1-(2-Hydroxyphenyl)-3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-en-1-one | 4537-34-2

• 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: 1-(2-Hydroxyphenyl)-3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(2-hydroxyphenyl)-3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 4537-34-2
• 化学式: C₂₃H₂₀O₄
• 分子量: 360.409
• InChiKey: GOFLNFZOOOWWAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-Hydroxyphenyl)-3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-en-1-one 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 96.0h， 以77%的产率得到4'-hydroxy-3'-methoxy-5'-benzylflavanone
  参考文献：
  名称：

  （苄氧基）查耳酮的酸性重排：Chamanetin的简短合成。

  摘要：

  在回流的氯仿中用三氟乙酸处理（苄氧基）查耳酮以高收率和良好的区域选择性得到了几种新的苄基（羟基）黄酮。通过使用此程序，我们从容易获得的试剂中以高收率制备了天然化合物Chamanetin。 苄基化-重排-保护基-香豆素-查尔酮

  DOI：

  10.1055/s-0029-1217064
• 作为产物：
  描述：

  氯化苄 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 30.25h， 生成 1-(2-Hydroxyphenyl)-3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  （苄氧基）查耳酮的酸性重排：Chamanetin的简短合成。

  摘要：

  在回流的氯仿中用三氟乙酸处理（苄氧基）查耳酮以高收率和良好的区域选择性得到了几种新的苄基（羟基）黄酮。通过使用此程序，我们从容易获得的试剂中以高收率制备了天然化合物Chamanetin。 苄基化-重排-保护基-香豆素-查尔酮

  DOI：

  10.1055/s-0029-1217064

文献信息

• Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin
  作者：Junxiu Meng、Tao Jiang、Huma Aslam Bhatti、Bina S. Siddiqui、Sally Dixon、Jeremy D. Kilburn

  DOI：10.1039/b918179b

  日期：——

  Structural revision of lawsonicin, a natural product of Lawsonia alba, is reported based upon comparison of its spectral data with that of the naturally occurring dihydrobenzo[b]furan neolignan (rac)-trans-dihydrodehydrodiconiferyl alcohol, which is found to be identical. A concise synthesis of dihydrodehydrodiconiferyl alcohol, via Rh2[S-DOSP]4-catalysed intramolecular C–H insertion, is described.

  根据与天然存在的二氢苯并[b]呋喃新木质素（rac）-反式-二氢去氢二苯醇的光谱数据比较，报道了天芥菜（Lawsonia alba）天然产物lawsonicin的结构修订。还描述了通过Rh2[S-DOSP]4催化的分子内C-H插入反应合成二氢去氢二苯醇的简洁合成方法。
• An efficient oxidative conversion of 2-aryl-2H-chromenes to the corresponding flavones by tert-butylhydroperoxide and copper bromide
  作者：Dipanwita Banerjee、Utpal Kayal、Gourhari Maiti

  DOI：10.1016/j.tetlet.2016.03.006

  日期：2016.4

  A simple and efficient method has been developed for the facile oxidation of chromenes to the corresponding flavones by tert-butylhydroperoxide (TBHP) in the presence of copper(II) bromide catalyst in toluene at 80 °C in a very short time. The reaction demonstrates excellent reactivity, functional group tolerance, and good to excellent yields without using conventional strong oxidizing agents.

  已经开发了一种简单有效的方法，用于在80℃下于很短时间内在甲苯中存在溴化铜（II）的情况下，通过叔丁基氢过氧化物（TBHP）轻松地将二甲基苯酮氧化为相应的黄酮。该反应显示出优异的反应性，官能团耐受性以及良好至优异的产率，而无需使用常规的强氧化剂。
• Synthesis and biological evaluation of substituted aurone derivatives as potential tyrosinase inhibitors: <i>in vitro</i>, kinetic, QSAR, docking and drug-likeness studies
  作者：Najla A. Alshaye、Ehsan Ullah Mughal、Eslam B. Elkaeed、Zaman Ashraf、Sana Kehili、Yasir Nazir、Nafeesa Naeem、Nida Abdul Majeed、Amina Sadiq

  DOI：10.1080/07391102.2022.2132296

  日期：——

  synthesized aurone derivatives were found as potent tyrosinase inhibitors relative to the standard kojic acid (IC50 = 16.69 ± 2.81 μM) and the compound 39 inhibited tyrosinase non-competitively (Ki = 11.8 μM) by forming an enzyme-inhibitor complex. The binding modes of these molecules were ascribed through molecular docking studies against tyrosinase protein (PDB ID: 2Y9X). The quantitative structure-activity

  摘要 酪氨酸酶在黑色素生物合成和水果和蔬菜的酶促褐变中起着重要作用。为了发现有效的酪氨酸酶抑制剂，进行了本研究。在此背景下，通过各种光谱技术（包括红外、紫外、 1 H 和13 C-NMR 以及质谱）设计、合成并阐明了合成傲酮衍生物26-50的结构。筛选了目标化合物26-50的抗酪氨酸酶抑制潜力，并通过Lineweaver-Burk图分析了动力学机制。所有目标化合物均表现出良好至优异的 IC 50值，范围为 7.12 ± 0.32 μM 至 66.82 ± 2.44 μM。这些合成的橙酮衍生物被发现是相对于标准曲酸的有效酪氨酸酶抑制剂（IC 50 = 16.69 ± 2.81 μM），并且化合物39通过形成酶抑制剂复合物非竞争性抑制酪氨酸酶（K i = 11.8 μM）。这些分子的结合模式是通过针对酪氨酸酶蛋白（PDB ID：2Y9X）的分子对接研究来确定的。定量构效关系研究显示26-50个结构与其抗酪氨酸酶活性(IC
• 3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells
  作者：Francisco Estévez-Sarmiento、Mercedes Said、Ignacio Brouard、Francisco León、Celina García、José Quintana、Francisco Estévez

  DOI：10.1016/j.bmc.2017.09.043

  日期：2017.11

  Flavonoids are naturally occurring polyphenolic compounds and are among the most promising anticancer agents. A series of flavonols and their 3-methyl ether derivatives were synthesized and assessed for cytotoxicity. It was found that 3'-hydroxy-3,4'-dimethoxyflavone (flavonoid 7a) displayed strong cytotoxicity against human SK-MEL-1 melanoma cells and blocked tubulin polymerization, but had no significant cytotoxic effects against quiescent or proliferating human peripheral blood mononuclear cells. Our analyses showed that flavonoid 7a induces G2-M cell cycle arrest and apoptosis in melanoma cells which is associated with cytochrome c release and activation of both extrinsic and intrinsic apoptotic pathways of cell death. (C) 2017 Elsevier Ltd. All rights reserved.
• Exploration of Pharmacophore in Chrysosplenol C as Activator in Ventricular Myocyte Contraction
  作者：Eeda Venkateswararao、Min-Jeong Son、Niti Sharma、Manoj Manickam、PullaReddy Boggu、Young Ho Kim、Sun-Hee Woo、Sang-Hun Jung

  DOI：10.1021/acsmedchemlett.5b00043

  日期：2015.7.9

  Chrysosplenol C (4',5,6-trihydroxy-3,3',7-tri-methoxyflavone) isolated from Miliusa balansae has unique structural features as a reversible inotropic agent independent of beta-adrenergic signaling and with selective activation of cardiac myosin ATPase. Hence, a series of chrysosplenol analogues were synthesized and explored for identification of pharmacophore that is essential for the increasing contractility in rat ventricular myocytes. Analogue 7-chloro-2-(3-hydroxypheny1)-3-methoxy-4H-chromen-4-one showed highly potent contractility (54.8% at 10 mu M) through activating cardiac myosin ATPase (38.7% at 10 mu M). Our systematic structure activity relationship study revealed that flavonoid nucleus of chrososplenol C appears to be an essential basic skeleton and hydrophobic substituent at position 7 of chromenone such as methoxy or chloro enhances the activity. Additionally, our ATPase study suggested that these chrysosplenol analogues have selectivity toward cardiac myosin activation. Thus, the novel flavonone with 3-/7-hydrophobic substituent and 3'-hydrogen bonding donor function is a novel scaffold for discovery of a new positive inotropic agent.