2,2'-diformyl-3,4,4',5,5'-pentamethoxybiphenyl

• 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: 2,2'-diformyl-3,4,4',5,5'-pentamethoxybiphenyl
• 英文别名: 2,2'-diformyl-4,4',5,5',6-pentamethoxybiphenyl；2,2'-diformyl-4,4',5,5',6-pentamethoxydiphenyl；2-(2-Formyl-4,5-dimethoxyphenyl)-3,4,5-trimethoxybenzaldehyde
• 化学式: C₁₉H₂₀O₇
• 分子量: 360.364
• InChiKey: DMYNVXXXSOGUIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,4-dimethyl but-2-enedioate 、 2,2'-diformyl-3,4,4',5,5'-pentamethoxybiphenyl 在 三丁基膦 、 哌啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 26.0h， 以41%的产率得到(5Z,7Z)-6,7-dicarbomethoxy-1,2,3,10,11-pentamethoxydibenzocyclooctatetraene
  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：

  1,2,3,9,10-pentamethoxy-5,7-dihydrodibenzoxepine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以46%的产率得到2,2'-diformyl-3,4,4',5,5'-pentamethoxybiphenyl
  参考文献：
  名称：

  Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent

  摘要：

  The hypervalent iodine(III)-induced intramolecular biaryl coupling reaction of phenol ether derivatives (nonphenolic derivatives) was investigated with the aim of preparing various dibenzo heterocyclic compounds. 1,3-Diarylpropanes (1a-e), N-benzyl-N-phenethylamines (2a-c) and N,N-dibenzylamines (3a-e) react with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), containing BF3. Et2O in CH2Cl2 to give the biaryl coupling products (4-6) in good yield. As an application of the reaction, we examined the synthesis of oxygen- and sulfur-containing dibenzoheterocyclic compounds (12-15), whose side chain moiety could be easily cleaved by the known method to give 2,2'-substituted biphenyl compounds (16-18).

  DOI：

  10.1021/jo980704f

文献信息

• AMBIENT-TEMPERATURE ULLMAN REACTION: 4,5,4',5'-TETRAMETHOXY-1,1'-BIPHENYL-2,2'-DICARBOXALDEHYDE
  作者：Ziegler、Fowler、Rodgers、Wester

  DOI：10.15227/orgsyn.065.0108

  日期：——
• 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.
• ZIEGLER, F. E.;FOWLER, K. W.;RODGERS, W. B.;WESTER, R. T., ORG. SYNTH., NEW YORK ETC.,(1987) C. 108-118
  作者：ZIEGLER, F. E.、FOWLER, K. W.、RODGERS, W. B.、WESTER, R. T.

  DOI：——

  日期：——
• 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.
• Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent
  作者：Takeshi Takada、Mitsuhiro Arisawa、Michiyo Gyoten、Ryuji Hamada、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1021/jo980704f

  日期：1998.10.1

  The hypervalent iodine(III)-induced intramolecular biaryl coupling reaction of phenol ether derivatives (nonphenolic derivatives) was investigated with the aim of preparing various dibenzo heterocyclic compounds. 1,3-Diarylpropanes (1a-e), N-benzyl-N-phenethylamines (2a-c) and N,N-dibenzylamines (3a-e) react with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), containing BF3. Et2O in CH2Cl2 to give the biaryl coupling products (4-6) in good yield. As an application of the reaction, we examined the synthesis of oxygen- and sulfur-containing dibenzoheterocyclic compounds (12-15), whose side chain moiety could be easily cleaved by the known method to give 2,2'-substituted biphenyl compounds (16-18).