(Z)-2-(4-hydroxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one | 55794-17-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-2-(4-hydroxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one
• 英文别名: 4,6-dimethoxy-2-(4'-hydroxybenzylidene)benzofuran-3(2H)-one；4,6-dimethoxy-4’-hydroxyaurone；2-((Z)-4-hydroxy-benzylidene)-4,6-dimethoxy-benzofuran-3-one；2-((Z)-4-Hydroxy-benzyliden)-4,6-dimethoxy-benzofuran-3-on；(2Z)-2-[(4-hydroxyphenyl)methylene]-4,6-dimethoxy-benzofuran-3-one；(2Z)-2-[(4-hydroxyphenyl)methylidene]-4,6-dimethoxy-1-benzofuran-3-one
• CAS: 55794-17-7
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: DYITXOTTZQOBMZ-CHHVJCJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4-hydroxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 3(2H)-苯并呋喃酮,4,6-二羟基-2-[(4-羟基苯基)亚甲基]-,(2Z)-
  参考文献：
  名称：

  以Aurones为效应子研究蘑菇和细菌酪氨酸酶之间的结合位同源性

  摘要：

  更光明的未来： Aurones已被确定为黑色素生物合成的抑制剂。在这项研究中，对蘑菇和细菌酪氨酸酶（TyM和TyB）上的24种金质进行了评估。该化合物充当两种酶的抑制剂，底物或激活剂。我们的结果强调了在同一分子下TyM和TyB之间行为的异同。

  DOI：

  10.1002/cbic.201402003
• 作为产物：
  描述：

  在 盐酸 作用下， 反应 4.0h， 以43%的产率得到(Z)-2-(4-hydroxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one
  参考文献：
  名称：

  Dimethoxyaurones：ABCG2（乳腺癌抗性蛋白）的有效抑制剂。

  摘要：

  通过将4，6-二甲氧基苯并呋喃-3（2H）-1与各种苯甲醛在碱催化的醛醇缩合反应中反应，合成了一系列4,6-二甲氧基金错误。根据光谱和晶体学数据将AZ构型分配给了光环。测试了金黄色素在体外调节ABCG2（乳腺癌抗性蛋白）介导的多药抗性的能力。几个成员（0.5 microM）增加了用ABCG2转染的人乳腺癌细胞（MDA-MB-231）中米托蒽醌（MX）的积累，并使这些细胞对MX的细胞毒性作用重新敏感。在再敏化试验中，0.5 microM的金黄色素使转染细胞对MX的抗性降至亲代细胞的两倍，超过在相同浓度下测试的泛黄霉素C（FTC）。金黄色素（10 microM）还增加了钙黄绿素-AM在用ABCB1（P-糖蛋白）转染的MDCKII / MDR1细胞中的蓄积，其水平与在相同浓度下测试的维拉帕米相当。结构活性分析表明，对于ABCG2抑制作用，金质模板中亚苄基环B的取代作用不那么重要，对于具有未取代环

  DOI：

  10.1016/j.ejps.2008.07.008

文献信息

• Synthesis of structurally diverse biflavonoids
  作者：Tze Jing Sum、Tze Han Sum、Warren R.J.D. Galloway、David G. Twigg、Joe J. Ciardiello、David R. Spring

  DOI：10.1016/j.tet.2018.05.003

  日期：2018.9

  a growing interest in synthetic approaches that can provide access to structurally novel biflavonoids so that the biological usefulness of this compound class can be more fully investigated. Herein, we report upon the exploration of strategies based around Suzuki-Miyaura cross-coupling and alcohol methylenation for the synthesis of two classes of biflavonoids: (i) rare ‘hybrid’ derivatives containing

  合成的双黄酮类化合物与有趣的生物学活性有关，但在药物发现中仍缺乏很好的探索。近年来，目睹了对合成方法的日益增长的兴趣，这些方法可以提供结构新颖的双黄酮类化合物，因此可以更充分地研究此类化合物的生物学用途。在本文中，我们报告了基于铃木-宫浦交叉偶联和醇甲基化的策略，用于合成两类双黄酮类化合物：（i）含有属于不同亚类的类黄酮单体的稀有“杂化”衍生物，以及（ii）同二聚体化合物，其中两个类黄酮单体通过亚甲二氧基连接。
• Method of cosmetic depigmentation care by applying at least one aurone
  申请人：Perrier Eric

  公开号：US20060228313A1

  公开（公告）日：2006-10-12

  at least one aurone or a natural or synthetic derivative of aurone, or an analogue of aurone, in which the independent phenyl ring can be substituted by a heterocycle of pyrrole, imidazole, triazole, pyridine, furan, or thiophene type, is disclosed as a cosmetic agent, or as an active substance, for the manufacture either of a cosmetic composition, or of a pharmaceutical composition, notably a dermatological composition, having a melanogenesis-inhibiting activity or a depigmenting activity, or an anti-tyrosinase activity.

  本发明公开了至少一种黄酮类化合物或黄酮的天然或合成衍生物，或黄酮的类似物，其中独立的苯环可以被吡咯、咪唑、三唑、吡啶、呋喃或噻吩类的杂环取代，作为化妆品成分或活性物质，用于制备化妆品组合物或制药组合物，特别是皮肤科组合物，具有抑制黑色素生成或脱色活性或抗酪氨酸酶活性。
• A method of cosmetic depigmentation care by applying at least one aurone
  申请人：ENGELHARD LYON

  公开号：EP1709964A2

  公开（公告）日：2006-10-11

  At least one aurone or a natural or synthetic derivative of aurone, or an analogue of aurone, in which the independent phenyl ring can be substituted by a heterocycle of pyrrole, imidazole, triazole, pyridine, furan, or thiophene type, is disclosed as a cosmetic agent, or as an active substance, for the manufacture either of a cosmetic composition, or of a pharmaceutical composition, notably a dermatological composition, having a melanogenesis-inhibiting activity or a depigmenting activity, or an anti-tyrosinase activity.

  公开了至少一种脲或脲的天然或合成衍生物，或脲的类似物，其中独立的苯基环可以被吡咯、咪唑、三唑、吡啶、呋喃或噻吩类型的杂环取代，作为化妆品剂、或活性物质，用于制造具有黑色素生成抑制活性或脱色活性或抗酪氨酸酶活性的化妆品组合物或药物组合物，特别是皮肤科组合物。
• Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR
  作者：Chong-Yew Lee、Eng-Hui Chew、Mei-Lin Go

  DOI：10.1016/j.ejmech.2010.03.023

  日期：2010.7

  The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P) H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E-LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity. (c) 2010 Elsevier Masson SAS. All rights reserved.
• DiVittorio, Rendiconti - Istituto superiore di sanita, 1958, vol. 21, p. 418,428
  作者：DiVittorio

  DOI：——

  日期：——