α,α'-bis-veratrylidenecyclohexanone | 18977-33-8

• 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: α,α'-bis-veratrylidenecyclohexanone
• 英文别名: 2,6-bis-(3,4-dimethoxy-benzylidene)-cyclohexanone；2,6-bis(3,4-dimethoxybenzylidene)cyclohexanone；2,6-diveratrylidene-cyclohexanone；2,6-Diveratryliden-cyclohexanon；2,6-Bis[(3,4-dimethoxyphenyl)methylidene]cyclohexan-1-one
• CAS: 18977-33-8
• 化学式: C₂₄H₂₆O₅
• mdl: MFCD00121530
• 分子量: 394.467
• InChiKey: YOTDZZKBJHGVNA-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157°C

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：

  α,α'-bis-veratrylidenecyclohexanone 在 sodium acetate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 乙酸酐 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 2-(4-chloro-benzylidene)-9-(3,4-dimethoxy-benzylidene)-5-(3,4-dimethoxy-phenyl)-6,7,8,9-tetrahydro-5H-thiazolo[2,3-b]quinazolin-3-one
  参考文献：
  名称：

  合成具有抗炎和止痛作用的新型偶氮恶嗪

  摘要：

  从嘧啶-2-硫酮开始，获得了一组新的稠合三唑，噻唑和噻嗪。在光谱信息和元素分析的基础上，确定了所有新产品的机理和结构。预先准备了所有制备的化合物的镇痛和抗炎活性。结果表明，所有检查的样品均显示出有效的活性。此外，还研究了结构与活动之间的关系。

  DOI：

  10.1002/jhet.2746
• 作为产物：
  描述：

  2-(3,4-dimethoxyphenylmethylene)cyclohexanone 、 3,4-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以66.33%的产率得到α,α'-bis-veratrylidenecyclohexanone
  参考文献：
  名称：

  Asymmetrical meta-methoxylated diarylpentanoids: Rational design, synthesis and anti-cancer evaluation in-vitro

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2018.08.039

文献信息

• 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 biological evaluation of new curcumin analogues as antioxidant and antitumor agents: Molecular modeling study
  作者：Said M. Bayomi、Hassan A. El-Kashef、Mahmoud B. El-Ashmawy、Magda N.A. Nasr、Magda A. El-Sherbeny、Naglaa I. Abdel-Aziz、Magda A.-A. El-Sayed、Ghada M. Suddek、Shahenda M. El-Messery、Mariam A. Ghaly

  DOI：10.1016/j.ejmech.2015.07.014

  日期：2015.8

  New curcumin analogues have been synthesized and their antioxidant activities were investigated by measuring their free radical scavenging capacities. The in vitro and in vivo antitumor activities of the synthesized compounds on Ehrlich ascites carcinoma (EAC) cell line were evaluated. 4-(4-Chlorophenyl)-2-(5-ethyl-7-(4-methoxybenzylidene)-3-(4-methoxyphenyl)-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3-c]

  已经合成了新的姜黄素类似物，并通过测量其清除自由基的能力来研究其抗氧化活性。在体外和体内对艾氏腹水癌的合成的化合物的抗肿瘤活性（EAC）细胞系进行了评价。4-（4-氯苯基）-2-（5-乙基-7-（4-甲氧基亚苄基）-3-（4-甲氧基苯基）-3,3a，4,5,6,7-六氢-2 H-吡唑并[ 4,3- ç ]吡啶-2-基）噻唑7H表明在兼具优异的抗肿瘤活性在体外和体内研究中更重要的是试验化合物和参考药，顺铂。进行了不同的分子建模研究，其中化合物的对接端粒酶活性位点7h提示其可以通过抑制端粒酶发挥其抗肿瘤作用。
• 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。
• Homology Modeling of NAD ⁺ -Dependent DNA Ligase of the Wolbachia Endosymbiont of Brugia malayi and Its Drug Target Potential Using Dispiro-Cycloalkanones
  作者：Nidhi Shrivastava、Jeetendra K. Nag、Jyoti Pandey、Rama Pati Tripathi、Priyanka Shah、Mohammad Imran Siddiqi、Shailja Misra-Bhattacharya

  DOI：10.1128/aac.03449-14

  日期：2015.7

  Lymphatic filarial nematodes maintain a mutualistic relationship with the endosymbiont Wolbachia . Depletion of Wolbachia produces profound defects in nematode development, fertility, and viability and thus has great promise as a novel approach for treating filarial diseases. NAD ⁺ -dependent DNA ligase is an essential enzyme of DNA replication, repair, and recombination. Therefore, in the present study, the antifilarial drug target potential of the NAD ⁺ -dependent DNA ligase of the Wolbachia symbiont of Brugia malayi ( w Bm-LigA) was investigated using dispiro-cycloalkanone compounds. Dispiro-cycloalkanone specifically inhibited the nick-closing and cohesive-end ligation activities of the enzyme without inhibiting human or T4 DNA ligase. The mode of inhibition was competitive with the NAD ⁺ cofactor. Docking studies also revealed the interaction of these compounds with the active site of the target enzyme. The adverse effects of these inhibitors were observed on adult and microfilarial stages of B. malayi in vitro , and the most active compounds were further monitored in vivo in jirds and mastomys rodent models. Compounds 1, 2, and 5 had severe adverse effects in vitro on the motility of both adult worms and microfilariae at low concentrations. Compound 2 was the best inhibitor, with the lowest 50% inhibitory concentration (IC ₅₀ ) (1.02 μM), followed by compound 5 (IC ₅₀ , 2.3 μM) and compound 1 (IC ₅₀ , 2.9 μM). These compounds also exhibited the same adverse effect on adult worms and microfilariae in vivo ( P < 0.05). These compounds also tremendously reduced the wolbachial load, as evident by quantitative real-time PCR ( P < 0.05). w Bm-LigA thus shows great promise as an antifilarial drug target, and dispiro-cycloalkanone compounds show great promise as antifilarial lead candidates.

  摘要 淋巴丝虫与内生共生体 Wolbachia .消耗 沃尔巴克氏体 会造成线虫发育、繁殖力和存活率的严重缺陷，因此有望成为治疗丝虫病的一种新方法。NAD + -依赖性 DNA 连接酶是 DNA 复制、修复和重组过程中必不可少的酶。因此，在本研究中，NAD + 依赖性 DNA 连接酶的抗丝虫药物靶标潜力是研究的重点。 + -依赖性 DNA 连接酶的抗丝虫药物靶点潜力。 沃尔巴克氏体 共生体的 马来布鲁氏菌 ( w Bm-LigA）的二螺环烷酮化合物进行了研究。二螺环烷酮能特异性地抑制该酶的缺口闭合和内聚端连接活性，而对人类或 T4 DNA 连接酶没有抑制作用。其抑制方式与 NAD + 辅助因子的竞争性抑制。对接研究还揭示了这些化合物与目标酶活性位点的相互作用。这些抑制剂对成虫和微丝蚴阶段的 马拉伊蚊 体外 的不利影响，并进一步监测了最具活性的化合物 体内 在鸟类和啮齿动物模型中进行了进一步监测。化合物 1、2 和 5 在体外具有严重的不良影响 在体外 在低浓度下对成虫和微丝蚴的蠕动都有严重的不利影响。化合物 2 是最好的抑制剂，其最低的 50% 抑制浓度（IC 50 ）（1.02 μM），其次是化合物 5（IC 50 为 2.3 μM）和化合物 1（IC 50 为 2.9 μM）。这些化合物对成虫和微丝蚴也表现出同样的不利影响 在体内 ( P 0.05）。通过实时定量 PCR 检测，这些化合物还大大减少了狼尾蚴的数量 ( P 0.05）。 w 因此，Bm-LigA 很有希望成为抗丝虫药物的靶点，二螺环烷酮化合物也很有希望成为抗丝虫的候选先导化合物。
• Practical Enantioselective Synthesis of Chiroptical Polymers of Intrinsic Microporosity with Circular Polarized Luminescence
  作者：Xinbo Wang、Hao Guo、Cong Yu、Yuanju Jing、Zhaobin Han、Xiaohua Ma、Chenchen Yang、Minghua Liu、Dong Zhai、Daoyuan Zheng、Yupeng Pan、Xiaoju Li、Kuiling Ding

  DOI：10.1021/acs.macromol.1c01462

  日期：2021.12.14

  processability. However, PIMs with chiral backbones are quite limited, which undoubtedly hinders their applications in many areas such as chiral separation and optoelectronics. Herein, the catalytic enantioselective synthesis of a novel cyclohexyl-fused spirobiindane-based chiral PIM is described. This novel polymer exhibits high intrinsic microporosity (SBET = 796 m2 g–1), solubility, and good film formability

  具有固有微孔率 (PIM) 的聚合物由于其高微孔率和良好的溶液加工性，最近在气体分离、传感器、催化剂等领域受到越来越多的关注。然而，具有手性骨架的PIMs非常有限，这无疑阻碍了它们在手性分离和光电子等许多领域的应用。在此，描述了一种新型环己基稠合螺联茚基手性 PIM 的催化对映选择性合成。这种新型聚合物具有很高的固有微孔率 ( S BET = 796 m 2 g –1)，溶解性好，成膜性好。圆二色性证实了其扭曲弯曲结构的宏观手性。更有趣的是，首次在 PIM 中观察到圆偏振发光 (CPL)；此外，据我们所知，这是第一种非共轭多孔 CPL 聚合物，为探索 PIM 材料的新研究领域打开了大门，并为 CPL 聚合物设计提供了新的指导。