(E)-1-(3-pyridyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-lone

• 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)-1-(3-pyridyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-lone
• 英文别名: (E)-1-(pyridin-3-yl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one；DMU2117；(E)-1-pyridin-3-yl-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: BJLXVSGXKPEVHK-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-乙酰基吡啶 、 2,3,4-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以70%的产率得到(E)-1-(3-pyridyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-lone
  参考文献：
  名称：

  氮杂查耳酮的合成、α-淀粉酶、α-葡萄糖苷酶抑制活性、动力学和分子对接研究

  摘要：

  糖尿病作为一种慢性代谢紊乱引起了药物化学家和生物学家的关注。由于糖尿病在世界范围内的流行程度不断提高，因此引入用于治愈和治疗糖尿病的新的和潜在的候选药物已成为一个主要问题。在当前的研究中，合成了27 种氮杂查尔酮衍生物3-29，并通过抑制α-淀粉酶和α-葡萄糖苷酶来评估它们的抗高血糖活性。五种化合物3 (IC 50 = 23.08 ± 0.03 µ M)、(IC 50 = 26.08 ± 0.43 µ M)、5 (IC 50 = 24.57 ± 0.07 µ M)、(IC50 = 27.57 ± 0.07 µ M)、6 (IC 50 = 24.94 ± 0.12 µ M)、(IC 50 = 27.13 ± 0.08 µ M)、16 (IC 50 = 27.57 ± 0.07 µ M)、(IC 50 = 29.13 = 0.18 µ M) 和28 (IC 50 = 26.94 ± 0.12 µ

  DOI：

  10.1016/j.bioorg.2020.104489

文献信息

• 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.
• [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.
• Synthesis of azachalcones, their α-amylase, α-glucosidase inhibitory activities, kinetics, and molecular docking studies
  作者：Faiza Saleem、Kanwal、Khalid Mohammed Khan、Sridevi Chigurupati、Mehwish Solangi、Appala Raju Nemala、Maria Mushtaq、Zaheer Ul-Haq、Muhammad Taha、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2020.104489

  日期：2021.1

  12 µM), (IC50 = 27.13 ± 0.08 µM), 16 (IC50 = 27.57 ± 0.07 µM), (IC50 = 29.13 ± 0.18 µM), and 28 (IC50 = 26.94 ± 0.12 µM) (IC50 = 27.99 ± 0.09 µM) demonstrated good inhibitory activities against α-amylase and α-glucosidase enzymes, respectively. Acarbose was used as the standard in this study. Structure-activity relationship was established by considering the parent skeleton and different substitutions

  糖尿病作为一种慢性代谢紊乱引起了药物化学家和生物学家的关注。由于糖尿病在世界范围内的流行程度不断提高，因此引入用于治愈和治疗糖尿病的新的和潜在的候选药物已成为一个主要问题。在当前的研究中，合成了27 种氮杂查尔酮衍生物3-29，并通过抑制α-淀粉酶和α-葡萄糖苷酶来评估它们的抗高血糖活性。五种化合物3 (IC 50 = 23.08 ± 0.03 µ M)、(IC 50 = 26.08 ± 0.43 µ M)、5 (IC 50 = 24.57 ± 0.07 µ M)、(IC50 = 27.57 ± 0.07 µ M)、6 (IC 50 = 24.94 ± 0.12 µ M)、(IC 50 = 27.13 ± 0.08 µ M)、16 (IC 50 = 27.57 ± 0.07 µ M)、(IC 50 = 29.13 = 0.18 µ M) 和28 (IC 50 = 26.94 ± 0.12 µ