(E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one | 937820-86-5

• 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-(benzo[d][1,3]dioxol-5-yl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one
• 英文别名: (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one；(2E)-1-(1,3-benzodioxol-5-yl)-3-(3-methoxy-4-hydroxyphenyl)-2-propen-1-one；1-(benzo[d][1,3]dioxol-6-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one；(E)-1-(1,3-benzodioxol-5-yl)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-en-1-one；(E)-1-(1,3-benzodioxol-5-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
• CAS: 937820-86-5
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: HZBLJZNQIGZHMZ-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one 在 盐酸 、 sodium tetrahydroborate 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 4-(3-(benzo[d][1,3]dioxol-6-yl)allyl)-2-methoxyphenol
  参考文献：
  名称：

  Syntheses of 2-methoxyestradiol and eugenol template based diarylpropenes as non-steroidal anticancer agents

  摘要：

  基于2-甲氧基雌二醇（1）和丁子香酚（6）模板，合成了构象灵活和刚性的二芳基丙烯类化合物14(a–l)与20(a–e)，作为非甾体抗肿瘤药物。采用SRB法评估了这些合成化合物在体外对人癌细胞系MCF-7、A549、DU 145、KB和MDA-MB-231的抗肿瘤活性。化合物14i、14k和15a在不同癌细胞系中显示显著的抗肿瘤活性，IC50值介于10.27 μM至27.91 μM之间。活性最高的分子14k通过诱导凋亡和阻滞细胞周期于G2/M期来抑制细胞增殖。在正常肝单核细胞（THP-1）中进行的体外毒性测试显示，这些化合物（14i、14k和15a）对癌细胞与健康细胞具有高度的选择性。

  DOI：

  10.1039/c4ra03823a
• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 、 香草醛 在 lithium hydroxide monohydrate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以37.4%的产率得到(E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  基于龙血中支架的成人海马神经发生有效刺激物的发现

  摘要：

  由衰老和神经系统疾病引起的海马神经发生减少会损害神经回路并导致记忆丧失。一种新的铅化合物（ñ -反式-3'，4'- methylenedioxystilben -4-基乙酰胺27）已发现有效地刺激成年大鼠的神经发生。深入的结构-活性关系研究证明，在高度细胞毒性类似物（如查耳酮和杂芳基环）和无活性类似物（如二苯乙炔和二苯乙烷）中不存在二苯乙烯骨架的必要性，并验证了氨甲酰胺和苯环上的亚甲二氧基取代基。免疫组织化学染色和生化分析表明，与先前报道的神经保护化学物质相比，N-二苯乙烯基羧酰胺具有神经增殖型神经发生的额外能力，从而为提高成年哺乳动物脑的可塑性提供了基础。

  DOI：

  10.1016/j.ejmech.2017.05.025

文献信息

• Synthesis, Biological Evaluation, And Molecular Modeling of Chalcone Derivatives As Potent Inhibitors of Mycobacterium tuberculosis Protein Tyrosine Phosphatases (PtpA and PtpB)
  作者：Louise Domeneghini Chiaradia、Priscila Graziela Alves Martins、Marlon Norberto Sechini Cordeiro、Rafael Victorio Carvalho Guido、Gabriela Ecco、Adriano Defini Andricopulo、Rosendo Augusto Yunes、Javier Vernal、Ricardo José Nunes、Hernán Terenzi

  DOI：10.1021/jm2012062

  日期：2012.1.12

  Tuberculosis (TB) is a major infectious disease caused by Mycobacterium tuberculosis (Mtb). According to the World Health Organization (WHO), about 1.8 million people die from TB and 10 million new cases are recorded each year. Recently, a new series of naphthylchalcones has been identified as inhibitors of Mtb protein tyrosine phosphatases (PTPs). In this work, 100 chalcones were designed, synthesized, and investigated for their inhibitory properties against MtbPtps. Structure-activity relationships (SAR) were developed, leading to the discovery of new potent inhibitors with IC50 values in the low-micromolar range. Kinetic studies revealed competitive inhibition and high selectivity toward the Mtb enzymes. Molecular modeling investigations were carried out with the aim of revealing the most relevant structural requirements underlying the binding affinity and selectivity of this series of inhibitors as potential anti-TB drugs.
• Efficient Synthesis and Neuroprotective Effect of Substituted 1,3-Diphenyl-2-propen-1-ones
  作者：Jae-Chul Jung、Soyong Jang、Yongnam Lee、Dongguk Min、Eunyoung Lim、Heyin Jung、Miyeon Oh、Seikwan Oh、Mankil Jung

  DOI：10.1021/jm800221g

  日期：2008.7

  An efficient synthesis involving a key aldol reaction and biological properties of 1,3-diphenyl-2-propen-1-ones 8-20 is described. The in vitro activity for 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging of 10 and 11 was 2 times higher than that for resveratrol. Compounds 9 and 11 were the strongest in suppression of in vitro nitric oxide (NO) generation and antiexcitotoxicity. Molecular modeling proposes an electron-donating group at the para position of acetophenones that leads to a dramatic increase in the suppression of NO production.
• Discovery of efficient stimulators for adult hippocampal neurogenesis based on scaffolds in dragon's blood
  作者：Jian-Hua Liang、Liang Yang、Si Wu、Si-Si Liu、Mark Cushman、Jing Tian、Nuo-Min Li、Qing-Hu Yang、He-Ao Zhang、Yun-Jie Qiu、Lin Xiang、Cong-Xuan Ma、Xue-Meng Li、Hong Qing

  DOI：10.1016/j.ejmech.2017.05.025

  日期：2017.8

  discovered to efficiently stimulate adult rats' neurogenesis. In-depth structure-activity relationship studies proved the necessity of a stilbene scaffold that is absent in highly cytotoxic analogs such as chalcones and heteroaryl rings and inactive analogs such as diphenyl acetylene and diphenyl ethane, and validated the importance of an NH in the carboxamide and a methylenedioxy substituent on the

  由衰老和神经系统疾病引起的海马神经发生减少会损害神经回路并导致记忆丧失。一种新的铅化合物（ñ -反式-3'，4'- methylenedioxystilben -4-基乙酰胺27）已发现有效地刺激成年大鼠的神经发生。深入的结构-活性关系研究证明，在高度细胞毒性类似物（如查耳酮和杂芳基环）和无活性类似物（如二苯乙炔和二苯乙烷）中不存在二苯乙烯骨架的必要性，并验证了氨甲酰胺和苯环上的亚甲二氧基取代基。免疫组织化学染色和生化分析表明，与先前报道的神经保护化学物质相比，N-二苯乙烯基羧酰胺具有神经增殖型神经发生的额外能力，从而为提高成年哺乳动物脑的可塑性提供了基础。
• Syntheses of 2-methoxyestradiol and eugenol template based diarylpropenes as non-steroidal anticancer agents
  作者：Vinay Pathak、Imran Ahmad、Amandeep Kaur Kahlon、Mohammad Hasanain、Sandeep Sharma、Kishore K. Srivastava、Jayanta Sarkar、Karuna Shankar、Ashok Sharma、Atul Gupta

  DOI：10.1039/c4ra03823a

  日期：——

  Syntheses of 2-methoxyestradiol (1) and eugenol (6) template based conformationally flexible and rigid diarylpropenes, 14(a–l) and 20(a–e), as nonsteroidal anticancer agents have been performed. The synthesized compounds were evaluated for their anticancer activity in in vitro using a panel of human cancer cell lines viz. MCF-7, A549, DU 145, KB and MDA-MB-231by SRB assay. Compounds 14i, 14k and 15a showed significant anticancer activity at IC50 between 10.27 μM to 27.91 μM in different cancer cell lines. The most active molecule, 14k, inhibited proliferation of cells by inducing apoptosis and arresting the cell cycle at the G2/M phase. In vitro toxicity of these compounds (14i, 14k and 15a) in healthy hepatic monocyte (THP-1) cells showed high selectivity of compounds towards cancerous vs. healthy cells.

  基于2-甲氧基雌二醇（1）和丁子香酚（6）模板，合成了构象灵活和刚性的二芳基丙烯类化合物14(a–l)与20(a–e)，作为非甾体抗肿瘤药物。采用SRB法评估了这些合成化合物在体外对人癌细胞系MCF-7、A549、DU 145、KB和MDA-MB-231的抗肿瘤活性。化合物14i、14k和15a在不同癌细胞系中显示显著的抗肿瘤活性，IC50值介于10.27 μM至27.91 μM之间。活性最高的分子14k通过诱导凋亡和阻滞细胞周期于G2/M期来抑制细胞增殖。在正常肝单核细胞（THP-1）中进行的体外毒性测试显示，这些化合物（14i、14k和15a）对癌细胞与健康细胞具有高度的选择性。