noraucuparin | 1188276-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: noraucuparin
• 英文别名: 3-methoxy-5-phenylbenzene-1,2-diol
• CAS: 1188276-88-1
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: CDSGSEYGSWGVOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二氯甲烷 、 noraucuparin 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50 %的产率得到4-methoxy-6-phenylbenzo[d] [1,3]dioxole
  参考文献：
  名称：

  天然植物抗毒素启发了新联苯的发现，作为治疗侵袭性真菌感染的有效抗真菌剂

  摘要：

  为了发现源自天然来源的新颖有效的抗真菌剂，设计、合成了一系列基于天然联苯植物抗毒素的新型联苯，并评估了其对四种入侵真菌的抗真菌活性通过修饰去核桃苷（一种著名的联苯植物抗毒素）的两个苯环，发现了一些具有显着抗真菌活性的有前景的化合物。值得注意的是，化合物23a、23e和23h表现出有效的活性和广泛的抗真菌谱，MIC 低至0.25-16 μg/mL，比先导化合物去核桃苷的效力强 8-256 倍。特别是，它们对新型隐球菌表现出与阳性对照两性霉素 B 相当的效力。还讨论了一些有趣的结构-活性关系。初步机理研究表明，化合物23h可能通过破坏真菌细胞膜来实现其快速杀菌活性。此外，化合物23h新型隐球菌的部分毒力因子具有显着的抑制作用，对正常人体细胞毒性低，具有良好的药代动力学和类药特性。上述结果证明，从天然植物抗毒素中开发新的抗真菌候选药物是一个光明且有前途的策略。

  DOI：

  10.1016/j.ejmech.2023.115842
• 作为产物：
  描述：

  5-溴-2-羟基-3-甲氧基苯甲醛 在 palladium 10% on activated carbon 、 双氧水 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 生成 noraucuparin
  参考文献：
  名称：

  Suzuki–Miyaura Coupling of Halophenols and Phenol Boronic Acids: Systematic Investigation of Positional Isomer Effects and Conclusions for the Synthesis of Phytoalexins from Pyrinae

  摘要：

  The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4'-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.

  DOI：

  10.1021/jo500675a

文献信息

• <i>ortho</i>-Quinol Acetate Chemistry: Reactivity toward Aryl-Based Nucleophiles and Applications to the Synthesis of Natural Products
  作者：Simon Companys、Laurent Pouységu、Philippe A. Peixoto、Stefan Chassaing、Stéphane Quideau

  DOI：10.1021/acs.joc.7b00250

  日期：2017.4.7

  Two model ortho-quinol acetates were easily prepared by iodane-mediated acetoxylative phenol dearomatization and evaluated for their reactivity toward various aryl-based nucleophiles, i.e., aryl metallic reagents and phenolic derivatives. Novel modes of reactivity, allowing the formation of biaryl linkages, were revealed and here exploited for the synthesis of two natural phenolics.

  可以通过碘介导的乙酰氧基化苯酚脱芳香化反应轻松制备两种模型的邻苯二甲酸邻苯二酚乙酸酯，并评估其对各种基于芳基的亲核试剂（即芳基金属试剂和酚衍生物）的反应性。揭示了允许形成联芳基键的新型反应模式，并在此用于合成两种天然酚类。
• Biosynthesis of the biphenyl phytoalexin aucuparin in Sorbus aucuparia cell cultures treated with Venturia inaequalis
  作者：Mohammed N.A. Khalil、Till Beuerle、Andreas Müller、Ludger Ernst、Vijaya B.R. Bhavanam、Benye Liu、Ludger Beerhues

  DOI：10.1016/j.phytochem.2013.09.003

  日期：2013.12

  Aucuparin is the most widely distributed biphenyl phytoalexin in the rosaceous subtribe Pyrinae, which includes the economically important fruit trees apple and pear. The biphenyl scaffold is formed by biphenyl synthase, which catalyzes biosynthesis of 3,5-dihydroxybiphenyl. Conversion of this precursor to aucuparin (3,5-dimethoxy-4-hydroxybiphenyl) was studied in cell cultures of Sorbus aucuparia after treatment with an elicitor preparation from the scab-causing fungus Venturia inaequalis. The sequence of the biosynthetic steps detected was O-methylation - 4-hydroxylation - O-methylation. The two alkylation reactions were catalyzed by distinct methyltransferases, which differed in pH and temperature optima as well as stability. Biphenyl 4-hydroxylase was a microsomal cytochrome P450 monooxygenase, whose activity was appreciably decreased by the addition of established P450 inhibitors. When fed to V. inaequalis-treated S. aucuparia cell cultures, radioactively labeled 3,5-dihydroxybiphenyl was not only incorporated into aucuparin but also into the dibenzofuran eriobofuran, the accumulation of which paralleled that of aucuparin. However, biphenyl 2'-hydroxylase activity proposed to be involved in dibenzofuran formation was detected in neither microsomes nor cell-free extracts in the presence of NADPH and 2-oxoglutarate, respectively. Nevertheless, a basis for studying biphenyl biosynthesis at the gene level is provided. (C) 2013 Elsevier Ltd. All rights reserved.
• CN115784848
  申请人：——

  公开号：——

  公开（公告）日：——
• Suzuki–Miyaura Coupling of Halophenols and Phenol Boronic Acids: Systematic Investigation of Positional Isomer Effects and Conclusions for the Synthesis of Phytoalexins from Pyrinae
  作者：Bernd Schmidt、Martin Riemer

  DOI：10.1021/jo500675a

  日期：2014.5.2

  The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4'-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.
• Natural phytoalexins inspired the discovery of new biphenyls as potent antifungal agents for treatment of invasive fungal infections
  作者：Jian-Chuan Liu、Jian Yang、Shu-Xin Lei、Ming-Fan Wang、Yan-Ni Ma、Rui Yang

  DOI：10.1016/j.ejmech.2023.115842

  日期：2023.12

  discovering novel and effective antifungal agents derived from natural sources, a series of new biphenyls based on natural biphenyl phytoalexins were designed, synthesized and evaluated for their antifungal activities against four invasive fungi. By modifying the two benzene rings of noraucuparin, a well-known biphenyl phytoantitoxin, some promising compounds with remarkable antifungal activity were discovered

  为了发现源自天然来源的新颖有效的抗真菌剂，设计、合成了一系列基于天然联苯植物抗毒素的新型联苯，并评估了其对四种入侵真菌的抗真菌活性通过修饰去核桃苷（一种著名的联苯植物抗毒素）的两个苯环，发现了一些具有显着抗真菌活性的有前景的化合物。值得注意的是，化合物23a、23e和23h表现出有效的活性和广泛的抗真菌谱，MIC 低至0.25-16 μg/mL，比先导化合物去核桃苷的效力强 8-256 倍。特别是，它们对新型隐球菌表现出与阳性对照两性霉素 B 相当的效力。还讨论了一些有趣的结构-活性关系。初步机理研究表明，化合物23h可能通过破坏真菌细胞膜来实现其快速杀菌活性。此外，化合物23h新型隐球菌的部分毒力因子具有显着的抑制作用，对正常人体细胞毒性低，具有良好的药代动力学和类药特性。上述结果证明，从天然植物抗毒素中开发新的抗真菌候选药物是一个光明且有前途的策略。