4-dimethylaminobenzal-4'-chloroacetophenone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-dimethylaminobenzal-4'-chloroacetophenone
• 英文别名: 4'-chloro-4-dimethylaminochalcone；1-(4-chlorophenyl)-3-(4-dimethylaminopheny)-2-propen-1-one；1-(4-Chlorophenyl)-3-(4-dimethylaminophenyl)-1-oxoprop-2-ene；1-(4-chlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
• 化学式: C₁₇H₁₆ClNO
• mdl: MFCD00018706
• 分子量: 285.773
• InChiKey: WUXTYVHXWDGPIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-dimethylaminobenzal-4'-chloroacetophenone 在 溴 作用下， 以 氯仿 为溶剂， 生成 2,3-dibromo-1-(4-chloro-phenyl)-3-(4-dimethylamino-phenyl)-propan-1-one
  参考文献：
  名称：

  Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines

  摘要：

  2,4-Dichloro-5-fluorophenyl containing 7-arylidenetriazolothiadiazines were obtained by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with 2,3-dibromo-1,3-diarylpropan-1-ones, and also by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with alpha-bromopropenones in the presence of a base. The structure of the 7-arylidenetriazolothiadiazines was confirmed by an alternative synthesis. A plausible mechanism for the formation of 7-arylidenetriazolothiadiazines is proposed. All newly synthesized compounds were screened for their analgesic and antimicrobial activities. Compounds bearing 4-chlorophenyl or 3,4-methylenedioxyphenyl moieties at position 7 of the arylidenetriazolothiadiazines showed excellent analgesic activity. Arylidenetriazolothiadiazines carrying a phenyl, 4-chlorophenyl, 4-methylphenyl, 3,4-dimethoxyphenyl, and 2,4-dichlorophenyl moieties at position 7 showed excellent antibacterial and antifungal activities.

  DOI：

  10.1007/s00706-007-0797-9
• 作为产物：
  描述：

  2,3-dibromo-1-(4-chloro-phenyl)-3-(4-dimethylamino-phenyl)-propan-1-one 在 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 4-dimethylaminobenzal-4'-chloroacetophenone
  参考文献：
  名称：

  Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines

  摘要：

  2,4-Dichloro-5-fluorophenyl containing 7-arylidenetriazolothiadiazines were obtained by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with 2,3-dibromo-1,3-diarylpropan-1-ones, and also by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with alpha-bromopropenones in the presence of a base. The structure of the 7-arylidenetriazolothiadiazines was confirmed by an alternative synthesis. A plausible mechanism for the formation of 7-arylidenetriazolothiadiazines is proposed. All newly synthesized compounds were screened for their analgesic and antimicrobial activities. Compounds bearing 4-chlorophenyl or 3,4-methylenedioxyphenyl moieties at position 7 of the arylidenetriazolothiadiazines showed excellent analgesic activity. Arylidenetriazolothiadiazines carrying a phenyl, 4-chlorophenyl, 4-methylphenyl, 3,4-dimethoxyphenyl, and 2,4-dichlorophenyl moieties at position 7 showed excellent antibacterial and antifungal activities.

  DOI：

  10.1007/s00706-007-0797-9

文献信息

• Novel benzothiazole based sulfonylureas/sulfonylthioureas: design, synthesis and evaluation of their antidiabetic potential
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Sameena Bano、Yakub Ali、Abhijeet Dhulap、Parwez Alam、M. A. Q. Pasha

  DOI：10.1039/c5nj03589a

  日期：——

  Twenty-eight benzothiazole based sulfonylureas/sulfonylthioureas were synthesized and were found to be effective against diabetes as PPAR-γ agonists.

  合成了 28 种基于苯并噻唑的磺酰脲类/磺酰硫脲类，发现它们作为 PPAR-γ 激动剂对糖尿病有效。
• Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Sameena Bano、Abhijeet Dhulap、Yakub Ali、Syed Nazreen、Saqlain Haider

  DOI：10.1016/j.bmc.2014.09.028

  日期：2014.11

  aims at the synthesis of pyrazolines bearing benzothiazole and their evaluation as anti-inflammatory agents. The synthesized compounds were evaluated for their anti-inflammatory potential using carrageenan induced paw edema model. Two compounds 5a and 5d alleviated inflammation more than the standard drug celecoxib. Eight compounds 5b, 5c, 5e, 5g, 5h, 6b, 6e and 6f showed anti-inflammatory activity comparable

  本研究旨在合成带有苯并噻唑的吡唑啉及其作为抗炎药的评价。使用角叉菜胶诱导的爪水肿模型评价合成的化合物的抗炎潜力。两种化合物5a和5d比标准药物塞来昔布更能减轻炎症。八个化合物5b，5c，5e，5g，5h，6b，6e和6f显示出与塞来昔布相当的抗炎活性。为了理解作用方式，进行了COX-2酶测定和TNF-α测定。评估所有活性化合物的细胞毒性。对未发现有细胞毒性的活性化合物进行了致溃疡风险评估。在十种活性化合物中，最终发现两种化合物（5d和6f）是最有效的抗炎药，可抑制COX-2酶活性和TNF-α的产生，而不会产生细胞毒性或致溃疡性。
• Pyrazoline analogs as potential anticancer agents and their apoptosis, molecular docking, MD simulation, DNA binding and antioxidant studies
  作者：Manish Rana、Rizwan Arif、Faez Iqbal Khan、Vikas Maurya、Raja Singh、Md Imam Faizan、Shama Yasmeen、Sajad Hussain Dar、Raquib Alam、Ankita Sahu、Tanveer Ahmad、Rahisuddin

  DOI：10.1016/j.bioorg.2021.104665

  日期：2021.3

  18 µM). The anticancer activity of potent derivatives (3b and 3d) against A549 cancer cell line was further confirmed by flow cytometry based approach. DNA binding interactions of the pyrazoline derivatives 3b and 3d have been carried out with calf thymus DNA (Ct-DNA) using absorption, fluorescence and viscosity measurements, circular dichroism and cyclic voltammetry. Antioxidant potential of N-formyl

  N-甲酰基吡唑啉衍生物（3a-3l）是通过迈克尔加成反应通过查耳酮与水合肼在甲酸存在下的环化反应设计和合成的。N-甲酰基吡唑啉衍生物的结构解析通过各种光谱技术进行，如1 H、13 C NMR、FT-IR、紫外-可见光谱、质谱和元素分析。吡唑啉衍生物 ( 3a-3l ) 对人肺癌 ( A549)、纤维肉瘤细胞系 ( HT1080)和人原代正常肺细胞 ( HFL-1) 的抗癌活性进行了评估通过 MTT 测定。抗癌活性的结果表明，有效的类似物3b和3d对A549（IC 50  = 12.47 ± 1.08 和 14.46 ± 2.76 µM）和HT1080（IC 50  = 11.40 ± 0.66 和 23.73 ± 13）表现出有希望的活性，但对毒性低HFL-1（IC 50  = 116.47 ± 43.38 和 152.36 ± 22.18 µM）。通过基于流式细胞术的方法进一步证实了有效衍生物（3b和3d）对
• Characterization of the Fluorescence Properties of 4-Dialkylaminochalcones and Investigation of the Cytotoxic Mechanism of Chalcones
  作者：Bo Zhou、Peixin Jiang、Junxuan Lu、Chengguo Xing

  DOI：10.1002/ardp.201500434

  日期：2016.7

  structure–activity relationship in their cellular cytotoxicity, leading to the identification of structurally similar cytotoxic and non‐cytotoxic fluorescent chalcones as chemical probes. Confocal microscopy results revealed the co‐localization of the cytotoxic probe C8 and tubulin in cells, supporting tubulin as the direct cellular target responsible for the cytotoxicity of chalcones.

  了解负责查耳酮的各种生物活动的机制，特别是直接的细胞靶点，是一个未解决的挑战。在这里，我们制备了一系列荧光查耳酮衍生物作为化学探针，用于其机理研究。通过系统的物理化学表征，我们探索了它们阐明查耳酮细胞毒性作用模式的潜力。发现查耳酮的荧光对结构和环境因素高度敏感。在结构上，B 环上的 4-二烷基氨基、A 环取代基的合适电子性质以及查耳酮核心结构的平面构象对于最佳荧光至关重要。影响荧光的环境因素包括溶剂极性、pH、以及查耳酮与蛋白质和洗涤剂的相互作用。发现 18 种查耳酮在 DMSO 中的荧光亮度大于 6000 M-1 cm-1。然而，水显着地淬灭了荧光，尽管它可以在 BSA 或去污剂的存在下部分恢复。正如预期的那样，这些荧光查耳酮在其细胞细胞毒性方面表现出明显的构效关系，从而导致鉴定出结构相似的细胞毒性和非细胞毒性荧光查耳酮作为化学探针。共聚焦显微镜结果揭示了细胞毒性探针 C8 和微管蛋白在
• Design, Synthesis and Evaluation of Chalcone Derivatives as Anti- Inflammatory, Antioxidant and Antiulcer Agents
  作者：Alka N. Choudhary、Arun Kumar、Vijay Juy

  DOI：10.2174/157018012800389368

  日期：2012.4.26

  In the present study, a series of chalcone derivatives were designed based on QSAR analysis. The designed compounds were synthesized by Claisen Schmidt condensation and evaluated for anti-inflammatory, antioxidant and antiulcer activities. The results of the best 2D & 3D QSAR models suggested that by introducing electron releasing groups at R2 and introducing heteroatom with increasing bulkiness at R4 in the benzylideneacetophenone nucleus will increase the activity. The structures of the compounds were established by IR, 1H NMR and mass spectral analysis. All the compounds were evaluated for their anti-inflammatory (carrageenan-induced rat paw edema assay), antioxidant (inhibition of lipid peroxidation) and antiulcer activity (indomethacin-induced gastric damage). Of 10 compounds screened, compounds 1e and 1d exhibited promising anti-inflammatory activity with 68-70% inhibition at 100mg/kg , inhibition of lipid peroxidation with IC50 2.47 & 3.1 μg/ml respectively. The Compounds 1e, 1j and 1d exhibited good gastro protective action as indicated by their low ulcer score. Overall, 1e was obtained as lead compound with promising anti-inflammatory, antioxidant and antiulcer activities.

  在本研究中，基于QSAR分析设计了一系列查尔酮衍生物。通过克莱森-施密特缩合合成了所设计的化合物，并评估了它们的抗炎、抗氧化和抗溃疡活性。最佳的2D和3D QSAR模型的结果表明，通过在R2引入电子给体基团，以及在R4引入增量体的杂原子，可以提高活性。通过红外光谱、1H NMR和质谱分析确定了化合物的结构。所有化合物都经过了抗炎（卡拉胶诱导的大鼠足肿胀实验）、抗氧化（抑制脂质过氧化）和抗溃疡活性（吲哚美辛诱导的胃损伤）的评估。在筛选的10个化合物中，化合物1e和1d在100mg/kg剂量下表现出68-70%的抗炎活性，脂质过氧化抑制的IC50分别为2.47和3.1 μg/ml。化合物1e、1j和1d表现出良好的胃保护作用，其溃疡评分较低。总体而言，1e被确定为具有良好抗炎、抗氧化和抗溃疡活性的领先化合物。