2,6-bis(2,3-dimethoxybenzylidene)cyclohexanone | 69662-18-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,6-bis(2,3-dimethoxybenzylidene)cyclohexanone
• 英文别名: 2,6-Bis[(2,3-dimethoxyphenyl)methylidene]cyclohexan-1-one
• CAS: 69662-18-6
• 化学式: C₂₄H₂₆O₅
• mdl: MFCD03465583
• 分子量: 394.467
• InChiKey: NCHAALDGNRJQFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis(2,3-dimethoxybenzylidene)cyclohexanone 在 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  小说 螺旋体基二亚磷酸酯 配体 为了 加氢甲酰化 末端烯烃和内部烯烃

  摘要：

  旋风基二亚磷酸酯 配体已经开发出了铑催化的加氢甲酰化反应。在优化的反应条件下，末端加氢甲酰化反应中的周转数（TON）最高为2.4×10 4，线性与支化比（l / b）最高为93烯烃。这催化剂 还发现在某些内部的异构化-加氢甲酰化中有效 烯烃。

  DOI：

  10.1039/c3cy00187c
• 作为产物：
  描述：

  环己酮 、 2,3-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2,6-bis(2,3-dimethoxybenzylidene)cyclohexanone
  参考文献：
  名称：

  Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes

  摘要：

  摘要 目的 合成了一系列43个姜黄素二芳基戊酮类似物，并评估它们对体外吞噬细胞化学发光和趋化活性的抑制作用。 方法 使用基于流明的化学发光测定法评估化合物对人全血和分离的人多形核白细胞（PMNs）呼吸爆发的影响，并利用Boyden室技术研究它们对PMNs趋化迁移的影响。 主要发现 化合物6、17、25和30在PMNs的氧化爆发上表现出显著的抑制活性。在两个苯环的2和5位置有甲氧基基团，以及在4和2位置分别有甲氧化和氟化基团的存在，可能会显著促进它们对活性氧化物种的抑制活性。化合物7、17、18、24和32显示出对PMNs趋化迁移的强烈抑制作用。在环己酮二芳基戊酮类似物的两个苯环的不同位置进行氯化，导致化合物对PMN迁移具有强效抑制作用。 结论 结果表明，这些二芳基戊酮类似物中的一些能够调节吞噬细胞的先天免疫反应的不同步骤，强调它们作为新的免疫调节剂来源的潜力。

  DOI：

  10.1111/j.2042-7158.2011.01423.x

文献信息

• Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes
  作者：Ibrahim Jantan、Syed Nasir Abbas Bukhari、Nordin Haji Lajis、Faridah Abas、Lam Kok Wai、Malina Jasamai

  DOI：10.1111/j.2042-7158.2011.01423.x

  日期：2012.2.6

  A series of 43 curcumin diarylpentanoid analogues were synthesized and evaluated for their inhibitory effects on the chemiluminescence and chemotactic activity of phagocytes in vitro.

  The effects of the compounds on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) were evaluated using a luminol-based chemiluminescence assay and their effect on chemotactic migration of PMNs was investigated using the Boyden chamber technique.

  Compounds 6, 17, 25 and 30 exhibited significant inhibitory activity on the oxidative burst of PMNs. The presence of methoxy groups at positions 2 and 5, and methoxylation and fluorination at positions 4 and 2 of both phenyl rings, respectively, may contribute significantly to their reactive oxygen species inhibition activity. Compounds 7, 17, 18, 24 and 32 showed strong inhibition of the chemotaxis migration of PMNs. Chlorination at various positions of both phenyl rings of cyclohexanone diarylpentanoid resulted in compounds with potent inhibitory effects on PMN migration.

  The results suggest that some of these diarylpentanoid analogues are able to modulate the innate immune response of phagocytes at different steps, emphasizing their potential as a source of new immunomodulatory agents.

  摘要 目的 合成了一系列43个姜黄素二芳基戊酮类似物，并评估它们对体外吞噬细胞化学发光和趋化活性的抑制作用。 方法 使用基于流明的化学发光测定法评估化合物对人全血和分离的人多形核白细胞（PMNs）呼吸爆发的影响，并利用Boyden室技术研究它们对PMNs趋化迁移的影响。 主要发现 化合物6、17、25和30在PMNs的氧化爆发上表现出显著的抑制活性。在两个苯环的2和5位置有甲氧基基团，以及在4和2位置分别有甲氧化和氟化基团的存在，可能会显著促进它们对活性氧化物种的抑制活性。化合物7、17、18、24和32显示出对PMNs趋化迁移的强烈抑制作用。在环己酮二芳基戊酮类似物的两个苯环的不同位置进行氯化，导致化合物对PMN迁移具有强效抑制作用。 结论 结果表明，这些二芳基戊酮类似物中的一些能够调节吞噬细胞的先天免疫反应的不同步骤，强调它们作为新的免疫调节剂来源的潜力。
• Asymmetrical meta-methoxylated diarylpentanoids: Rational design, synthesis and anti-cancer evaluation in-vitro
  作者：Sze Wei Leong、Suet Lin Chia、Faridah Abas、Khatijah Yusoff

  DOI：10.1016/j.ejmech.2018.08.039

  日期：2018.9

  In the present study, a series of forty-five asymmetrical meta-methoxylated diarylpentanoids have been synthesized, characterized and evaluated for their in-vitro anti-cancer potential. Among the forty-five analogs, three compounds (20, 33 and 42) have been identified as lead compounds due to their excellent inhibition against five human cancer cell lines including SW620, A549, EJ28, HT1080 and MCF-7. Structure-activity relationship study on cytotoxicity of tested compounds suggested that the presence of meta-oxygenated phenyl ring played a critical role in enhancing their cytotoxic effects. Compounds 33 and 42 in particular, exhibited strongest cytotoxicity against tested cell lines with the IC50 values ranging from 1.1 to 4.3 M. Subsequent colony formation assay on SW620 cell line showed that both compounds 33 and 42 possessed strong anti-proliferative activity. In addition, flow cytometry based experiments revealed that these compounds could trigger intracellular ROS production thus inducing G2/M-phase cell arrest and apoptosis. All these results suggested that poly meta-oxygenated diarylpentnoid is a promising scaffold which deserved further modification and investigation in the development of natural product based anti-cancer drug. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents
  作者：Guang Liang、Lili Shao、Yi Wang、Chengguang Zhao、Yanhui Chu、Jian Xiao、Yu Zhao、Xiaokun Li、Shulin Yang

  DOI：10.1016/j.bmc.2008.10.044

  日期：2009.3

  Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modi. cations of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically. (C) 2009 Published by Elsevier Ltd.
• Novel spiroketal-based diphosphite ligands for hydroformylation of terminal and internal olefins
  作者：Xiaofei Jia、Zheng Wang、Chungu Xia、Kuiling Ding

  DOI：10.1039/c3cy00187c

  日期：——

  Spiroketal-based diphosphite ligands have been developed for the rhodium-catalyzed hydroformylation reaction. Under the optimized reaction conditions, a turnover number (TON) of up to 2.4 × 104 and a linear to branched ratio (l/b) of up to 93 were obtained in the hydroformylation of terminal olefins. The catalysts were also found to be effective in the isomerization–hydroformylation of some internal olefins.

  旋风基二亚磷酸酯 配体已经开发出了铑催化的加氢甲酰化反应。在优化的反应条件下，末端加氢甲酰化反应中的周转数（TON）最高为2.4×10 4，线性与支化比（l / b）最高为93烯烃。这催化剂 还发现在某些内部的异构化-加氢甲酰化中有效 烯烃。
• Effects of Novel Diarylpentanoid Analogues of Curcumin on Secretory Phospholipase A₂, Cyclooxygenases, Lipo-oxygenase, and Microsomal Prostaglandin E Synthase-1
  作者：Waqas Ahmad、Endang Kumolosasi、Ibrahim Jantan、Syed N. A. Bukhari、Malina Jasamai

  DOI：10.1111/cbdd.12280

  日期：2014.6

  diarylpentanoid curcumin analogues 5, 6, 7, and 13 demonstrated higher inhibition of microsomal prostaglandin E synthase‐1 activity with IC50 ranging from 2.41 to 4.48 μm, which was less than that of curcumin. The present results suggest that some of these diarylpentanoid analogues were able to inhibit the activity of these enzymes. This raises the possibility that diarylpentanoid analogues of curcumin might

  花生四烯酸及其代谢物由于其在炎症中的重要作用而引起了人们的关注。抑制花生四烯酸代谢中涉及的酶被认为是协同的抗炎作用。合成了一系列新型姜黄素二芳基戊烷类似物，并评估了它们对分泌性磷脂酶A 2，环加氧酶，大豆脂加氧酶以及微粒体前列腺素E合酶-1的抑制作用。之间的姜黄素类似物，化合物3，6，9，12，和17显示出分泌的磷脂酶A的强抑制2活性，以IC 50值范围从5.89到11.02  μ米。七姜黄素类似物1，3，6，7，9，11，和12环氧合酶-2的抑制表现出与IC 50值在46.11至94.86  μ米，这明显高于姜黄素的低。化合物3，6，7，12，和17对脂氧合酶的活性有很强的抑制作用。diarylpentanoid姜黄素类似物对微粒体前列腺素E合酶-1活性的初步筛选表明，4个diarylpentanoid姜黄素类似物5，6，7，和13表现出较高的抑制微粒体前列腺素E合酶-1活性的带IC 50范围从2