(E)-1-(4-methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one | 1003377-77-2

• 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-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-3-(2,4,5-trimethoxyphenyl)-1-(4-methoxyphenyl)propenone；(E)-1-(4-methoxyphenyl)-3-(2,4,5-methoxyphenyl)prop-2-en-1-one；(2E)-1-(4-methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1003377-77-2
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: XWQOUAAFTLPOSW-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以63%的产率得到(E)-1-(4-hydroxyphenyl)-3-(2,4,5-trihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  变形链球菌葡糖基转移酶和生物膜的羟查尔酮抑制剂作为潜在的抗龋剂

  摘要：

  变形链球菌由于其形成顽强生物膜的强大能力，已被认为是龋齿发生和发展的主要病因。该疾病的理想疗法将旨在选择性地抑制生物膜形成过程，同时保留口腔的天然细菌菌群。多项研究证明了黄酮醇对变形链球菌生物膜的功效，并通过其对变形链球菌的作用提出了作用机制。葡萄糖基转移酶（Gtfs）。这些酶将蔗糖代谢为水不溶性和可溶性葡聚糖，这是龋齿发病机理的重要指标。大量研究表明，黄酮醇和多酚可以抑制毫摩尔浓度的Gtf和生物膜的形成。我们在变形链球菌生物膜测定中筛选了14种羟基黄酮，它们是黄酮醇的合成前体。这些化合物中的几种在低摩尔浓度下已成为生物膜抑制剂。在环A上含有3-OH基团的Chalcones表现出对生物膜抑制的选择性。此外，我们合成了铅化合物的6个其他类似物，并评估了它们对变形链球菌的潜在活性和选择性。生物膜。从这些研究中鉴定出的最具活性的化合物，对生物膜的IC 50值为44μM，对生长的MIC 50值为468μM，显示出对生物膜的选择性抑制>

  DOI：

  10.1016/j.bmcl.2016.06.033
• 作为产物：
  描述：

  顺式-2,4,5-三甲氧基-1-丙烯基苯 在 potassium permanganate 、 碳酸氢钠 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-1-(4-methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structure–activity relationship

  摘要：

  2,4,5-Trimethoxy chalcones and analogues were synthesized from asaronaldehyde derived from beta-asarone. These novel compounds when tested against three human tumour cell lines (MCF-7, SW-982 and HeLa) using MTT assay, revealed that chalcones possessing electron donor groups in para position to carbonyl moiety of phenyl ring A, showed better inhibitory activity (2, 3, 4, 6, 7, 10, 17). When evaluated for antioxidant activities, compound 15 exhibited better free radical scavenging property in DPPH assay while compounds 2, 3, 5, 7, 9, 10, 11, 16, and 18 showed significant NO scavenging activity. All compounds exhibited very good phenyl hydrazine induced haemolysis of erythrocytes in phenylhydrazine assay. Structure activity relationship (SAR) study using in-silico analysis matched well with in-vitro tumour cell inhibitory activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.018

文献信息

• Synthesis and Cytotoxic Evaluation of Alkoxylated Chalcones
  作者：Xiao-Guang Bai、Chang-Liang Xu、Shuang-Shuang Zhao、Hong-Wei He、Yu-Cheng Wang、Ju-Xian Wang

  DOI：10.3390/molecules191117256

  日期：——

  A series of chalcones a1–20 bearing a 4-OMe groups on the A-ring were initially synthesized and their anticancer activities towards HepG2 cells evaluated. Subsequently, a series of chalcones b1–42 bearing methoxy groups at the 2' and 6'-positions of the B-ring were synthesized and their anticancer activities towards five human cancer cell lines (HepG2, HeLa, MCF-7, A549 and SW1990) and two non-tumoral human cell lines evaluated. The results showed that six compounds (b6, b8, b11, b16, b18, b22, b23 and b29) displayed promising activities, with compounds b22 and b29 in particular showing higher levels of activity than etoposide against all five cancer cell lines. Compound b29 showed a promising SI value compared with both HMLE and L02 (2.1–6.5 fold in HMLE and > 33 > 103.1 fold in L02, respectively).

  一系列在A环上带有4-OMe基团查尔酮a1-20被合成，并评估了它们对HepG2细胞的抗癌活性。随后，合成了一系列在B环的2'和6'-位置带有甲氧基的查尔酮b1-42，并评估了它们对五种人癌细胞系（HepG2、HeLa、MCF-7、A549和SW1990）和两种非瘤人细胞系的抗癌活性。结果显示，六个化合物（b6、b8、b11、b16、b18、b22、b23和b29）显示出有望的活性，特别是化合物b22和b29在所有五种癌细胞系中显示出比依托泊苷更高的活性水平。与HMLE和L02相比，化合物b29显示出有希望的SI值（分别是HMLE的2.1-6.5倍，L02的>103.1倍）。
• Hansch’s analysis application to chalcone synthesis by Claisen–Schmidt reaction based in DFT methodology
  作者：Marco Mellado、Alejandro Madrid、Úrsula Martínez、Jaime Mella、Cristian O. Salas、Mauricio Cuellar

  DOI：10.1007/s11696-017-0316-3

  日期：2018.3

  Chalcones are bioactive compounds obtained from either natural sources or synthetic procedures and widely used due to their several biological properties. The most common experimental methodology in obtaining these compounds is Claisen–Schmidt reaction, which is a particular type of aldolic condensation. In this work, we have synthesized 23 chalcones and by density functional theory (DFT) calculation

  查耳酮是从天然来源或合成方法获得的生物活性化合物，由于其多种生物学特性而被广泛使用。获得这些化合物最常见的实验方法是克莱森-施密特反应，这是一种特殊的醛醇缩合反应。在这项工作中，我们合成了23个查耳酮，并通过密度泛函理论（DFT）计算，我们研究了几种苯甲醛的反应性差异及其对该反应产率的影响。在分子轨道描述符的基础上，基于Hansch的分析获得了两个定量结构-反应性关系（QSRR）模型。这项研究的结果表明，对于大多数苯甲醛（23种化合物中的15种），它们的反应性与LUMO能量和全球亲电指数相关（ω）值，这是在克莱森－施密特凝聚机理（亲核加成）的第一步中确定的。同样，对于最小的苯甲醛类，它们的反应性与它们的HOMO和ΔL  -  H（LUMO-HOMO）能量有关，这是在机理的第二步（反式消除）中确定的。这是基于DFT方法分析查尔酮合成产率的QSRR模型的第一份报告。
• ANTI-INVASIVE COMPOUNDS
  申请人：Universiteit Gent

  公开号：US20150011620A1

  公开（公告）日：2015-01-08

  The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.

  本发明涉及抗侵袭化合物领域，以及预测该类化合物抗侵袭活性的方法，以及它们在预防和/或治疗与不受欢迎的细胞侵袭相关的疾病中的用途；特别是，本发明涉及抗侵袭的类似香豆素化合物领域。
• Synthesis, Characterization and Antimicrobial Activities of Chalcones and Their Post Transformation to Pyrazole Derivatives
  作者：D. Ramyashree、K.R. Raghavendra、A. Dileep Kumar、C.B. Vagish、K. Ajay Kumar

  DOI：10.14233/ajchem.2017.20561

  日期：——

  An efficient procedure for the synthesis of trisubstituted pyrazoles was developed. Claisen-Schmidt condensation of 2,4,5-trimethoxybenzaldehyde and substituted acetophenone in the presence of aqueous alkaline bases produced chalcones. The cyclocondensation reaction of chalcones and phenyl hydrazine hydrochloride catalyzed by an acid produced trisubstituted pyrazolines in good yields. The synthesized new compounds were characterized by spectral studies and elemental analysis and some of the intermediate chalcones by single crystal X-ray diffraction studies. The compounds were screened in vitro for their antimicrobial susceptibilities against different bacteria and fungi species.

  开发了一种合成三取代吡唑的高效工艺。在含水碱性条件下，2,4,5-三甲氧基苯甲醛与取代苯乙酮进行克莱森-施密特缩合反应，生成查耳酮。在酸催化下，查耳酮与苯肼盐酸盐发生环化缩合反应，以良好产率生成三取代吡唑啉。通过光谱研究和元素分析对合成的新化合物进行了表征，部分中间体查耳酮通过单晶X射线衍射研究进行了鉴定。对这些化合物进行了体外抗菌活性筛选，测试了它们对不同细菌和真菌种类的抗菌敏感性。
• [EN] STREPTOCOCCUS MUTANS GLUCOSYL TRANSFERASE INHIBITORS FOR DENTAL CARIES THERAPY<br/>[FR] INHIBITEURS DE GLUCOSYLE TRANSFÉRASE DE STREPTOCOCCUS MUTANS POUR LA THÉRAPIE DES CARIES DENTAIRES
  申请人：UAB RESEARCH FOUNDATION

  公开号：WO2019195430A1

  公开（公告）日：2019-10-10

  The present invention is related to the inhibition of the formation of Streptococci biofilms through the inhibition of glucosyl transferase (Gtf). Compounds, compositions and methods for inhibiting Streptococcus biofilm formation, as well as for preventing, inhibiting and/or treating the formation of dental caries, and methods of identifying compounds that prevent, inhibit and/or treat the formation of dental caries are provided.

  本发明涉及通过抑制葡萄糖基转移酶(Gtf)来抑制链球菌生物膜形成的方法。提供了用于抑制链球菌生物膜形成的化合物、组合物和方法，以及用于预防、抑制和/或治疗龋齿形成的方法，以及用于识别能够预防、抑制和/或治疗龋齿形成的化合物的方法。