2,6-bis(3,4,5-trimethoxyphenylmethylene)cyclohexanone

• 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(3,4,5-trimethoxyphenylmethylene)cyclohexanone
• 英文别名: 2,6-bis(3,4,5-trimethoxybenzylidene)cyclohexanone；2,6-di(3,4,5-trimethoxybenzylidene)cyclohexanone；2,6-bis[(3,4,5-trimethoxyphenyl)methylidene]cyclohexan-1-one
• 化学式: C₂₆H₃₀O₇
• mdl: MFCD01306193
• 分子量: 454.52
• InChiKey: OXIWSGTZUCVQPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,6-bis(3,4,5-trimethoxyphenylmethylene)cyclohexanone 在 水 、 碘 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 (E)-8-[(3,4,5-trimethoxyphenyl)methylidene]-2-oxo-4-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-chromene-3-carbonitrile
  参考文献：
  名称：

  新型双环吡喃-2-酮体系的多组分合成

  摘要：

  基于环己酮与丙二腈和芳香醛的组合，开发了一种用于合成一系列新的吡喃-2-酮产品的一锅法。反应在相对较短的时间内在升高的温度下在含水醇介质中发生，通过容器中的自发沉淀直接产生产物。芳族吡喃-2-酮体系的最终形成在分子碘催化下原位发生。对反应的监测表明相应的双亚芳基和氨基-4 H-色烯中间体在该过程中的干预。这些中间体分别合成并转化为相同的最终产物，以支持反应通过建议的机制进行。 图形概要

  DOI：

  10.1007/s00706-022-02923-x
• 作为产物：
  描述：

  环己酮 、 3,4,5-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 2,6-bis(3,4,5-trimethoxyphenylmethylene)cyclohexanone
  参考文献：
  名称：

  一些异烟酸酰肼掺入的新型吲唑的计算机合成、生物学特征和 MMP-9 抑制活性

  摘要：

  本研究报道了异烟酸酰肼的合成，掺入7-(取代的苄基)-3-芳基-1-(吡啶-4-基)-甲酮)-2,3,4,5,6,7-六氢-1H -来自取代的查尔酮的吲唑。查耳酮是通过环己酮与取代的芳香醛通过克莱森-施密特法反应合成的。IR、1H NMR 和质谱研究用于表征合成的化合物。计算机分析用于预测合成化合物的生物活性。PASS 计算机程序预测所有标题化合物本质上都具有抗炎作用。采用明胶酶谱法筛选所有合成化合物的MMP-9抑制活性。在所有合成的化合物B1、B3、B4和B9中表现出显着的活性，而其余合成的化合物B2、B5、B6、B7和B8表现出轻度至中度的抗炎活性。

  DOI：

  10.14233/ajchem.2023.27591

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。
• Mechanistic investigations on substituted benzene sulphonamides as apoptosis inducing anticancer agents
  作者：Akhila Mettu、Venu Talla、Soujanya Thumma、Subhashini Naikal James Prameela

  DOI：10.1016/j.bioorg.2019.103539

  日期：2020.1

  than 1 µM in most of the tested cell lines. Further, compound A2 also induced apoptosis in DU-145 cells as exemplified from DAPI staining, Annexin V-FITC assay, ROS generation and mitochondrial membrane alteration studies. The above studies depict the synthesized compound A2 as potent anticancer agent with the ability to induce apoptosis in prostate cancerous cells.

  在开发具有靶向作用的强效细胞毒性化合物的方法中，采用系统方法来设计和初步合成母体化合物 A1、A8、A13 和 A14，然后合成 A1 (A2-A7) 和 A8 (A9-A12) 的其他类似物) 通过 IR、NMR、质量和元素技术进行表征。通过各种机制研究评估了这些化合物对 DU-145、MCF-7、HCT-15、HT-29 细胞系的体外抗增殖活性和细胞凋亡诱导潜力。与母体化合物和标准药物5-氟尿嘧啶相比，化合物A2、A9、A10表现出显着的细胞毒活性。化合物 A2 在大多数测试的细胞系中表现出优异的细胞毒性，IC50 值小于 1 µM。此外，化合物 A2 还诱导 DU-145 细胞凋亡，如 DAPI 染色、Annexin V-FITC 测定、ROS 生成和线粒体膜改变研究所示。上述研究描述了合成的化合物A2作为有效的抗癌剂，具有诱导前列腺癌细胞凋亡的能力。
• Synthesis and Fluorescence Properties of α,α′-Bis(substituted-benzylidene)cycloalkanones Catalyzed by 1-Methyl-3(2-(sulfooxy)ethyl)-1<i>H</i>-imidazol-3-ium Chloride
  作者：Yu Wan、Xiu-Mei Chen、Li-Ling Pang、Rui Ma、Cai-Hui Yue、Rui Yuan、Wei Lin、Wei Yin、Rong-Cheng Bo、Hui Wu

  DOI：10.1080/00397910903243781

  日期：2010.7.12

  α,α′-Bis(substituted-benzylidene)cycloalkanones were synthesized via a solvent-free cross-aldol condensation of aromatic aldehydes with cycloalkanones in the presence of a catalytic amount 1-methyl-3(2-(sulfooxy)ethyl)-1H-imidazol-3-ium chloride at room temperature with excellent yields. The screening for optical properties indicated that the size of cycloalkanone has an influence on the fluorescence

  在催化量的 1-甲基-3(2-(磺氧基)乙基)-1H 存在下，通过芳香醛与环烷酮的无溶剂交叉羟醛缩合反应合成了 α,α'-双（取代亚苄基）环烷酮-咪唑-3-氯化鎓在室温下以优异的收率。光学性质的筛选表明，环烷酮的大小对产物的荧光发射有影响。来自环己酮的产物比来自环戊酮的产物具有更强的荧光发射。
• Synthesis of Sulfonated Carbon Nanocage and Its Performance as Solid Acid Catalyst
  作者：Pei Lin、Baolin Li、Jiangtao Li、Huichun Wang、Xiaobing Bian、Xiaomei Wang

  DOI：10.1007/s10562-010-0526-6

  日期：2011.3

  A carbon nanocage material (CKT) was first successfully sulfonated by introducing sulfophenyl groups on the surface of pore channels through benzenesulfonic acid-containing aryl radical in situ generated from the reaction of 4-aminobenzenesulfonic acid and isoamyl nitrite in water. The sulfonated carbon nanocage material (S-CKT) was characterized by Fourier transform infrared spectroscopy, transmission electron microscopy, powder small-angle X-ray diffraction and nitrogen sorption measurements. The results showed that the S-CKT still possess the high specific surface area (787 m(2)/g) and uniform mesoporous (pore diameter 4.7 nm) structures, although the structure of S-CKT is slightly disorder, compared with its unsulfonated precursor. S-CKT, as a carbon-based solid acid catalyst, showed good catalytic performance and reusability in the cross-Aldol condensation of ketones with aromatic aldehydes under solvent-free condition.
• Substituted thiazoles V. Synthesis and antitumor activity of novel thiazolo[2,3-b]quinazoline and pyrido[4,3-d]thiazolo[3,2-a]pyrimidine analogues
  作者：Fatmah A.M. Al-Omary、Ghada S. Hassan、Shahenda M. El-Messery、Hussein I. El-Subbagh

  DOI：10.1016/j.ejmech.2011.10.023

  日期：2012.1

  A novel series of thiazolo[2,3-b]quinazoline (14-23, 26 and 27), and pyrido[4,3-d]thiazolo[3,2-a] pyrimidine (34-43, 45 and 46) analogues were designed and synthesized. The obtained compounds were evaluated for their in-vitro antitumor activity at the National Cancer Institute (NCI) 60 cell lines panel assay. Compounds 22, 38, 40 and 41 showed remarkable broad-spectrum antitumor activity. Compounds 22 and 38 are almost nine fold more active than 5-FU, with GI(50), TGI, and LC50 values of 2.5, >100, >100; and 2.4, 9.1, 36.2 mu M, respectively; while 40 and 41 are almost seven fold more active than 5-FU, with GI(50), TGI, and LC50 values of 2.9, 12.4, 46.6 and 3.0, 16.3, 54.0 mu M, respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.