(2E)-3-(3,4,5-trimethoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one | 1347761-12-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-3-(3,4,5-trimethoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one
• 英文别名: (E)-1-(pyridin-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；1-(pyridine-2-yl)-3-(3,4,5-trimethoxyphenyl)-2-propene-1-one；1-(2-pyridyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；(2E)-1-(pyridin-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；(E)-1-pyridin-2-yl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1347761-12-9
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: BPHYOXFAYJPCCZ-BQYQJAHWSA-N

物化性质

• 熔点：
  161-162 °C(Solv: acetone (67-64-1); ethanol (64-17-5))
• 沸点：
  468.8±45.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-3-(3,4,5-trimethoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one 在 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-(3-(pyridin-2-yl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis and antiproliferative activity of some 3-(pyrid-2-yl)-pyrazolines

  摘要：

  报告了 11 种 3-(吡啶-2-基)-吡唑类化合物的合成及其在两种癌细胞系中的抗增殖活性。对先导化合物 8i 进行了 X 射线晶体学研究，并在 NCI 60 人类肿瘤细胞系中进行了筛选，结果显示出亚微摩级的活性。此外，还报告了细胞周期分析、体外微管蛋白测定和共聚焦显微镜，结果表明该先导化合物破坏了微管的形成。

  DOI：

  10.1039/c3md00077j
• 作为产物：
  描述：

  2-乙酰基吡啶 、 3,4,5-三甲氧基苯甲醛 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以51%的产率得到(2E)-3-(3,4,5-trimethoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Simple, Rapid and Reliable Preparation of [11C]-(+)-a-DTBZ of High Quality for Routine Applications

  摘要：

  [11C]-(+)-a-DTBZ已被用作人类纹状体中多巴胺能终端密度的标记物，并在胰腺的胰岛β细胞中表达。我们旨在建立一个完全自动化和简单的程序，以合成[11C]-(+)-a-DTBZ，以便进行常规应用。[11C]-(+)-a-DTBZ是从一种9-羟基前体在丙酮和氢氧化钾的条件下与[11C]-甲基三氟甲磺酸酯合成的，并通过使用Vac tC-18柱的固相提取进行纯化。基于[11C]-甲基三氟甲磺酸酯（已校正衰减）的放射化学产率为82.3% ± 3.6%，具有60 GBq/mmol的比放射活性。从轰击结束到产品释放进行质量控制的时间少于20分钟。

  DOI：

  10.3390/molecules17066697

文献信息

• Influence of trimethoxy-substituted positions on fluorescence of heteroaryl chalcone derivatives
  作者：Thitipone Suwunwong、Suchada Chantrapromma、Hoong-Kun Fun

  DOI：10.2478/s11696-011-0084-4

  日期：2011.1.1

  Three series of heteroaryl chalcones, (E)-1-(2-pyridyl)-3-(X)prop-2-en-1-one (Ia-Ic), (E)-1-(2-thienyl)-3-(X)prop-2-en-1-one (IIa-IIc), and (E)-1-(2-furyl)-3-(X)prop-2-en-1-one (IIIa-IIIc), where X = 2,4,5-trimethoxyphenyl (for series a), X = 2,4,6-trimethoxyphenyl (for series b), and X = 3,4,5-trimethoxyphenyl (for series c) were synthesised using basic catalysed aldol condensation and characterised using 1H NMR and FT-IR spectroscopies. Compound IIa was also characterised by single crystal X-ray analysis. The absorption and fluorescence emission spectra of these compounds revealed that the absorption and fluorescence depended on the heterocycle rings and trimethoxysubstituted phenyl rings linked to the enone system. The position of methoxy groups substantially affected the fluorescent properties. Compounds Ia-IIIa containing the 2,4,5-trimethoxyphenyl moiety exhibited the red-shift phenomenon and strong emission fluorescence.

  摘要：三系列杂环假苋菜素，(E)-1-(2-吡啶基)-3-(X)丙-2-烯-1-酮（Ia-Ic），(E)-1-(2-噻吩基)-3-(X)丙-2-烯-1-酮（IIa-IIc），以及(E)-1-(2-呋喃基)-3-(X)丙-2-烯-1-酮（IIIa-IIIc），其中X = 2,4,5-三甲氧基苯基（对于a系列），X = 2,4,6-三甲氧基苯基（对于b系列），以及X = 3,4,5-三甲氧基苯基（对于c系列）通过碱催化的Aldol缩合合成，并使用1H NMR和FT-IR光谱进行表征。化合物IIa还通过单晶X射线分析进行了表征。这些化合物的吸收和荧光发射光谱表明，吸收和荧光取决于杂环环和连接到烯酮系统的三甲氧基取代苯环。甲氧基基团的位置明显影响了荧光性质。含有2,4,5-三甲氧基苯基基团的化合物Ia-IIIa表现出红移现象和强发射荧光。
• Synthesis and Selective Cytotoxic Activities on Rhabdomyosarcoma and Noncancerous Cells of Some Heterocyclic Chalcones
  作者：Tuong-Ha Do、Dai-Minh Nguyen、Van-Dat Truong、Thi-Hong-Tuoi Do、Minh-Tri Le、Thanh-Quan Pham、Khac-Minh Thai、Thanh-Dao Tran

  DOI：10.3390/molecules21030329

  日期：——

  Notably, the introduction of three methoxy groups at positions 3, 4, 5 on ring B appears to be critical for cytotoxicity. The best compound, with potent and selective cytotoxicity (IC50 = 12.51 μM in comparison with the value 10.84 μM of paclitaxel), contains a phenothiazine moiety on ring A and a thiophene heterocycle on ring B. Most of the potential compounds only show weak cytoxicity on the noncancerous

  制备化学上多样化的杂环查耳酮并评估其细胞毒性，旨在提高效力和选择性。他们针对横纹肌肉瘤（RMS）和非癌细胞系（LLC-PK1）进行了测试。研究了杂芳基构型对环A和B的影响。评价了两个环上的杂环官能度，例如吩噻嗪，噻吩，呋喃和吡啶。值得注意的是，在环B的3、4、5位引入三个甲氧基对细胞毒性至关重要。最好的化合物具有强力和选择性的细胞毒性（紫杉醇值为10.84μM，IC50 = 12.51μM），在A环上含有吩噻嗪部分，在B环上含有噻吩杂环。大多数潜在化合物仅在C上表现出弱的细胞毒性。非癌细胞系LLC-PK1。
• Simple, Rapid and Reliable Preparation of [11C]-(+)-a-DTBZ of High Quality for Routine Applications
  作者：Jinming Zhang、Xiaojun Zhang、Yungang Li、Jiahe Tian

  DOI：10.3390/molecules17066697

  日期：——

  [11C]-(+)-a-DTBZ has been used as a marker of dopaminergic terminal densities in human striatum and expressed in islet beta cells in the pancreas. We aimed to establish a fully automated and simple procedure for the synthesis of [11C]-(+)-a-DTBZ for routine applications. [11C]-(+)-a-DTBZ was synthesized from a 9-hydroxy precursor in acetone and potassium hydroxide with [11C]-methyl triflate and was purified by solid phase extraction using a Vac tC-18 cartridge. Radiochemical yields based on [11C]-methyl triflate (corrected for decay) were 82.3% ± 3.6%, with a specific radioactivity of 60 GBq/mmol. Time elapsed was less than 20 min from end of bombardment to release of the product for quality control.

  [11C]-(+)-a-DTBZ已被用作人类纹状体中多巴胺能终端密度的标记物，并在胰腺的胰岛β细胞中表达。我们旨在建立一个完全自动化和简单的程序，以合成[11C]-(+)-a-DTBZ，以便进行常规应用。[11C]-(+)-a-DTBZ是从一种9-羟基前体在丙酮和氢氧化钾的条件下与[11C]-甲基三氟甲磺酸酯合成的，并通过使用Vac tC-18柱的固相提取进行纯化。基于[11C]-甲基三氟甲磺酸酯（已校正衰减）的放射化学产率为82.3% ± 3.6%，具有60 GBq/mmol的比放射活性。从轰击结束到产品释放进行质量控制的时间少于20分钟。
• Synthesis, physicochemical properties, antimicrobial and antioxidant studies of pyrazoline derivatives bearing a pyridyl moiety
  作者：Imtiyaz Hussain Lone、Khaliquz Zaman Khan、Bharat Inder Fozdar

  DOI：10.1007/s00044-013-0643-z

  日期：2014.1

  A series of new pyrazoline compounds bearing a pyridyl moiety (4a-i) were synthesized by condensing appropriate chalcones with hydrazine hydrate and tested for antimicrobial and antioxidant activities. According to in vitro antimicrobial activity against Bacillus subtilis, Staphylococcus epidermidis, Proteus vulgaris, Pseudomonas aeruginosa, Aspergillus niger and Penicillium chrysogenum and antioxidant activity by DPPH method, the compounds 4a, 4d, 4i and 4e, 4f, 4h showed maximum antimicrobial and antioxidant activities, respectively. Physiochemical properties and Lipinski's 'Rule of Five' analysis predicted higher intrinsic quality of the synthesized compounds and revealed that these compounds have good bioavailability and druglikeness properties.
• Chalcones bearing a 3,4,5-trimethoxyphenyl motif are capable of selectively inhibiting oncogenic K-Ras signaling
  作者：Sarah E. Kovar、Cody Fourman、Christine Kinstedt、Brandon Williams、Christopher Morris、Kwang-jin Cho、Daniel M. Ketcha

  DOI：10.1016/j.bmcl.2020.127144

  日期：2020.6

  Ras proteins are small GTPases which regulate cellular proliferation, differentiation, and apoptosis. Constitutively active mutant Ras are expressed in similar to 15-20% human cancers, and K-Ras mutations account for similar to 85% of all Ras mutations. Despite the significance of Ras proteins in refractory cancers, there is no anti-Ras drug available in clinic. Since K-Ras must interact with the plasma membrane (PM) for biological activity, inhibition of the K-Ras/PM interaction is a tractable approach to block oncogenic K-Ras activity. Here, we discovered chalcones 1 and 8 exhibit anti-K-Ras activity, and show that the compounds mislocalize K-Ras from the PM and block oncogenic K-Ras signal output. Also, 1 inhibits the growth of K-Ras-driven human cancer cells. Our data suggest that 1 could be a promising starting point for developing anti-K-Ras cancer drug.