(E)-3-(4-(methylthio)phenyl)-1-(p-tolyl)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)-3-(4-(methylthio)phenyl)-1-(p-tolyl)prop-2-en-1-one
• 英文别名: trans-4'-Methyl-4-(methylthio)chalcone；(E)-1-(4-methylphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₆OS
• 分子量: 268.379
• InChiKey: OZJHMGGPZMUIJN-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 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：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-(methylthio)phenyl)-1-(p-tolyl)prop-2-en-1-one 、 (Z)-3-(4-chlorophenyl)-5-ethylidene-4-methylene-1,3-oxazolidin-2-one 以 甲苯 为溶剂， 反应 24.0h， 以76%的产率得到
  参考文献：
  名称：

  通过的高度选择性狄尔斯-阿尔德环加成的4,5,6,7- tetrahydrobenzoxazol -2-酮的合成外-恶唑烷-2-酮与查耳酮二烯

  摘要：

  本文报道了新颖的4,5,6,7-四氢苯并恶唑-2-酮的合成。它们是通过N-取代的外-恶唑烷-2-酮二烯与查耳酮或双查耳酮作为亲二烯体的高度区域选择性和立体选择性Diels-Alder环加成反应而以中等至良好的产率获得的。

  DOI：

  10.1016/j.tetlet.2019.04.027
• 作为产物：
  描述：

  对甲基苯乙酮 、 4-(甲基巯基)苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以69%的产率得到(E)-3-(4-(methylthio)phenyl)-1-(p-tolyl)prop-2-en-1-one
  参考文献：
  名称：

  通过的高度选择性狄尔斯-阿尔德环加成的4,5,6,7- tetrahydrobenzoxazol -2-酮的合成外-恶唑烷-2-酮与查耳酮二烯

  摘要：

  本文报道了新颖的4,5,6,7-四氢苯并恶唑-2-酮的合成。它们是通过N-取代的外-恶唑烷-2-酮二烯与查耳酮或双查耳酮作为亲二烯体的高度区域选择性和立体选择性Diels-Alder环加成反应而以中等至良好的产率获得的。

  DOI：

  10.1016/j.tetlet.2019.04.027

文献信息

• 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。
• 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.
• Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure–activity relationship analysis and regulation of apoptotic proteins
  作者：Chun Wai Mai、Marzieh Yaeghoobi、Noorsaadah Abd-Rahman、Yew Beng Kang、Mallikarjuna Rao Pichika

  DOI：10.1016/j.ejmech.2014.03.002

  日期：2014.4

  In the present study, a series of 46 chalcones were synthesised and evaluated for antiproliferative activities against the human TRAIL-resistant breast (MCF-7, MDA-MB-231), cervical (HeLa), ovarian (Caov-3), lung (A549), liver (HepG2), colorectal (HT-29), nasopharyngeal (CNE-1), erythromyeloblastoid (K-562) and T-Iymphoblastoid (CEM-SS) cancer cells. The chalcone 38 containing an amino (-NH2) group on ring A was the most potent and selective against cancer cells. The effects of the chalcone 38 on regulation of 43 apoptosis-related markers in HT-29 cells were determined. The results showed that 20 apoptotic markers (Bad, Bax, BcI-2, Bcl-w, Bid, Bim, CD40, Fas, HSP27, IGF-1, IGFBP-4, IGFBP-5, Livin, p21, Survivin, 5TNE-R2, TRAIL-R2, XIAP, caspase-3 and caspase-8) were either up regulated or down regulated. (C) 2014 Elsevier Masson SAS.All rights reserved.
• 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.

表征谱图