(E)-3-(4-(benzyloxy)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one | 1152162-36-1

• 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-(benzyloxy)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-3-[4-(Benzyloxy)phenyl]-1-(4-methoxyphenyl)prop-2-en-1-one；(E)-1-(4-methoxyphenyl)-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 1152162-36-1
• 化学式: C₂₃H₂₀O₃
• 分子量: 344.41
• InChiKey: TWYBNKWJRLRNCS-CXUHLZMHSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  537.1±50.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-(benzyloxy)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 (3E,5E)-6-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-1,1-diamino-2,3-diaza-1,3,5-hexatriene
  参考文献：
  名称：

  胍基的-ine互变异构现象：Az嗪互变异构体偏爱的证据

  摘要：

  鸟嘌呤nes已经很长时间了，在有机合成，药物化学和材料科学中有广泛的应用。然而，对其电子和结构性质的关注很少。对几种具有治疗意义的胍hydr进行的量子化学分析表明，它们均更倾向于互变异构态（约3-12 kcal / mol）。使用量子化学方法设计了一组简单且共轭的嗪，其互变异构体相对于嗪互变异构体的偏好度为3-8 kcal / mol。合成并分离了二十种新的中性状态的杂志。可变温度NMR研究表明，即使在较高温度下也没有trace互变异构体的痕迹，仍然存在嗪基互变异构体。

  DOI：

  10.1021/acs.joc.6b01258
• 作为产物：
  描述：

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

  胍基的-ine互变异构现象：Az嗪互变异构体偏爱的证据

  摘要：

  鸟嘌呤nes已经很长时间了，在有机合成，药物化学和材料科学中有广泛的应用。然而，对其电子和结构性质的关注很少。对几种具有治疗意义的胍hydr进行的量子化学分析表明，它们均更倾向于互变异构态（约3-12 kcal / mol）。使用量子化学方法设计了一组简单且共轭的嗪，其互变异构体相对于嗪互变异构体的偏好度为3-8 kcal / mol。合成并分离了二十种新的中性状态的杂志。可变温度NMR研究表明，即使在较高温度下也没有trace互变异构体的痕迹，仍然存在嗪基互变异构体。

  DOI：

  10.1021/acs.joc.6b01258

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。
• Orchestrating a β-Hydride Elimination Pathway in Palladium(II)-Catalyzed Arylation/Alkenylation of Cyclopropanols Using Organoboron Reagents
  作者：Thangeswaran Ramar、Murugaiah A. M. Subbaiah、Andivelu Ilangovan

  DOI：10.1021/acs.joc.1c02735

  日期：2022.4.1

  scope of chemoselective β-hydride elimination in the context of arylation/alkenylation of homoenolates from cyclopropanol precursors using organoboronic reagents as transmetalation coupling partners was examined. The reaction optimization paradigm revealed a simple ligand-free Pd(II) catalytic system to be most efficient under open air conditions. The preparative scope, which was investigated with

  在使用有机硼试剂作为金属转移偶联剂对环丙醇前体的高烯醇化物进行芳基化/烯基化的情况下，化学选择性 β-氢化物消除的范围进行了研究。反应优化范式揭示了一个简单的无配体 Pd(II) 催化体系在露天条件下最有效。用 48 个例子研究了制备范围，支持该反应适用于广泛的可耐受各种官能团的底物，同时以 62-95% 的产率提供 β-取代的烯酮和二烯酮衍生物。
• 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: A Valid Scaffold for Monoamine Oxidases Inhibitors
  作者：Franco Chimenti、Rossella Fioravanti、Adriana Bolasco、Paola Chimenti、Daniela Secci、Francesca Rossi、Matilde Yáñez、Francisco Orallo、Francesco Ortuso、Stefano Alcaro

  DOI：10.1021/jm801590u

  日期：2009.5.14

  A large series of substituted chalcones have been synthesized and tested in vitro for their ability to inhibit human monoamine oxidases A and B (hMAO-A and hMAO-B). While all the compounds showed hMAO-B selective activity in the micro- and nanomolar ranges, the best results were obtained in the presence of chlorine and hydroxyl or methoxyl substituents. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAO-B, molecular modeling studies were carried out on new, high resolution, hMAO-B crystallographic structures. For the only compound that also showed activity against hMAO-A as well as low selectivity, the molecular modeling study was also performed on the hMAO-A crystallographic structure. The docking technique provided new insight on the inhibition mechanism and the rational drug design of more potent/selective hMAO inhibitors based on the chalcone scaffold.
• Azine-Hydrazone Tautomerism of Guanylhydrazones: Evidence for the Preference Toward the Azine Tautomer
  作者：Sumit S. Chourasiya、Deepika Kathuria、Sampada S. Nikam、Ashok Ramakrishnan、Sadhika Khullar、Sanjay K. Mandal、Asit K. Chakraborti、Prasad V. Bharatam

  DOI：10.1021/acs.joc.6b01258

  日期：2016.9.2

  using quantum chemical methods, whose tautomeric preference toward the azine tautomer is in the range of 3–8 kcal/mol. Twenty new azines were synthesized and isolated in their neutral state. Variable temperature NMR study suggests existence of the azine tautomer even at higher temperatures with no traces of the hydrazone tautomer. The crystal structures of two representative compounds confirmed that the

  鸟嘌呤nes已经很长时间了，在有机合成，药物化学和材料科学中有广泛的应用。然而，对其电子和结构性质的关注很少。对几种具有治疗意义的胍hydr进行的量子化学分析表明，它们均更倾向于互变异构态（约3-12 kcal / mol）。使用量子化学方法设计了一组简单且共轭的嗪，其互变异构体相对于嗪互变异构体的偏好度为3-8 kcal / mol。合成并分离了二十种新的中性状态的杂志。可变温度NMR研究表明，即使在较高温度下也没有trace互变异构体的痕迹，仍然存在嗪基互变异构体。