2,6-bis-(4-dimethylamino-2-nitrobenzylidene)cyclohexanone | 1613452-89-3

• 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-(4-dimethylamino-2-nitrobenzylidene)cyclohexanone
• 英文别名: 2,6-bis(4-dimethylamino-2-nitrobenzylidene)cyclohexanone
• CAS: 1613452-89-3
• 化学式: C₂₄H₂₆N₄O₅
• 分子量: 450.494
• InChiKey: RMXPZACONAODOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109.83
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,6-bis-(4-dimethylamino-2-nitrobenzylidene)cyclohexanone 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 以50%的产率得到2,6-bis(4-dimethylamino-2-nitrobenzylidene)cyclohexanone oxime
  参考文献：
  名称：

  姜黄素类似物肟作为潜在抗癌剂的合成及机理研究。

  摘要：

  使用天然或合成药物进行化学预防可降低癌症的发生率。除合成化合物外，许多天然产物还显示出在体内抑制癌变的潜力。在这项研究中，以α，β-不饱和羰基为基础的抗癌化合物被用作合成新肟类似物的原料。使用七种不同的人类癌细胞系进行的抗增殖分析发现提供了结构活性关系的清晰图片。肟类似物即7a和8a对细胞系显示出强大的抗增殖活性。研究了化合物对EGFR-TK激酶，微管蛋白聚合和BRAFV600E的作用机理。另外，还研究了化合物在逆转癌细胞产生的外排介导的抗性中的功效。

  DOI：

  10.1111/cbdd.12964
• 作为产物：
  描述：

  环己酮 、 4-二甲氨基-2-硝基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2,6-bis-(4-dimethylamino-2-nitrobenzylidene)cyclohexanone
  参考文献：
  名称：

  姜黄素类似物肟作为潜在抗癌剂的合成及机理研究。

  摘要：

  使用天然或合成药物进行化学预防可降低癌症的发生率。除合成化合物外，许多天然产物还显示出在体内抑制癌变的潜力。在这项研究中，以α，β-不饱和羰基为基础的抗癌化合物被用作合成新肟类似物的原料。使用七种不同的人类癌细胞系进行的抗增殖分析发现提供了结构活性关系的清晰图片。肟类似物即7a和8a对细胞系显示出强大的抗增殖活性。研究了化合物对EGFR-TK激酶，微管蛋白聚合和BRAFV600E的作用机理。另外，还研究了化合物在逆转癌细胞产生的外排介导的抗性中的功效。

  DOI：

  10.1111/cbdd.12964

文献信息

• Inhibitory effects of α, β-unsaturated carbonyl-based compounds and their pyrazoline derivatives on the phagocytosis of human neutrophils
  作者：Laiba Arshad、Ibrahim Jantan、Syed Nasir Abbas Bukhari、Shajarahtunnur Jamil

  DOI：10.1007/s00044-018-2163-3

  日期：2018.5

  neutrophils with the highest suppressive effects exhibited by compound 21 at 37.4%. Compounds 4, 11, 13, 14, 24, 25, 27, 33, and 34 significantly suppressed ROS generation by PMNs and WBC. Compounds with N-methyl 4-piperidone and 4-piperidone linkers (4, 13, 14, 23, 24) and 2-pyrazoline-1-carboxamide and 2-pyrazoline-1-carbothioamide derivatives showed strong inhibition on chemotactic and phagocytic activities

  研究了一系列α，β-不饱和羰基化合物（姜黄素类似物和查尔酮衍生物）及其吡唑啉衍生物对人嗜中性白细胞吞噬作用的体外抑制作用。通过使用24孔细胞评估了化合物对人全血细胞（WBC）和分离的人多形核中性粒细胞（PMN）趋化迁移，CD11a / 18表达，吞噬活性和活性氧（ROS）产生的影响迁移测定试剂盒，流式细胞仪，Phagotest测定试剂盒和基于鲁米诺/荧光素的化学发光测定。化合物4，5，6，13，23，33，39，和41表现出对PMN趋化作用的强抑制活性，IC 50值为0.22-1.68 µM，远低于布洛芬和姜黄素（IC 50值为11.02和5.0 µM）。所有化合物显示细胞粘附分子表达的低或中等抑制除化合物15，而化合物4，5，8，和21在100，图25，和6.25微克/毫升表明调理细菌吞噬的强烈抑制由具有最高抑制嗜中性粒细胞化合物21显示出37.4％的效果。化合物4，11，13，14，2
• Biological Activity and Molecular Docking Studies of Curcumin-Related α,β-Unsaturated Carbonyl-Based Synthetic Compounds as Anticancer Agents and Mushroom Tyrosinase Inhibitors
  作者：Syed Nasir Abbas Bukhari、Ibrahim Jantan、Oya Unsal Tan、Muhammad Sher、M. Naeem-ul-Hassan、Hua-Li Qin

  DOI：10.1021/jf501145b

  日期：2014.6.18

  Hyperpigmentation in human skin and enzymatic browning in fruits, which are caused by tyrosinase enzyme, are not desirable. Investigations in the discovery of tyrosinase enzyme inhibitors and search for improved cytotoxic agents continue to be an important line in drug discovery and development. In present work, a new series of 30 compounds bearing α,β-unsaturated carbonyl moiety was designed and synthesized following curcumin as model. All compounds were evaluated for their effects on human cancer cell lines and mushroom tyrosinase enzyme. Moreover, the structure-activity relationships of these compounds are also explained. Molecular modeling studies of these new compounds were carried out to explore interactions with tyrosinase enzyme. Synthetic curcumin-like compounds (2a-b) were identified as potent anticancer agents with 81-82% cytotoxicity. Five of these newly synthesized compounds (1a, 8a-b, 10a-b) emerged to be the potent inhibitors of mushroom tyrosinase, providing further insight into designing compounds useful in fields of food, health, and agriculture.
• Pharmacological evaluation and docking studies of α,β-unsaturated carbonyl based synthetic compounds as inhibitors of secretory phospholipase A2, cyclooxygenases, lipoxygenase and proinflammatory cytokines
  作者：Syed Nasir Abbas Bukhari、Gianluigi Lauro、Ibrahim Jantan、Giuseppe Bifulco、Muhammad Wahab Amjad

  DOI：10.1016/j.bmc.2014.05.052

  日期：2014.8

  Arachidonic acid and its metabolites have generated high level of interest among researchers due to their vital role in inflammation. The inhibition of enzymes involved in arachidonic acid metabolism has been considered as synergistic anti-inflammatory effect. A series of novel alpha,beta-unsaturated carbonyl based compounds were synthesized and evaluated for their inhibitory activity on secretory phospholipase A(2) (sPLA(2)), cyclooxygenases (COX), soybean lipoxygenase (LOX) in addition to proinflammatory cytokines comprising IL-6 and TNF-alpha. Six alpha,beta-unsaturated carbonyl based compounds (2, 3, 4, 12, 13 and 14) exhibited strong inhibition of sPLA(2) activity, with IC50 values in the range of 2.19-8.76 mu M. Nine compounds 1-4 and 10-14 displayed inhibition of COX-1 with IC50 values ranging from 0.37 to 1.77 mu M (lower than that of reference compound), whereas compounds 2, 10, 13 and 14 strongly inhibited the COX-2. The compounds 10-14 exhibited strong inhibitory activity against LOX enzyme. All compounds were evaluated for the inhibitory activities against LPS-induced TNF-alpha and IL-6 release in the macrophages. On the basis of screening results, five active compounds 3,4, 12,13 and 14 were found strong inhibitors of TNF-alpha and IL-6 release in a dose-dependent manner. Molecular docking experiments were performed to clarify the molecular aspects of the observed COX and LOX inhibitory activities of the investigated compounds. Present findings increases the possibility that these alpha,beta-unsaturated carbonyl based compounds might serve as beneficial starting point for the design and development of improved anti-inflammatory agents. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of α, β-unsaturated carbonyl based compounds as acetylcholinesterase and butyrylcholinesterase inhibitors: Characterization, molecular modeling, QSAR studies and effect against amyloid β-induced cytotoxicity
  作者：Syed Nasir Abbas Bukhari、Ibrahim Jantan、Vijay H. Masand、Devidas T. Mahajan、Muhammad Sher、M. Naeem-ul-Hassan、Muhammad Wahab Amjad

  DOI：10.1016/j.ejmech.2014.06.034

  日期：2014.8

  A series of novel carbonyl compounds was synthesized by a simple, eco-friendly and efficient method. These compounds were screened for anti-oxidant activity, in vitro cytotoxicity and for inhibitory activity for acetylcholinesterase and butyrylcholinesterase. The effect of these compounds against amyloid β-induced cytotoxicity was also investigated. Among them, compound 14 exhibited strong free radical scavenging activity (18.39 μM) while six compounds (1, 3, 4, 13, 14, and 19) were found to be the most protective against Aβ-induced neuronal cell death in PC12 cells. Compounds 4 and 14, containing N-methyl-4-piperidone linker, showed high acetylcholinesterase inhibitory activity as compared to reference drug donepezil. Molecular docking and QSAR (Quantitative Structure-Activity Relationship) studies were also carried out to determine the structural features that are responsible for the acetylcholinesterase and butyrylcholinesterase inhibitory activity.
• Synthesis and mechanistic studies of curcumin analog-based oximes as potential anticancer agents
  作者：Hua-Li Qin、Jing Leng、Bahaa G. M. Youssif、Muhammad Wahab Amjad、Maria Abdul Ghafoor Raja、Muhammad Ajaz Hussain、Zahid Hussain、Syeda Naveed Kazmi、Syed Nasir Abbas Bukhari

  DOI：10.1111/cbdd.12964

  日期：2017.9

  this study, α, β-unsaturated carbonyl-based anticancer compounds were used as starting materials to synthesize new oxime analogs. The findings from the antiproliferative assay using seven different human cancer cell lines provided a clear picture of structure-activity relationship. The oxime analogs namely 7a and 8a showed strong antiproliferative activity against the cell lines. The mechanistic effects

  使用天然或合成药物进行化学预防可降低癌症的发生率。除合成化合物外，许多天然产物还显示出在体内抑制癌变的潜力。在这项研究中，以α，β-不饱和羰基为基础的抗癌化合物被用作合成新肟类似物的原料。使用七种不同的人类癌细胞系进行的抗增殖分析发现提供了结构活性关系的清晰图片。肟类似物即7a和8a对细胞系显示出强大的抗增殖活性。研究了化合物对EGFR-TK激酶，微管蛋白聚合和BRAFV600E的作用机理。另外，还研究了化合物在逆转癌细胞产生的外排介导的抗性中的功效。