮合酶（iNOS）的表达和NO生产。但是，A2不会影响核因子-κB和有丝分裂原激活的蛋白激酶途径。信号转导和转录激活因子1（STAT1）通过LPS产生IFN-β激活，是负责LPS诱导的iNOS表达的重要转录因子。A2抑制LPS诱导的STAT1的磷酸化和核易位，尽管它对LPS诱导的IFN-β表达没有影响。这些结果表明，A2的抑制作用归因于STAT信号转导的预防。此外，对新合成的“ hidabeni”查尔酮衍生物的构效关系研究表明，4' - O
• Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
  作者：Lorraine M. Deck、Lucy A. Hunsaker、Thomas A. Vander Jagt、Lisa J. Whalen、Robert E. Royer、David L. Vander Jagt

  DOI：10.1016/j.ejmech.2017.11.048

  日期：2018.1

  Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability, to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues. (C) 2017 Published by Elsevier Masson SAS.
• Curcumin-cinnamaldehyde hybrids as antiproliferative agents against women’s cancer cells
  作者：Daiane B. Anselmo、Carlos R. Polaquini、Beatriz C. Marques、Gabriela M. Ayusso、Letícia R. Assis、Guilherme S. Torrezan、Paula Rahal、Ana L. Fachin、Marília F. Calmon、Mozart A. Marins、Luis O. Regasini

  DOI：10.1007/s00044-021-02783-w

  日期：——