4'-hydroxy-4-methoxychalcone | 6338-81-4

• 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: 4'-hydroxy-4-methoxychalcone
• 英文别名: 1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one；4-Methoxy-4'-hydroxychalcone；1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 6338-81-4
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: RTCVAWRRHHSOCC-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C(Solv: ethanol (64-17-5))
• 沸点：
  467.0±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  4'-hydroxy-4-methoxychalcone 在 potassium carbonate 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 1-(5-(4-methoxyphenyl)-3-(4-(prop-2-yn-1-yloxy)phenyl)-4,5- dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline—isatin hybrids

  摘要：

  Numerous reports highlighting the cytotoxic effects of 3,5-diaryl N-acetyl-pyrazolines and isatin tempted us to synthesise conjugates of the functionalities via alkyl armed triazole tetheration. The hybrids were synthesized by click chemistry approach and were evaluated against a panel of cell lines i.e. viz HeLa (cervix cancer), CAKI-I (Renal cancer), PC-3 (Prostate cancer) and Miapaca-2 (pancreatic cancer). The hybrids were classified into right-handed and left-handed conjugates on the basis of the placement of the isatin ring. The length of the alkyl armed triazole linker was varied from 2 to 6. Structure activity relationship has also been presented. A preliminary cytotoxic assay was performed on the series of 3,5-diaryl N-acetyl-pyrazolines and only the potent 3,5-diaryl N-acetyl-pyrazolines were selected for their inclusion in the hybrid scaffold. Among the cell lines employed, HeLa cell line was the most sensitive towards the exposure of test compounds. Out of all the compounds evaluated, two right-handed conjugates MI-7b and MI-8b and two left-handed conjugates MI-4b, MI-6b displayed significant cytotoxic potential and exhibited an IC50 range from 1.3 to 3.5 mu M against HeLa Cell line..

  DOI：

  10.1007/s00044-014-1001-5
• 作为产物：
  描述：

  4-甲氧基肉桂酸 在 正丁基锂 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 4'-hydroxy-4-methoxychalcone
  参考文献：
  名称：

  在肝细胞癌小鼠模型中发现 CAPE 衍生物作为具有抗癌活性的双重 EGFR 和 CSK 抑制剂

  摘要：

  咖啡酸苯乙酯（CAPE）是一种从蜂巢蜂胶中提取的生物活性成分，可以抑制肝细胞癌（HCC）。为了探索更稳定的 CAPE 衍生物，设计、合成了 25 种化合物，并进行了体外和体内药理学评估，作为 HCC 的抗肿瘤剂。化合物8d、8f、8l、8j和8k在HCC细胞系中显示出比包括CAPE在内的其他化合物有利的抗增殖活性。根据QTRP（Quantitative Thiol Reactivity Profiling）的结果，表皮生长因子受体（EGFR）和C端Src激酶（CSK）被认为是8f的靶标，这通过结合模式分析得到证实。此外，在 ADP-Glo​​™ 激酶测定中，化合物8f、8l、8j、8k、8g和8h对 CSK 和 EGFR 均显示出强于其他衍生物的抑制作用。代表性化合物8f有效抑制小鼠模型中的各种肿瘤生长，包括小鼠肝细胞癌 H22，同时下调 EGFR/AKT 通路并通过抑制 CSK 增强 T

  DOI：

  10.1016/j.bioorg.2020.104536

文献信息

• Bis(4,5-dihydropyrazole) Derivatives: Synthesis, Characterization and Antimicrobial-Antioxidant Evaluations
  作者：Mohamad Yusuf、Saloni Thakur

  DOI：10.14233/ajchem.2018.21451

  日期：——

  In the present work, five new bispyrazolines 3(a-e) have been prepared from the cyclization reaction of bischalcones 2(a-e) with phenyl hydrazine under alcoholic medium. The bischalcones 2(a-e) were synthesized by using the alkylation of chalcone 1 with appropriate alkylating agents. The structures of the newly prepared products were confirmed by IR, 1H and 13C NMR and ESI-MS. The final products were screened for their antimicrobial and antioxidant properties. The ortho-xylene linked bispyrazoline showed significant antimicrobial action while the bischalcones proved themselves significant antioxidant.

  本研究中，从双查尔酮2(a-e)与苯肼在醇介质中的环化反应中制备了五种新的双吡唑啉3(a-e)。通过用适当的烷基化剂对查尔酮1进行烷基化反应合成了双查尔酮2(a-e)。通过IR、1H和13C NMR以及ESI-MS确认了新制备产品的结构。最终产品经过抗菌和抗氧化性质的筛选。邻二甲苯连接的双吡唑啉显示出显著的抗菌作用，而双查尔酮则表现出显著的抗氧化性。
• One-Pot Three-Component Synthesis of 2-Amino Pyrimidines in Aqueous PEG-400 at Ambient Temperature
  作者：Dhanaji V. Jawale、Umesh R. Pratap、Manisha R. Bhosale、Ramrao A. Mane

  DOI：10.1002/jhet.673

  日期：2016.9

  Amino pyrimidines have been synthesized by a one‐pot procedure under environmentally friendly reaction conditions at room temperature. The use of aqueous PEG‐400 circumvents the problems associated with the toxic, hazardous organic solvents and oxidizing agents.

  氨基嘧啶是在室温下在环境友好的反应条件下通过一锅法合成的。使用水性PEG-400可以避免与有毒，有害的有机溶剂和氧化剂有关的问题。
• Structure-activity relationship with pyrazoline-based aromatic sulfamates as carbonic anhydrase isoforms I, II, IX and XII inhibitors: Synthesis and biological evaluation
  作者：Davide Moi、Alessio Nocentini、Alessandro Deplano、Gianfranco Balboni、Claudiu T. Supuran、Valentina Onnis

  DOI：10.1016/j.ejmech.2019.111638

  日期：2019.11

  Four new series of aromatic sulfamates were synthesized and investigated for the inhibition of four human (h) isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), hCA I, II, IX, and XII. The reported derivatives, obtained by a sulfamoylation reaction of the corresponding phenolic precursors, bear 3,5-diarylpyrazoline moieties as spacers between the benzenesulfamate fragment which binds the

  合成了四个新系列的芳族氨基磺酸盐，并研究了它们对锌酶碳酸酐酶（CA，EC 4.2.1.1），hCA I，II，IX和XII的四种人（h）同工型的抑制作用。通过相应的酚类前体的氨磺酰化反应获得的已报道的衍生物带有3,5-二芳基吡唑啉部分，作为结合来自活性位点的锌离子的苯氨基磺酸盐片段和抑制剂尾巴之间的间隔基。吡唑啉是具有生物学优势的支架，具有多种生物活性，例如抗增殖作用。测试了这些衍生物对胞质，hCA I和II（脱靶同种型）和跨膜，与肿瘤相关的hCA IX和XII酶（抗癌靶标）的抑制作用。通常，hCA I不能被有效抑制，而许多低纳摩尔抑制剂被证明可抵抗hCA II（KIs在0.42-90.1 nM范围内），IX（KIs在0.72-63.6 nM范围内）和XII（KIs在0.88-85.2 nM范围内）。对于CA II，吡唑啉环上的最佳取代片段包括3-芳基上的4-氨基磺酸基和5-芳基上的卤素或
• Synthesis of Chalcones with Anticancer Activities
  作者：Suvitha Syam、Siddig Ibrahim Abdelwahab、Mohammed Ali Al-Mamary、Syam Mohan

  DOI：10.3390/molecules17066179

  日期：——

  Several chalcones were synthesized and their in vitro cytotoxicity against various human cell lines, including human breast adenocarcinoma cell line MCF-7, human lung adenocarcinoma cell line A549, human prostate cancer cell line PC3, human adenocarcinoma cell line HT-29 (colorectal cancer) and human normal liver cell line WRL-68 was evaluated. Most of the compounds being active cytotoxic agents, four of them with minimal IC50 values were chosen and studied in detail with MCF-7 cells. The compounds 1, 5, 23, and 25 were capable in eliciting apoptosis in MCF-7 cells as shown by multiparameter cytotoxicity assay and caspase-3/7, -8, and -9 activities (p < 0.05). The ROS level showed 1.3-fold increase (p < 0.05) at the low concentrations used and thus it was concluded that the compounds increased the ROS level eventually leading to apoptosis in MCF-7 cells through intrinsic as well as extrinsic pathways.

  合成了几种查尔酮，并评价了它们对多种人类细胞系的体外细胞毒性，包括人乳腺腺癌细胞系MCF-7、人肺腺癌细胞系A549、人前列腺癌细胞系PC3、人腺癌细胞系HT-29（结直肠癌）以及人正常肝细胞系WRL-68。大多数化合物作为有效的细胞毒剂，其中四种具有最小IC50值的化合物被选中并详细研究了对MCF-7细胞的影响。化合物1、5、23和25能够引发MCF-7细胞的凋亡， multiparameter细胞毒性测定和caspase-3/7、-8、-9活性表明了这一点（p < 0.05）。在使用的低浓度下，活性氧（ROS）水平显示出1.3倍的增加（p < 0.05），因此得出结论，这些化合物提高了ROS水平，最终通过内源性和外源性途径导致MCF-7细胞凋亡。
• Aldoxime- and hydroxy-functionalized chalcones as highly potent and selective monoamine oxidase-B inhibitors
  作者：Jong Min Oh、T.M. Rangarajan、Reeta Chaudhary、Nicola Gambacorta、Orazio Nicolotti、Sunil Kumar、Bijo Mathew、Hoon Kim

  DOI：10.1016/j.molstruc.2021.131817

  日期：2022.2

  index (SI) of 1,113. HC3 also potently inhibited MAO-B (IC50 = 0.0067 µM) and had the highest SI (1,455). ACE7 and ACE15 were also potent MAO-B inhibitors (IC50 = 0.012 and 0.018 µM, respectively), with SIs of 260 and 1,161, respectively. HC3 and HC6 were reversible competitive inhibitors of MAO-B, with Ki values of 0.0036 and 0.0013 μM, respectively. A structure–activity relationship revealed that methyl

  评估了一组 30 种查尔酮衍生物，包括 19 种醛肟-查尔酮醚 (ACE) 和 11 种羟基-查尔酮 (HC)，这些衍生物之前使用 Pd 催化的 C-O 交叉偶联方法合成，用于评估它们对单胺氧化酶的抑制活性。 MAO)、胆碱酯酶 (ChE) 和 β-分泌酶 (BACE-1)。HC6 是最有效的 MAO-B 抑制剂，IC 50值为 0.0046 µM，选择性指数 (SI) 为 1,113。HC3 还有效抑制 MAO-B (IC 50  = 0.0067 µM) 并具有最高的 SI (1,455)。ACE7 和 ACE15 也是有效的 MAO-B 抑制剂（IC 50 分别 为 0.012 和 0.018 µM），SI 分别为 260 和 1,161。HC3 和 HC6 是 MAO-B 的可逆竞争性抑制剂，K i值分别为 0.0036 和 0.0013 μM。构效关系表明甲基和氟取代基有助于增加抑制和选择性。ACE7