(E)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(4-methylthiophenyl)prop-2-ene-1-one | 76554-27-3

• 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-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(4-methylthiophenyl)prop-2-ene-1-one
• 英文别名: (E)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(4-(methylthio)phenyl)prop-2-en-1-one；2'-hydroxy-4',6'-dimethoxy-4-(methylthio)-chalcone；2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-(methylthio)phenyl)-；(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one
• CAS: 76554-27-3
• 化学式: C₁₈H₁₈O₄S
• 分子量: 330.405
• InChiKey: UAHKGRIMCHVSAP-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 4-(甲基巯基)苯甲醛 以 乙醇 、 水 为溶剂， 以78.3%的产率得到(E)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(4-methylthiophenyl)prop-2-ene-1-one
  参考文献：
  名称：

  Flavokawain B型Chalcones的设计，合成和对接研究及其对MCF-7和MDA-MB-231细胞系的细胞毒性作用。

  摘要：

  Flavokawain B（1）是从Piper methysticum的根中提取的天然查尔酮，已被证明是潜在的细胞毒性化合物。使用黄酮类固醇B的部分结构（FKB），已经合成了约23个类似物。其中，在新的FKB衍生物中发现了化合物8、13和23。评估了所有化合物对两种乳腺癌细胞MCF-7和MDA-MB-231的细胞毒性，从而建立了结构-活性关系。FKB衍生物16（IC50 = 6.50±0.40和4.12±0.20μg/ mL），15（IC50 = 5.50±0.35和6.50±1.40μg/ mL）和13（IC50 = 7.12±0.80和4.04±0.30μg/ mL）对MCF-7和MDA-MB-231细胞系具有潜在的细胞毒性作用。但是，甲氧基在化合物2的第3位和第4位取代（IC50 = 8.90±0.60和6.80±0。35μg/ mL）和22（IC50 = 8.80±0.35和14.16±1

  DOI：

  10.3390/molecules23030616

文献信息

• Flavokawain derivative FLS induced G2/M arrest and apoptosis on breast cancer MCF-7 cell line
  作者：Yeap Swee Keong、Norlaily Mohd Ali、Nadeem M Akhtar、Huynh Ky、Kian Lam Lim、Nadiah Abu、Seema Zareen、Ho Wan Yong、Han Alan-Ong、Sheau Wei Tan、Noorjahan Banu Mohamed Alitheen、Jamil Ismail、Tunku Kamarul

  DOI：10.2147/dddt.s102164

  日期：——

  Known as naturally occurring biologically active compounds, flavokawain A and B are the leading chalcones that possess anticancer properties. Another flavokawain derivative, (E)-1-(2'-Hydroxy-4',6'-dimethoxyphenyl)-3-(4-methylthio)phenyl)prop-2-ene-1-one (FLS) was characterized with 1H-nuclear magnetic resonance, electron-impact mas spectrometry, infrared spectroscopy, and ultraviolet (H-1 NMR, EI-MS, IR, and UV) spectroscopic techniques. FLS cytotoxic efficacy against human cancer cells (MCF-7, MDA-MB-231, and MCF-10A) resulted in the reduction of IC50 values in a time-and dose-dependent mode with high specificity on MCF-7 ( IC50 of 36 mu M at 48 hours) against normal breast cell MCF-10A (no IC50 detected up to 180 mu M at 72 hours). Light, scanning electron, and fluorescent microscopic analysis of MCF-7 cells treated with 36 mu M of FLS displayed cell shrinkage, apoptotic body, and DNA fragmentation. Additionally, induction of G2/M cell arrest within 24 hours and apoptosis at subsequent time points was discovered via flow cytometry analysis. The roles of PLK-1, Wee-1, and phosphorylation of CDC-2 in G2/M arrest and proapoptotic factors (Bax, caspase 9, and p53) in promotion of apoptosis of FLS against MCF-7 cells were discovered using fluorometric, quantitative real-time polymerase chain reaction, and Western blot analysis. Interestingly, the presence of SCH3 (thiomethyl group) on ring B structure contributed to the selective cytotoxicity against MCF-7 cells compared to other chalcones, flavokawain A and B. Overall, our data suggest potential therapeutic value for flavokawain derivative FLS to be further developed as a new anticancer drug.
• US4327088A
  申请人：——

  公开号：US4327088A

  公开（公告）日：1982-04-27
• US4605674A
  申请人：——

  公开号：US4605674A

  公开（公告）日：1986-08-12