3-(2,4-dimethoxyphenyl)-1-(4-nitrophenyl)propenone | 30929-50-1

• 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: 3-(2,4-dimethoxyphenyl)-1-(4-nitrophenyl)propenone
• 英文别名: 3-(4-Nitro-phenyl)-1-(2,4-dimethoxy-phenyl)-propen-(1)-on-(3)；1-(2,4-Dimethoxy-phenyl)-3-(4-nitro-phenyl)-propenon-(3)；p-Nitrophenyl-β-(2,4-dimethoxyphenyl)-vinyl-keton；3-(2,4-Dimethoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one
• CAS: 30929-50-1；30929-51-2；18493-32-8
• 化学式: C₁₇H₁₅NO₅
• 分子量: 313.31
• InChiKey: RNKXHTDJQOJJNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2,4-dimethoxyphenyl)-1-(4-nitrophenyl)propenone 在 Au NCs/TiO₂ 、 双氧水 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到
  参考文献：
  名称：

  低共熔溶剂（Reline）和二氧化钛（Au-TiO2）负载的金纳米粒子作为合成某些取代苯基（取代-3-苯基环氧乙烷）甲酮对映选择性过氧化反应的新型催化剂

  摘要：

  背景：过氧化氢氧化剂具有环保功能，氧化后产生的唯一副产品就是水。遗憾的是，它对查耳酮和查耳酮类似物的氧化能力很低，因此，它通常与催化剂一起使用或转化为氢过氧化物，以提高其氧化能力。 研究目的本研究旨在研究环氧化化学。因此，采用不同的技术和催化剂，将过氧化氢作为环氧化的潜在氧化剂。 方法：使用过氧化氢/碳酸氢钠，研究了（reline）（由两摩尔氯化胆碱和一摩尔尿素制得）作为深共晶溶剂（DES）或氧化钛（Au-TiO2）上支持的金（Au）催化剂纳米颗粒（NPs）在几种程序条件下对查尔酮衍生物过氧化反应的有利影响，以生成新型环氧乙烷（I-VI）。 结果与讨论：使用过氧化氢/碳酸氢钠-（Reline）混合物的方法（B）获得了可接受的结果，与传统方法（A）的不到 86% 的过氧化率和 24 小时相比，该方法在短时间（4 小时）内获得了 87-90% 的过氧化率，而使用氧化钛（Au-TiO2）上支持的 Au NPs 的方法（C）则获得了 90-95% 的最佳产率和时间（约 2 小时），约为（Reline）混合物的一半。这种情况可能是由于金和氧化钛纳米颗粒对过氧化氢的活化程度高，以及反应混合物的粘度低。 结论查尔酮环氧化反应让化学家们相信，使用深共晶溶剂（Reline）和氧化钛纳米颗粒上的金支持催化这些反应是在各种氧化分支中非常重要的技术。

  DOI：

  10.21608/ejchem.2021.68511.3498
• 作为产物：
  描述：

  对硝基苯乙酮 、 2,4-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以95%的产率得到3-(2,4-dimethoxyphenyl)-1-(4-nitrophenyl)propenone
  参考文献：
  名称：

  Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents

  摘要：

  Chalcones have been identified as interesting compounds with cytotoxicity, anti-inflammatory and antioxidant properties. In the present study, simple methoxychalcones were synthesized by Claisen-Schmidt condensation reaction and evaluated for above biological activities. The structures of the compounds were established by IR, (1)H NMR and mass spectral analysis. The data revealed that compound 3s (99-100% at 10 mu M concentration) completely inhibit the selected five human cancer cell lines as compared to standard flavopiridol and gemcitabine (70-90% at 700 nM and 500 nM concentrations, respectively), followed by 3a, 3n, 3o, 3p, 3q, 3r. Among the tested compounds 3l, 3m, 3r, and 3s exhibited promising anti-inflammatory activity against TNF-alpha and IL-6 with 90-100% inhibition at 10 mu M concentration. DPPH free radical scavenging activity was given by the compounds 3o, 3n, 3l, 3r, 3m, 3a, 3p, 3c and 3s at 1 mM concentration. Overall, 3s was obtained as lead compound with promising anticancer, anti-inflammatory and antioxidant activities. Bioavailability of compounds were checked by in vitro cytotoxicity study and confirmed to be nontoxic. The structure activity relationship (SAR) and in silico drug relevant properties (HBDs, HBAs, PSA, c Log P, ionization potential, molecular weight, E(HOMO) and E(LUMO)) further confirmed that the compounds were potential candidates for future drug discovery study. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.066

文献信息

• Synthesis, antioxidant evaluation, and quantitative structure–activity relationship studies of chalcones
  作者：P. M. Sivakumar、P. K. Prabhakar、M. Doble

  DOI：10.1007/s00044-010-9342-1

  日期：2011.5

  Synthesis, antioxidant activity, and quantitative structure-activity relationship (QSAR) of 25 of chalcone derivatives is reported here. They were synthesized by Claisen-Schmidt reaction and were characterized by FTIR, NMR, and mass spectroscopy. Antioxidant activity is evaluated through four different methods namely, superoxide radical-scavenging, hydrogen peroxide scavenging, reducing power, and DPPH radical-scavenging assays. Generally, compounds with -SCH3 and -OCH3 in the para position of the A-ring and -OH in the B-ring were more active than others. In few cases some of the compounds were more active than ascorbic acid or butylated hydroxytoluene. QSAR was developed correlating the antioxidant activity with the structural features of the compounds and the predictive capability of the models was estimated using internal and external validation methods. All the predictions were within the 99% confidence level. Spatial, structural, and lipophilic properties of the compounds determine their antioxidant properties.