(E)-3-(4-hydroxyphenyl)-1-(pyridin-3-yl)prop-2-en-1-one | 16764-47-9

• 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: (E)-3-(4-hydroxyphenyl)-1-(pyridin-3-yl)prop-2-en-1-one
• 英文别名: (E)-3-(4-hydroxy-phenyl)-1-pyridin-3-yl-propenone；(E)-3-(4-hydroxyphenyl)-1-pyridin-3-ylprop-2-en-1-one
• CAS: 16764-47-9；16212-38-7
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: IYPHTBFFSWNNED-VMPITWQZSA-N

物化性质

• 沸点：
  420.066±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.241±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-hydroxyphenyl)-1-(pyridin-3-yl)prop-2-en-1-one 、 2-氯-N,N-二甲基乙胺 以17%的产率得到
  参考文献：
  名称：

  BRADLEROVA, A.;DURINDA, J.;MISIKOVA, E., CHEM. ZVESTI, 1983, 37, N 2, 251-252

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-(pyridin-3-yl)-3-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以72%的产率得到(E)-3-(4-hydroxyphenyl)-1-(pyridin-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  Hydroxy-substituted trans -cinnamoyl derivatives as multifunctional tools in the context of Alzheimer's disease

  摘要：

  Alzheimer's disease (AD) is a multifactorial pathology that requires multifaceted agents able to address its peculiar nature. In recent years, a plethora of proteins and biochemical pathways has been proposed as possible targets to counteract neurotoxicity. Although the complex scenario is not completely elucidated, close relationships are emerging among some of these actors. In particular, increasing evidence has shown that aggregation of amyloid beta (A beta), glycogen synthase kinase 3 beta (GSK-3 beta) and oxidative stress are strictly interconnected and their concomitant modulation may have a positive and synergic effect in contrasting AD-related impairments. We designed compound 3 which demonstrated the ability to inhibit both GSK-3 beta (IC50 = 24.36 +/- 0.01 mu M) and A beta(42) self-aggregation (IC50 = 9.0 +/- 1.4 mu M), to chelate copper (II) and to act as exceptionally strong radical scavenger (k(inh) = 6.8 +/- 0.5 . 10(5) M(-1)s(-1)) even in phosphate buffer at pH 7.4 (k(inh) = 3.2 +/- 0.5 . 10(5) M(-1)s(-1)). Importantly, compound 3 showed high predicted blood-brain barrier permeability, did not exert any significant cytotoxic effects in immature cortical neurons up to 50 mu M and showed neuroprotective properties at micromolar concentration against toxic insult induced by glutamate. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.07.058

文献信息

• Anti-Tumor Activity of New Artemisinin-Chalcone Hybrids
  作者：Lijun Xie、Xin Zhai、Chun Liu、Peng Li、Yangxiong Li、Guoxian Guo、Ping Gong

  DOI：10.1002/ardp.201000391

  日期：2011.10

  develop potent and selective anti‐tumor agents, three new series of artemisinin–chalcone hybrids 10a–10g, 11a–11g and 12a–12h were designed, synthesized and screened for their anti‐tumor activity against five cell lines (HT‐29, A549, MDA‐MB‐231, HeLa and H460) in vitro. Among compounds 10a–g and 11a–11g, most of them displayed enhanced activity and good selectivity toward HT‐29 and HeLa cell lines

  为了开发有效和选择性的抗肿瘤药物，设计、合成了三个新系列的青蒿素-查尔酮杂交体 10a-10g、11a-11g 和 12a-12h，并筛选了它们对五种细胞系（HT ‐29、A549、MDA-MB-231、HeLa 和 H460) 体外。在化合物 10a-g 和 11a-11g 中，与 DHA（双氢青蒿素）相比，大多数化合物对 HT-29 和 HeLa 细胞系表现出增强的活性和良好的选择性，IC50 值范围为 0.12 至 0.85 µM。化合物 10a 和 11a 对 HeLa 细胞最有活性，IC50 值为 0.12 和 0.19 µM。结果表明查耳酮部分的存在有利于它们的活性和选择性。此外，含有“反向查耳酮”部分的化合物 12a-12h 的活性仅比 DHA 略有提高。
• [EN] ESTROGENIC COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS ŒSTROGÉNIQUES ET MÉTHODES D'UTILISATION
  申请人：[en]IATERION, INC.

  公开号：WO2024026034A1

  公开（公告）日：2024-02-01

  Estrogenic compounds, compositions and method are presented. The novel estrogenic compounds comprise novel chalcone derivatives and analogs that have little or no measurable estrogen (estradiol, E2) activity but potentiate E2 activity without binding an estrogen receptor (ER). The novel compositions comprise one or more of the novel estrogenic compounds, and may optionally comprise one or more excipients. The one or more excipients may be pharmaceutically acceptable. The one or more excipients may comprise at least one compound that does not occur in nature with estrogenic compounds. The method comprises administering a pharmaceutical composition comprising an estrogenic compound described herein to a patient in need of treatment with an estrogenic compound or pharmaceutical composition.
• Hydroxy-substituted trans -cinnamoyl derivatives as multifunctional tools in the context of Alzheimer's disease
  作者：Angela De Simone、Manuela Bartolini、Andrea Baschieri、Kim Y.P. Apperley、Huan Huan Chen、Melissa Guardigni、Serena Montanari、Tereza Kobrlova、Ondrej Soukup、Luca Valgimigli、Vincenza Andrisano、Jeffrey W. Keillor、Manuela Basso、Andrea Milelli

  DOI：10.1016/j.ejmech.2017.07.058

  日期：2017.10

  Alzheimer's disease (AD) is a multifactorial pathology that requires multifaceted agents able to address its peculiar nature. In recent years, a plethora of proteins and biochemical pathways has been proposed as possible targets to counteract neurotoxicity. Although the complex scenario is not completely elucidated, close relationships are emerging among some of these actors. In particular, increasing evidence has shown that aggregation of amyloid beta (A beta), glycogen synthase kinase 3 beta (GSK-3 beta) and oxidative stress are strictly interconnected and their concomitant modulation may have a positive and synergic effect in contrasting AD-related impairments. We designed compound 3 which demonstrated the ability to inhibit both GSK-3 beta (IC50 = 24.36 +/- 0.01 mu M) and A beta(42) self-aggregation (IC50 = 9.0 +/- 1.4 mu M), to chelate copper (II) and to act as exceptionally strong radical scavenger (k(inh) = 6.8 +/- 0.5 . 10(5) M(-1)s(-1)) even in phosphate buffer at pH 7.4 (k(inh) = 3.2 +/- 0.5 . 10(5) M(-1)s(-1)). Importantly, compound 3 showed high predicted blood-brain barrier permeability, did not exert any significant cytotoxic effects in immature cortical neurons up to 50 mu M and showed neuroprotective properties at micromolar concentration against toxic insult induced by glutamate. (C) 2017 Elsevier Masson SAS. All rights reserved.
• BRADLEROVA, A.;DURINDA, J.;MISIKOVA, E., CHEM. ZVESTI, 1983, 37, N 2, 251-252
  作者：BRADLEROVA, A.、DURINDA, J.、MISIKOVA, E.

  DOI：——

  日期：——