(E)-3-(3-hydroxyphenyl)-1-(3-pyridyl)prop-2-en-1-one | 16212-35-4

• 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-(3-hydroxyphenyl)-1-(3-pyridyl)prop-2-en-1-one
• 英文别名: (E)-3-(3-hydroxyphenyl)-1-(pyridin-3-yl)prop-2-en-1-one；DMU767；(2E)-3-(3-hydroxyphenyl)-1-pyridin-3-ylprop-2-en-1-one；(E)-3-(3-hydroxyphenyl)-1-pyridin-3-ylprop-2-en-1-one
• CAS: 16212-35-4
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: YWQFCRRNTSUDQK-VOTSOKGWSA-N

物化性质

• 熔点：
  192-193 °C
• 沸点：
  441.142±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

• 作为产物：
  描述：

  3-(tetrahydro-2H-2-pyranyloxy)benzaldehyde 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 (E)-3-(3-hydroxyphenyl)-1-(3-pyridyl)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

• Certain pyrazoline derivatives with kinase inhibitory activity
  申请人：Adams Ruth S.

  公开号：US20080171754A1

  公开（公告）日：2008-07-17

  The present invention provides certain pyrazoline compounds useful as inhibitors of protein kinases. The invention also provides pharmaceutical compositions and methods of using the compositions in the treatment of various diseases.

  本发明提供了某些吡唑啉化合物，可用作蛋白激酶的抑制剂。该发明还提供了药物组合物和使用这些组合物治疗各种疾病的方法。
• Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines
  作者：Neill J. Horley、Kenneth J.M. Beresford、Tarun Chawla、Glen J.P. McCann、Ketan C. Ruparelia、Linda Gatchie、Vinay R. Sonawane、Ibidapo S. Williams、Hoon L. Tan、Prashant Joshi、Sonali S. Bharate、Vikas Kumar、Sandip B. Bharate、Bhabatosh Chaudhuri

  DOI：10.1016/j.ejmech.2017.02.016

  日期：2017.3

  The structure of alpha-napthoflavone (ANF), a potent inhibitor of CYP1A1 and CYP1B1, mimics the structure of chalcones. Two potent CYP1B1 inhibitors 7k (DMU2105) and 6j (DMU2139) have been identified from two series of synthetic pyridylchalcones. They inhibit human CYP1B1 enzyme bound to yeast-derived microsomes (Sacchrosomes((TM))) with IC50 values of 10 and 9 nM, respectively, and show a very high level of selectivity towards CYP1B1 with respect to the IC50 values obtained with CYP1A1, CYP1A2, CYP3A4, CYP2D6, CYP2C9 and CYP2C19 Sacchrosomes((TM)). Both compounds also potently inhibit CYP1B1 expressed within 'live' recombinant yeast and human HEK293 kidney cells with IC50 values of 63, 65, and 4, 4 nM, respectively. Furthermore, the synthesized pyridylchalcones possess better solubility and lipophilicity values than ANF. Both compounds overcome cisplatine-resistance in HEK293 and A2780 cells which results from CYP1B1 overexpression. These potent cell-permeable and water-soluble CYP1B1 inhibitors are likely to have useful roles in the treatment of cancer, glaucoma, ischemia and obesity. (C) 2017 Elsevier Masson SAS. All rights reserved.
• US7795249B2
  申请人：——

  公开号：US7795249B2

  公开（公告）日：2010-09-14
• [EN] CERTAIN PYRAZOLINE DERIVATIVES WITH KINASE INHIBITORY ACTIVITY<br/>[FR] CERTAINS DÉRIVÉS DE PYRAZOLINE AVEC UNE ACTIVITÉ INHIBITRICE DE KINASE
  申请人：MILLENNIUM PHARM INC

  公开号：WO2008079277A1

  公开（公告）日：2008-07-03

  [EN] The present invention provides certain pyrazoline compounds useful as inhibitors of protein kinases. The invention also provides pharmaceutical compositions and methods of using the compositions in the treatment of various diseases.
  [FR] La présente invention propose certains composés de pyrazoline qui s'utilisent en tant qu'inhibiteur des protéines kinases. L'invention concerne également des compositions pharmaceutiques et des procédés d'utilisation des compositions dans le traitement de diverses maladies.
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：UNIV MONTFORT

  公开号：WO2015166043A1

  公开（公告）日：2015-11-05

  The invention relates to a compound of formula (I) for use in the prevention and/or treatment of cancer, wherein rings A and B are independently an optionally substituted aryl or an optionally substituted heteroaryl. The compounds are particularly provided for the prevention and/or treatment of hormone- induced cancers, such as breast, ovarian, uterine, endometrial and prostate cancer.