6-formyl-2,3,4-trimethoxyphenylboronic acid | 1035933-58-4

• 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: 6-formyl-2,3,4-trimethoxyphenylboronic acid
• 英文别名: (6-Formyl-2,3,4-trimethoxyphenyl)boronic acid；(6-formyl-2,3,4-trimethoxyphenyl)boronic acid
• CAS: 1035933-58-4
• 化学式: C₁₀H₁₃BO₆
• 分子量: 240.021
• InChiKey: KPTKLIIFACPAKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-formyl-2,3,4-trimethoxyphenylboronic acid 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 、 溶剂黄146 、 正丁胺 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 72.0h， 生成 (E)-2,2'-di(2-methylnitrovinnyl)-4',5'-methylenedioxy-4,5,6-trimethoxybiphenyl
  参考文献：
  名称：

  Discovery of novel antitumor dibenzocyclooctatetraene derivatives and related biphenyls as potent inhibitors of NF-κB signaling pathway

  摘要：

  Several dibenzocyclooctatetraene derivatives (5-7) and related biphenyls (8-11) were designed, synthesized, and evaluated for inhibition of cancer cell growth and the NF-kappa B signaling pathway. Compound 5a, a dibenzocyclooctatetraene succinimide, was discovered as a potent inhibitor of the NF-kappa B signaling pathway with significant antitumor activity against several human tumor cell lines (GI(50) 1.38-1.45 mu M) and was more potent than paclitaxel against the drug-resistant KBvin cell line. Compound 5a also inhibited LPS-induced NF-kappa B activation in RAW264.7 cells with an IC50 value of 0.52 mu M, prevented I kappa B-alpha degradation and p65 nuclear translocation, and suppressed LPS-induced NO production in a dose-dependent manner. The antitumor data in cellular assays indicated that relative positions and types of substituents on the dibenzocyclooctatetraene or acyclic biphenyl as well as torsional angles between the two phenyls are of primary importance to antitumor activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.018
• 作为产物：
  描述：

  3,4,5-三甲氧基-2-溴苯甲醛 在 叔丁基锂 、 硼酸三甲酯 、 盐酸 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 0.17h， 以97%的产率得到6-formyl-2,3,4-trimethoxyphenylboronic acid
  参考文献：
  名称：

  （A R，7 S）-（-）- N-乙酰胆碱醇及其与环状RGD肽的缀合物的合成

  摘要：

  基于Suzuki-Miyaura偶联生成联芳基药效团，描述了（-）- N-乙酰基胆酚的不对称合成。在化学计量的手性路易斯酸（TarB–NO 2）存在下，使用硼氢化锂通过不对称还原二苯并亚砜酮衍生物24引入了唯一的不对称中心。一个α之间的缀合物V β 3整联蛋白结合环肽C [RGDfK]和colchinol（己二酰接头）与一个目标合成以选择性地递送colchinol实体瘤。

  DOI：

  10.1016/j.tet.2008.01.130

文献信息

• An Efficient Combinatorial Synthesis of Allocolchicine Analogues via a Triple Cascade Reaction and their Evaluation as Inhibitors of Insulin Aggregation
  作者：Subhendu Bhowmik、Shruti Khanna、Kumkum Srivastava、Mohammad Hasanain、Jayanta Sarkar、Sandeep Verma、Sanjay Batra

  DOI：10.1002/cmdc.201300302

  日期：2013.11

  A controlled cascade: A divergent, diastereoselective and efficient one‐pot synthesis of allocolchicinoids via a cascade Suzuki–Michael addition–Carbocyclization sequence is described. The utility of the compounds as possible inhibitors of insulin aggregation is also presented.

  受控级联反应：描述了通过级联的Suzuki-Michael加成-碳环化序列进行的发散，非对映选择性和有效的一锅法制备类油醇类化合物。还提出了化合物作为胰岛素聚集的可能抑制剂的用途。
• A novel synthetic dibenzocyclooctadiene lignan analog XLYF-104-6 attenuates lipopolysaccharide-induced inflammatory response in RAW264.7 macrophage cells and protects BALB/c mice from sepsis
  作者：Chunping Gu、Fang-Lin Yu、Le Yu、Xiao-Yang He、Desheng Zhong、Longgang He、Longyun Lv、Lan Xie、Shuwen Liu

  DOI：10.1016/j.ejphar.2014.01.019

  日期：2014.4

  The wide range of inflammation mechanisms under control by NF-kappa B makes this pathway as an attractive target for new anti-inflammatory drugs. Herein, we showed that a new dibenzocyclooctadiene lignan analog XLYF-104-6, with a chemical name of 1,2,3,10,11-pentamethoxydibenzocycloocta-6,7-[c] pyrrole-1,3-dione, inhibited lipopolysaccharide (LPS)-induced NF-kappa B activation in RAW264.7 cells through preventing I kappa B alpha degradation and p65 nuclear translocation. The inhibitory activity of this compound on NF-kappa B activation contributes to the reduction of LPS-induced TNF-alpha and IL-6 productions. Notably, XLYF-104-6 suppressed LPS-induced iNOS expression and NO production in a NF-kappa B independent manner, since IKK inhibitor BAY 11-7082 has failed to exert similar inhibitory effect on iNOS expression and NO production. In addition, XLFY-104-6 also exerted anti-inflammatory action in endotoxemic mice by decreasing plasma LPS-induced TNF-alpha and IL-1 beta levels as well as increasing plasma LPS-induced IL-10 concentrations. These findings suggest XLYF-104-6 could act as a leading compound for developing a potential anti-inflammatory drug. (C) 2014 Published by Elsevier B.V.
• A synthesis of (aR,7S)-(−)-N-acetylcolchinol and its conjugate with a cyclic RGD peptide
  作者：Gilbert Besong、Denis Billen、Indu Dager、Philip Kocienski、Eric Sliwinski、Lik Ren Tai、F. Thomas Boyle

  DOI：10.1016/j.tet.2008.01.130

  日期：2008.5

  An asymmetric synthesis of (−)-N-acetylcolchinol is described based on a Suzuki–Miyaura coupling to generate the biaryl pharmacophore. The sole asymmetric centre was introduced by an asymmetric reduction of a dibenzosuberone derivative 24 using lithium borohydride in the presence of stoichiometric amounts of a chiral Lewis acid (TarB–NO2). A conjugate between an αVβ3 integrin-binding cyclic peptide

  基于Suzuki-Miyaura偶联生成联芳基药效团，描述了（-）- N-乙酰基胆酚的不对称合成。在化学计量的手性路易斯酸（TarB–NO 2）存在下，使用硼氢化锂通过不对称还原二苯并亚砜酮衍生物24引入了唯一的不对称中心。一个α之间的缀合物V β 3整联蛋白结合环肽C [RGDfK]和colchinol（己二酰接头）与一个目标合成以选择性地递送colchinol实体瘤。
• Discovery of novel antitumor dibenzocyclooctatetraene derivatives and related biphenyls as potent inhibitors of NF-κB signaling pathway
  作者：Fang-Lin Yu、Xiao-Yang He、Chunping Gu、Emika Ohkoshi、Li-Ting Wang、Sheng-Biao Wang、Chin-Yu Lai、Le Yu、Susan L. Morris-Natschke、Kuo-Hsiung Lee、Shuwen Liu、Lan Xie

  DOI：10.1016/j.bmc.2013.11.018

  日期：2014.1

  Several dibenzocyclooctatetraene derivatives (5-7) and related biphenyls (8-11) were designed, synthesized, and evaluated for inhibition of cancer cell growth and the NF-kappa B signaling pathway. Compound 5a, a dibenzocyclooctatetraene succinimide, was discovered as a potent inhibitor of the NF-kappa B signaling pathway with significant antitumor activity against several human tumor cell lines (GI(50) 1.38-1.45 mu M) and was more potent than paclitaxel against the drug-resistant KBvin cell line. Compound 5a also inhibited LPS-induced NF-kappa B activation in RAW264.7 cells with an IC50 value of 0.52 mu M, prevented I kappa B-alpha degradation and p65 nuclear translocation, and suppressed LPS-induced NO production in a dose-dependent manner. The antitumor data in cellular assays indicated that relative positions and types of substituents on the dibenzocyclooctatetraene or acyclic biphenyl as well as torsional angles between the two phenyls are of primary importance to antitumor activity. (C) 2013 Elsevier Ltd. All rights reserved.