(E)-1-(4-methoxyphenyl)-3-(4-(methylthio)phenyl)prop-2-en-1-one

• 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: (E)-1-(4-methoxyphenyl)-3-(4-(methylthio)phenyl)prop-2-en-1-one
• 英文别名: (E)-1-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₆O₂S
• 分子量: 284.379
• InChiKey: ZGIOCWWESCNBFZ-LFYBBSHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(甲基巯基)苯甲醛 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-1-(4-methoxyphenyl)-3-(4-(methylthio)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Chalcones and Bis-Chalcones Analogs as DPPH and ABTS Radical Scavengers

  摘要：

  背景：许多合成支架物以及天然产物被确定为有效的抗氧化剂。本研究涉及对不同取代、具有药用特性的化合物类别“查尔酮和双查尔酮”进行抗氧化潜力评估。 方法：对一系列合成查尔酮1-13和双查尔酮14-18进行体外自由基清除活性测试。 结果：所有分子1-18在IC50范围内显示出明显的2,2-二苯基-1-苯基-亚硝基肼（DPPH）和2,2'-联苯二(3-乙基苯并噻唑啉-6-磺酸)（ABTS）自由基清除潜力，分别为0.58 ± 0.14 - 1.72 ± 0.03和0.49 ± 0.3 - 1.48 ± 0.06 μM。抗坏血酸（DPPH和ABTS的IC50分别为0.5 ± 0.1和0.46 ± 0.17 μM）被用作标准自由基清除剂。 结论：结构活性关系（SAR）显示了各种基团，包括-SMe和-OMe在清除活性中的积极参与。

  DOI：

  10.2174/1570180817999201001155032

文献信息

• Alkene Synthesis by Photo‐Wolff‐Kischner Reaction of Sulfur Ylides and <i>N</i> ‐Tosylhydrazones
  作者：Pan‐Pan Gao、Dong‐Mei Yan、Ming‐Hang Bi、Min Jiang、Wen‐Jing Xiao、Jia‐Rong Chen

  DOI：10.1002/chem.202102671

  日期：2021.10.13

  A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity

  首次开发了硫叶立德和 N-甲苯磺酰腙的可见光驱动和室温光沃尔夫-基施纳反应，以提供烯烃合成的模块化途径。60 多个实例证明了高官能团耐受性和广泛的底物范围。产品中的 E- 和 Z- 烯烃立体化学都可以以优异的立体选择性进行控制。一系列机理研究支持该反应应该通过自由基 - 负离子交叉途径进行，具体涉及将光生硫叶立德自由基阳离子添加到 N-甲苯磺酰腙形成碳负离子和随后的沃尔夫-基施纳过程。
• CHALCONE DERIVATIVE COMPOUNDS
  申请人：NIPPON OIL AND FATS COMPANY, LIMITED

  公开号：EP0328669A1

  公开（公告）日：1989-08-23

  Chalcone derivative compounds represented by general formula (I) or (II), wherein R₁ and R₂ each represents a ha­logen atom, a hydroxy group, an amino group, a dimethylamino group, a nitro group, a cyano group, a phenyl group, an acetyl group, an alkyl group containing 1 to 18 carbon atoms or an alkyloxy group containing 1 to 22 carbon atoms, n₁ and n₂ each represents an integer of 0 to 21, and m₁ and m₂ each represents an integer of 0 to 5.

  通式(I)或(II)代表的查耳酮衍生物化合物，其中 R₁ 和 R₂ 各自代表卤素原子、羟基、氨基、二甲基氨基、硝基、氰基、苯基、乙酰基、含 1 至 18 个碳原子的烷基或含 1 至 22 个碳原子的烷氧基，n₁ 和 n₂ 各自代表整数、乙酰基、含 1 至 18 个碳原子的烷基或含 1 至 22 个碳原子的烷氧基，n₁ 和 n₂ 各自代表 0 至 21 的整数，m₁ 和 m₂ 各自代表 0 至 5 的整数。
• Chalcones and bis-chalcones: As potential α-amylase inhibitors; synthesis, in vitro screening, and molecular modelling studies
  作者：Adebayo Tajudeen Bale、Khalid Mohammed Khan、Uzma Salar、Sridevi Chigurupati、Tolulope Fasina、Farman Ali、Kanwal、Abdul Wadood、Muhammad Taha、Sitansu Sekhar Nanda、Mehreen Ghufran、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2018.05.003

  日期：2018.9

  Despite of a diverse range of biological activities associated with chalcones and bis-chalcones, they are still neglected by the medicinal chemist for their possible alpha-amylase inhibitory activity. So, the current study is based on the evaluation of this class for the identification of new leads as alpha-amylase inhibitors. For that purpose, a library of substituted chalcones 1-13 and bis-chalcones 14-18 were synthesized and characterized by spectroscopic techniques EI-MS and H-1 NMR. CHN analysis was carried out and found in agreement with the calculated values. All compounds were evaluated for in vitro alpha-amylase inhibitory activity and demonstrated good activities in the range of IC50 = 1.25 +/- 1.05-2.40 +/- 0.09 mu M as compared to the standard acarbose (IC50 = 1.04 +/- 0.3 mu M). Limited structure-activity relationship (SAR) was established by considering the effect of different groups attached to aryl rings on varying inhibitory activity. SMe group in chalcones and OMe group in bis-chalcones were found more influential on the activity than other groups. However, in order to predict the involvement of different groups in the binding interactions with the active site of alpha-amylase enzyme, in silico studies were also conducted.
• Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives
  作者：P.M. Sivakumar、S. Prabu Seenivasan、Vanaja Kumar、Mukesh Doble

  DOI：10.1016/j.bmcl.2006.12.112

  日期：2007.3

  In order to develop relatively small molecules as antimycobacterial agents, twenty-five chalcones were synthesized, their activity was evaluated, and quantitative structure-activity relationship (QSAR) was developed. The synthesis was based on the Claisen-Schimdt scheme and the resultant compounds were tested for antitubercular activity by luciferase reporter phage (LRP) assay. Compound C-24 was found to be the most active (similar to 99%) in this series based on the percentage reduction in Relative Light Units at both 50 and 100 mu g/ml levels, followed by compound C-21. Four compounds at the 50 mu g/ml and eight compounds at the 100 mu g/ml showed activity above 90% level. QSAR model was developed between activity and spatial, topological, and ADME descriptors for the 50 mu g/ml data. The statistical measures such as r, r(2), q(2), and F values obtained for the training set were in acceptable range and hence this relationship was used for the test set. The predictive ability of the model is satisfactory (q(2) = 0.56) and it can be used for designing similar group of compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• Chalcones and Bis-Chalcones Analogs as DPPH and ABTS Radical Scavengers
  作者：Adebayo Tajudeen Bale、Uzma Salar、Khalid Mohammed Khan、Sridevi Chigurupati、Tolulope Fasina、Farman Ali、Muhammad Ali、Sitansu Sekhar Nanda、Muhammad Taha、Shahnaz Perveen

  DOI：10.2174/1570180817999201001155032

  日期：2021.3

  A number of synthetic scaffolds, along with natural products, have been identified as potent antioxidants. The present study deals with the evaluation of varyingly substituted, medicinally distinct class of compounds “chalcones and bis-chalcones” for their antioxidant potential.

  In vitro radical scavenging activities were performed on a series of synthetic chalcones 1- 13 and bis-chalcones 14-18.

  All molecules 1-18 revealed a pronounced 2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2ʹ- azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radicals scavenging potential in the ranges of IC_50s = 0.58 ± 0.14 - 1.72 ± 0.03 and 0.49 ± 0.3 - 1.48 ± 0.06 μM, respectively. Ascorbic acid (IC_50s = 0.5 ± 0.1 and 0.46 ± 0.17 μM for DPPH and ABTS, respectively) was used as a standard radical scavenger.

  Structure-activity relationship (SAR) revealed an active participation of various groups, including -SMe and -OMe in scavenging activity.

  背景：许多合成支架物以及天然产物被确定为有效的抗氧化剂。本研究涉及对不同取代、具有药用特性的化合物类别“查尔酮和双查尔酮”进行抗氧化潜力评估。 方法：对一系列合成查尔酮1-13和双查尔酮14-18进行体外自由基清除活性测试。 结果：所有分子1-18在IC50范围内显示出明显的2,2-二苯基-1-苯基-亚硝基肼（DPPH）和2,2'-联苯二(3-乙基苯并噻唑啉-6-磺酸)（ABTS）自由基清除潜力，分别为0.58 ± 0.14 - 1.72 ± 0.03和0.49 ± 0.3 - 1.48 ± 0.06 μM。抗坏血酸（DPPH和ABTS的IC50分别为0.5 ± 0.1和0.46 ± 0.17 μM）被用作标准自由基清除剂。 结论：结构活性关系（SAR）显示了各种基团，包括-SMe和-OMe在清除活性中的积极参与。

表征谱图