(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
• Design, Synthesis and Docking Studies of Flavokawain B Type Chalcones and Their Cytotoxic Effects on MCF-7 and MDA-MB-231 Cell Lines
  作者：Addila Abu Bakar、Muhammad Akhtar、Norlaily Mohd Ali、Swee Yeap、Ching Quah、Wan-Sin Loh、Noorjahan Alitheen、Seema Zareen、Zaheer Ul-Haq、Syed Shah

  DOI：10.3390/molecules23030616

  日期：——

  Flavokawain B (1) is a natural chalcone extracted from the roots of Piper methysticum, and has been proven to be a potential cytotoxic compound. Using the partial structure of flavokawain B (FKB), about 23 analogs have been synthesized. Among them, compounds 8, 13 and 23 were found in new FKB derivatives. All compounds were evaluated for their cytotoxic properties against two breast cancer cell lines

  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