5,5',6,6'-tetramethoxybiphenyl-3,3'-dicarbaldehyde | 4482-29-5

• 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: 5,5',6,6'-tetramethoxybiphenyl-3,3'-dicarbaldehyde
• 英文别名: 3-(5-Formyl-2,3-dimethoxy-phenyl)-4,5-dimethoxy-benzaldehyde；3-(5-formyl-2,3-dimethoxyphenyl)-4,5-dimethoxybenzaldehyde
• CAS: 4482-29-5
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: VCSKREAXBWDNTH-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C(Solv: methanol (67-56-1))
• 沸点：
  456.8±45.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5',6,6'-tetramethoxybiphenyl-3,3'-dicarbaldehyde 在 sodium hydroxide 、 potassium permanganate 作用下， 生成 Dehydrodiveratrumsaeure
  参考文献：
  名称：

  与黑色素化学有关的研究。第七部分 尝试从3,4-二羟基苯乙胺和3,4-二羟基苯基丙氨酸合成黑色素时，可能的中间体合成羟基化的二吲哚基，联苯和二氢吲哚-2-羧酸

  摘要：

  描述了5,5'-，6,6'-和5,6'-双-（2-氨基乙基）-2,2'，3,3'-四羟基联苯，2,4-双-（3 1,4-二羟基苯基）丁烷-1,3-二胺和2,3-双-（3,4-二羟基苯基）丁烷-1,4-二胺二盐酸盐，5,5'-，6,6'-和5 ，6′-双-（2-氨基-2-羧乙基）-2，2′，3，3′-四羟基联苯和5，6-二羟基二氢吲哚-2-羧酸。

  DOI：

  10.1039/j39700000865
• 作为产物：
  描述：

  2,2',3,3'-tetramethoxy-5,5'-dimethyl biphenyl 在 2,2'-(1,2-肼二亚基)二[3-乙基-2,3-二氢-6-苯并噻唑磺酸 、 laccase 作用下， 以 水 为溶剂， 生成 5,5',6,6'-tetramethoxybiphenyl-3,3'-dicarbaldehyde
  参考文献：
  名称：

  The early oxidative biodegradation steps of residual kraft lignin models with laccase

  摘要：

  A number of model compounds resembling the fundamental bonding patterns of residual kraft lignin, including a series of stilbenes, were incubated with laccase from Trametes versicolor in the presence and absence of delignification 'mediators' ABTS and HBT. The condensed kraft lignin model compounds seem to undergo initial degradation by laccase mainly via benzylic oxidation, demethylation and hydroxylation reactions. Phenolic 5-5', diphenylmethane and alpha-5 lignin models were found to be degraded mainly via side-chain oxidation reactions. Among the models studied, a phenolic stilbene was found to be the most reactive, yielding several products showing side-chain oxidation/transposition, demethoxylation and hydroxylation reactions. Non-phenolic 5-5', diphenylmethane and stilbene model compounds were found unreactive even in the presence of the laccase-mediator system. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00173-4

文献信息

• Synthesis of 1-aryltetrahydroisoquinoline alkaloids and their analogs
  作者：Sh. N. Zhurakulov、V. I. Vinogradova、M. G. Levkovich

  DOI：10.1007/s10600-013-0507-2

  日期：2013.3

  Three alkaloids of the cryptostylin series and 20 monomolecular and 3 bimolecular 1-aryltetrahydroisoquinoline derivatives were prepared using the Picte–Spengler reaction.

  利用Pictet-Spengler反应制备了隐柱系列的三种生物碱以及20种单分子和3种双分子1-芳基四氢异喹啉衍生物。
• Synthesis and Studies of the Inhibitory Effect of Hydroxylated Phenylpropanoids and Biphenols Derivatives on Tyrosinase and Laccase Enzymes
  作者：Maria Antonietta Dettori、Davide Fabbri、Alessandro Dessì、Roberto Dallocchio、Paola Carta、Claudia Honisch、Paolo Ruzza、Donatella Farina、Rossana Migheli、Pier Andrea Serra、Roberto A. Pantaleoni、Xenia Fois、Gaia Rocchitta、Giovanna Delogu

  DOI：10.3390/molecules25112709

  日期：——

  the viability of the new compounds was assayed on PC12 cells, four of which showed a viability of roughly 80% at 40 µM. In silico studies on the crystal structure of laccase enzyme identified a hydroxylated biphenyl bearing a prenylated chain as the lead structure, which activated strong and effective interactions at the active site of the enzyme. These data were confirmed by in vivo experiments performed

  酪氨酸酶和漆酶活性受损会引起哺乳动物、昆虫和微生物生命周期中的严重问题。对这两种酶抑制剂的研究可能会导致发现增白剂、医药产品、抗褐变物质和用于控制有害昆虫和细菌的化合物。使用天然存在的化合物制备了一小部分具有苯丙烷和羟基化联苯核心的新型可逆酪氨酸酶和漆酶抑制剂，并通过分光光度法和电化学测定法测量了它们的活性。构建了基于酪氨酸酶和漆酶酶的生物传感器，用于检测蛋白质-配体相互作用的类型和半数最大抑制浓度 (IC50)。大多数抑制剂对酪氨酸酶的 IC50 为 20-423 nM，对漆酶的 IC50 为 23-2619 nM。由于传统酪氨酸酶和漆酶抑制剂的安全问题，在 PC12 细胞上测定了新化合物的活力，其中四种在 40 µM 下显示出大约 80% 的活力。对漆酶晶体结构的计算机模拟研究确定了带有异戊二烯化链的羟基化联苯作为先导结构，它在酶的活性位点激活了强大而有效的相互作用。这些数据通过在昆虫
• Process for preparing biphenyl compounds
  申请人：UNIVERSITÉ DE BORDEAUX

  公开号：US10155969B2

  公开（公告）日：2018-12-18

  The present invention relates to a process for preparing a compound having the formula (I), said process comprising the following steps: a) the addition of an oxygen source into a solution of a compound of formula (II), in a water-miscible solvent, b) the addition of a laccase in the solution obtained after step a); and c) the possible recovering of the compound of formula (I) thus obtained.

  本发明涉及一种制备具有化学式(I)的化合物的方法，该方法包括以下步骤：a)将氧源加入到具有化学式(II)的化合物的溶液中，溶剂为水溶性溶剂；b)将漆酶加入到步骤a)得到的溶液中；c)可能回收所得到的具有化学式(I)的化合物。
• Hydroxylated biphenyls as tyrosinase inhibitor: A spectrophotometric and electrochemical study
  作者：Paolo Ruzza、Pier Andrea Serra、Davide Fabbri、Maria Antonietta Dettori、Gaia Rocchitta、Giovanna Delogu

  DOI：10.1016/j.ejmech.2016.12.028

  日期：2017.1

  A small collection of C2-symmetry hydroxylated biphenyls was prepared by straightforward methods and the capability to act as inhibitors of tyrosinase has been evaluated by both spectrophotometric and electrochemical assays. Our attention was focused on the diphenolase activity of this enzyme characterized by the absence of the characteristic lag time of enzymatic reaction of its monophenolase activity

  通过简单的方法制备了少量的C 2对称羟基联苯，并且已通过分光光度法和电化学分析法评估了其作为酪氨酸酶抑制剂的能力。我们的注意力集中在该酶的双酚酶活性上，该酶的特征在于不存在其单酚酶活性的酶促反应的特征滞后时间。为了这个目的，我们评估了对酪氨酸酶的氧化天然能力Ò二酚基板ö醌分析酪氨酸酶生物传感器中咖啡酸溶液的UV-Vis光谱变化和阴极电流的减少。两种方法的结果均具有可比性。与已知的酪氨酸酶羟化联苯抑制剂化合物1相比，大多数化合物具有更高的抑制活性。
• Synthesis of Hydroxylated Biphenyl Derivatives Bearing an α,β‐Unsaturated Ketone as a Lead Structure for the Development of Drug Candidates against Malignant Melanoma
  作者：Maria Antonietta Dettori、Marina Pisano、Carla Rozzo、Giovanna Delogu、Davide Fabbri

  DOI：10.1002/cmdc.202000709

  日期：2021.3.18

  A small collection of C2‐symmetric hydroxylated biphenyl derivatives featuring an α,β‐unsaturated ketone as a lead structure was prepared, and the capacity of these compounds to act as antiproliferative agents against four human malignant melanoma cell lines was assayed. The prodrug approach was applied in order to improve the delivery of compounds into the cell by modulation of the phenolic hydroxy

  制备了一小部分以 α,β-不饱和酮为先导结构的 C 2对称羟基化联苯衍生物，并测定了这些化合物作为抗增殖剂对抗四种人类恶性黑色素瘤细胞系的能力。应用前药方法是为了通过调节酚羟基保护基团来改善化合物向细胞的递送。发现带有α,β-不饱和酮和酚-O-异戊二烯化链的羟基化联苯结构有助于分子的传递和与生物靶标的相互作用。四种化合物显示出抗增殖活性，导致 IC 50值在 1.2 至 2.8 μM 的范围内。