1-(4-chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one | 941607-53-0

• 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: 1-(4-chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: 2,4,5-trimethoxy-4′-chlorochalcone；2,4,5TMCC
• CAS: 941607-53-0
• 化学式: C₁₈H₁₇ClO₄
• 分子量: 332.784
• InChiKey: ZZEIAZLHMGCAHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one 在 甲酸 作用下， 以 甲醇 、 水 为溶剂， 以82%的产率得到1-(4-chlorophenyl)-3-(2,4,5-trimethoxyphenyl)propan-1-one
  参考文献：
  名称：

  甲氧基化查耳酮作为抗疟药的结构-活性关系的再研究：2,4,5-三甲氧基取代的模式作为衍生自大量可用的天然β-细辛酮的潜在候选化合物的合成和评估

  摘要：

  我们已经使用基于荧光的SYBR Green分析方法检测了一系列甲氧基化查耳酮（A –CH CH–CO– B）对恶性疟原虫（3D7株）的抗疟结构与活性的关系。我们的研究表明，环A上的释放电子的甲氧基和环B上的吸电子基团提高了抗疟药的效力，而这些基团的位置互换导致其降低。特别地，在环2,4,5-三甲氧基取代模式甲提供一种很容易从可大量获得的天然衍生的强效的类似物β细辛醚丰富菖蒲油。细胞毒性评估表明，活性最高的化合物27（IC 50：1.8μM）和26（IC 50：2μM）也是相对无毒的。此外，化合物12对P的耐氯喹Dd2菌株显示出优异的抗性指数1.1 。恶性肿瘤。

  DOI：

  10.1016/j.ejmech.2010.08.049
• 作为产物：
  描述：

  顺式-2,4,5-三甲氧基-1-丙烯基苯 在 重铬酸吡啶 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.33h， 生成 1-(4-chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Tandem allylic oxidation–condensation/esterification catalyzed by silica gel: an expeditious approach towards antimalarial diaryldienones and enones from natural methoxylated phenylpropenes

  摘要：

  开发了一种新的单锅法策略，利用丰富的甲氧基化苯丙烯类化合物，通过烯丙位氧化-缩合或烯丙位氧化-酯化序列，直接转化为相应的二烯酮（1,5-二芳基-2,4-戊二烯-1-酮）和烯酮（查耳酮和肉桂酸酯）。对上述合成的二芳基二烯酮和烯酮进行的初步抗疟活性研究表明，它们是开发新型经济抗疟药物的有希望的先导候选物。特别是，两个烯酮（12b和13b）的活性（IC50分别为4.0和3.4微摩尔）优于已知的天然抗疟化合物licochalcone（IC50=4.1微摩尔）。

  DOI：

  10.1039/c1ob05293d

文献信息

• An experimental and theoretical study on a novel donor-π-acceptor bridge type 2, 4, 5-trimethoxy-4′-chlorochalcone for optoelectronic applications: A dual approach
  作者：Mohd. Shkir、P.S. Patil、M. Arora、S. AlFaify、H. Algarni

  DOI：10.1016/j.saa.2016.09.022

  日期：2017.2

  ochalcone (2,4,5TMCC) through experimental and quantum chemical studies. The Claisen–Schmidt condensation reaction mechanism was applied to synthesize the 2,4,5TMCC compound and its single crystal was grown by a slow evaporation solution growth (low cost) technique. The crystal structure was confirmed by powder X-ray diffraction analysis. The robust vibrational study has been done using FT-IR and FT-Raman

  本文的目的是通过实验和研究来研究和分析有机D-π-A型新型非线性光学材料2、4、5-三甲氧基-4'-氯查耳酮（2,4,5TMCC）的各种关键参数。量子化学研究。应用克莱森-施密特缩合反应机理合成2,4,5TMCC化合​​物，并通过缓慢蒸发溶液生长（低成本）技术生长其单晶。通过粉末X射线衍射分析确认晶体结构。使用FT-IR和FT-Raman光谱进行了鲁棒的振动研究，并讨论了其NLO活性。还进行了因素组分析。记录光吸收光谱并且计算出带隙为2.8eV。在光致发光光谱中 观察到在〜540 nm处有很强的发射带，这表明所生长的晶体可用于绿色有机发光二极管和激光应用。为了获得2,4,5TMCC的稳定基态分子几何结构，使用6-31G *基集在不同理论水平上应用了计算技术。计算出的几何参数和振动谱与实验结果吻合良好。为了探测标题化合物的光学性质，应用了时变密度泛函理论。在B3LYP / 6-31G *理论水平下计算，在〜398
• Synthesis of Unusually Substituted 2,4,5-Trimethoxy 3,5-Diaryl Isoxazoles from Natural Precursor: Antimicrobial and Anticancer Activities
  作者：M.V. Ravindra、S. Suvarna、C.S. Ananda Kumar

  DOI：10.14233/ajchem.2024.31015

  日期：——

  In this work, 2,4,5-trimethoxy substituted 3,5-diaryl isoxazoles were synthesized via their chalcone intermediates and evaluated for antimicrobial and anticancer activities. The natural precursor 2,4,5-trimethoxy benzaldehyde (asaronaldehyde) was obtained from oxidation of β-asarone (Acorus calamus oil) and then reacted with substituted acetophenones via Claisen-Schmidt condensation yielded 2,4,5-trimethoxy substituted chalcones. These chalcones on further treatment with hydroxylamine in presence of sodium acetate and acetic acid cyclizes to give the corresponding 3,5-diaryl isoxazoles yields ranging from 65-80%. Structures were confirmed by IR, GC-MS, 1H NMR and 13C NMR. Synthesized compounds were screened for their antimicrobial activity against bacteria and fungi. The para-substituted isoxazoles (5b, 5c and 5d) exhibited good activity against Gram-negative (Escherichia coli) and (Pseudomonas aeruginosa) and Gram-positive (Bacillus subtilis) and Bacillus licheniformis bacteria and fungi (Phytophthora capsici, Sclerotirum rolfsii, Aspergillus niger and Alternaria alternate). Further, these novel analogues were evaluated for their in vitro anticancer activity against three human tumor cell lines (MCF-7, SW-982 and HeLa) using MTT assay. The anticancer results revealed that phenyl ring at C-3 position bearing electron donor groups in the para-position and 2,4,5-trimethoxy substitutent of the phenyl ring at C-5 position isoxazole showed better inhibitory activity (5b, 5c and 5d). Among synthesized isoxazoles due to the hyper conjugative effect, 2,4,5-trimethoxy 3,5-diaryl isoxazole (5g) having 3-triflouromethyl substitution showed good antimicrobial and higher inhibitory IC50 values 8.56 ± 0.32, 12.16 ± 0.86 and 10.16 ± 0.68 μg/mL (p < 0.05) respectively, when compared to natural precursor β-asarone.
• Reinvestigation of structure–activity relationship of methoxylated chalcones as antimalarials: Synthesis and evaluation of 2,4,5-trimethoxy substituted patterns as lead candidates derived from abundantly available natural β-asarone
  作者：Rakesh Kumar、Dinesh Mohanakrishnan、Abhishek Sharma、Naveen Kumar Kaushik、Kalpana Kalia、Arun Kumar Sinha、Dinkar Sahal

  DOI：10.1016/j.ejmech.2010.08.049

  日期：2010.11

  causes a decrease. In particular, 2,4,5-trimethoxy substitution pattern at ring A provided potent analogues which were easily derived from abundantly available natural β-asarone rich Acorus calamus oil. Cytotoxic evaluation indicated that the most active compounds 27 (IC50: 1.8 μM) and 26 (IC50: 2 μM) were also relatively non-toxic. Furthermore, compound 12 showed excellent resistance index of 1.1 against

  我们已经使用基于荧光的SYBR Green分析方法检测了一系列甲氧基化查耳酮（A –CH CH–CO– B）对恶性疟原虫（3D7株）的抗疟结构与活性的关系。我们的研究表明，环A上的释放电子的甲氧基和环B上的吸电子基团提高了抗疟药的效力，而这些基团的位置互换导致其降低。特别地，在环2,4,5-三甲氧基取代模式甲提供一种很容易从可大量获得的天然衍生的强效的类似物β细辛醚丰富菖蒲油。细胞毒性评估表明，活性最高的化合物27（IC 50：1.8μM）和26（IC 50：2μM）也是相对无毒的。此外，化合物12对P的耐氯喹Dd2菌株显示出优异的抗性指数1.1 。恶性肿瘤。
• Tandem allylic oxidation–condensation/esterification catalyzed by silica gel: an expeditious approach towards antimalarial diaryldienones and enones from natural methoxylated phenylpropenes
  作者：Abhishek Sharma、Naina Sharma、Amit Shard、Rakesh Kumar、Dinesh Mohanakrishnan、Saima、Arun K. Sinha、Dinkar Sahal

  DOI：10.1039/c1ob05293d

  日期：——

  A new one-pot strategy has been developed, wherein abundantly available methoxylated phenylpropenes are directly transformed into corresponding dienones (1,5-diarylpenta-2,4-dien-1-ones) and enones (chalcones and cinnamic esters) via allylic oxidation–condensation or allylic oxidation–esterification sequences. Preliminary antimalarial activity studies of the above synthesized diaryldienones and enones against Plasmodium falciparum (Pf3D7) have shown them to be promising lead candidates for developing newer and economical antimalarial agents. In particular, two enones (12b and 13b) were found to possess comparatively better activity (IC50 = 4.0 and 3.4 μM, respectively) than licochalcone (IC50 = 4.1 μM), a well known natural antimalarial compound.

  开发了一种新的单锅法策略，利用丰富的甲氧基化苯丙烯类化合物，通过烯丙位氧化-缩合或烯丙位氧化-酯化序列，直接转化为相应的二烯酮（1,5-二芳基-2,4-戊二烯-1-酮）和烯酮（查耳酮和肉桂酸酯）。对上述合成的二芳基二烯酮和烯酮进行的初步抗疟活性研究表明，它们是开发新型经济抗疟药物的有希望的先导候选物。特别是，两个烯酮（12b和13b）的活性（IC50分别为4.0和3.4微摩尔）优于已知的天然抗疟化合物licochalcone（IC50=4.1微摩尔）。