(E)-3-(4-(benzyloxy)phenyl)-1-(p-tolyl)prop-2-en-1-one | 86711-45-7

• 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-(p-tolyl)prop-2-en-1-one
• 英文别名: 4-benzyloxy-4'-methyl-trans-chalcone；4-Benzyloxy-4'-methyl-trans-chalkon；(2E)-3-[4-(Benzyloxy)phenyl]-1-(4-methylphenyl)prop-2-en-1-one；(E)-1-(4-methylphenyl)-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 86711-45-7
• 化学式: C₂₃H₂₀O₂
• 分子量: 328.411
• InChiKey: NRODJPGJMUQZBB-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 对甲基苯乙酮 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-3-(4-(benzyloxy)phenyl)-1-(p-tolyl)prop-2-en-1-one
  参考文献：
  名称：

  与姜黄素有关的芳族烯酮的合成及生物学评价。

  摘要：

  姜黄素是从香料姜黄中分离得到的天然产物，已显示出广泛的药理活性，包括某些抗癌特性。它已被明确地证明是在体外和体内血管生成的有效抑制剂。使用姜黄素作为抗血管生成类似物设计的先导化合物，已经合成了一系列利用取代的查尔酮骨架的结构相关化合物，并通过已建立的SVR细胞增殖测定法进行了测试。结果产生了范围广泛的化合物，这些化合物等于或超过姜黄素体外抑制内皮细胞生长的能力。由于它们的商业可获得性和相当简单的合成制备方法，这些低分子量化合物是开发未来血管生成抑制剂的诱人线索。

  DOI：

  10.1016/j.bmc.2005.03.054

文献信息

• Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia‐derived cells: Role of PKCβ
  作者：Emanuela Corsini、Giorgio Facchetti、Sara Esposito、Ambra Maddalon、Isabella Rimoldi、Michael S. Christodoulou

  DOI：10.1002/ardp.202000062

  日期：2020.7

  series of 20 chalcone derivatives was synthesized, and their antiproliferative activity was tested against the human T cell acute lymphoblastic leukemia‐derived cell line, CCRF‐CEM. On the basis of the structural features of the most active compounds, a new library of chalcone derivatives, according to the structure–activity relationship design, was synthesized, and their antiproliferative activity was

  在这项研究中，合成了一系列 20 种查耳酮衍生物，并测试了它们对人 T 细胞急性淋巴细胞白血病衍生细胞系 CCRF-CEM 的抗增殖活性。在活性最强化合物的结构特征的基础上，根据构效关系设计合成了一个新的查尔酮衍生物库，并测试了它们对同一癌细胞系的抗增殖活性。此外，这些衍生物中的四种（化合物 3、4、8、28）基于较低的 IC50 值（在 6.1 和 8.9 μM 之间），被选择用于进一步研究 RACK1（活化 C 激酶的受体）的蛋白质表达的调节)、蛋白激酶 C (PKC)α 和 PKCβ，以及它们在细胞周期水平上的作用。细胞周期分析表明所有四种化合物均在 G0/G1 期出现阻滞，S 期细胞百分比在统计学上显着降低，没有细胞凋亡迹象（亚 G0/G1 期）。化合物 4 和 8 显示出 PKCα 表达的统计学显着降低和 PKCβ 的增加，这与 PKCβ 的抗增殖作用的证明一起，如通过用选择性 PKCβ
• 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 and its analogs as agents for the inhibition of angiogenesis and related disease states
  申请人：Bowen Phillip J.

  公开号：US20050148599A1

  公开（公告）日：2005-07-07

  The present invention relates to chalcone and chalcone derivatives and analogs which are useful as angiogenesis inhibitors. The present compounds, which are inexpensive to synthesize, exhibit unexpectedly good activity as angiogenesis inhibitors. The present invention also relates to the use of chalcone and its analogs as antitumor/anticancer agents and to treat a number of conditions or disease states in which angiogenesis is a factor, incluidng angiongenic skin diseases such as psoriasis, acne, rosacea, warts, eczema, hemangiomas, lymphangiogenesis, among numerous others, as well as chronic inflammatory disease such as arthritis.

  本发明涉及查尔酮和查尔酮衍生物及类似物，其可用作抗血管生成抑制剂。这些化合物成本低廉且表现出意外的良好抗血管生成活性。本发明还涉及使用查尔酮及其类似物作为抗肿瘤/抗癌剂以及治疗许多条件或疾病状态，其中血管生成是一个因素，包括血管生成性皮肤病如银屑病、痤疮、酒渣鼻、疣、湿疹、血管瘤、淋巴管生成等等，以及慢性炎症性疾病如关节炎。
• 213. Chalkones: reactivity of phenyl p-benzyloxystyryl ketones
  作者：S. N. Rao、T. S. Wheeler

  DOI：10.1039/jr9390001004

  日期：——
• 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.