BG0402 | 130671-93-1

• 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: BG0402
• 英文别名: (2E)-3-(4-nitrophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one；(E)-1-(3,4-dimethoxyphenyl)-3-(4-nitrophenyl) prop-2-en-1-one；1-(3',4'-dimethoxyphenyl)-3-(4-nitrophenyl)propenone；3',4'-dimethoxy-4-nitro-trans-chalcone；3',4'-Dimethoxy-4-nitro-trans-chalkon；(E)-1-(3,4-dimethoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one
• CAS: 130671-93-1
• 化学式: C₁₇H₁₅NO₅
• 分子量: 313.31
• InChiKey: HASYJTSNJVEZJN-WEVVVXLNSA-N

物化性质

• 沸点：
  477.3±45.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  BG0402 在 一水合肼 、 三乙胺 、 tin(ll) chloride 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 N-(4-(1-acetyl-3-(3,4-dimethoxyphenyl)-4, 5-dihydro-1H-pyrazol-5-yl)phenyl)-3-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis, anti-inflammatory and antimicrobial evaluation of novel 1-acetyl-3,5-diaryl-4,5-dihydro (1H) pyrazole derivatives bearing urea, thiourea and sulfonamide moieties

  摘要：

  A series of novel 1-acetyl-3-(3,4-dimethoxypheny)-5-(4-(3-(arylureido/arylthioureido/arylsulfonamido) phenyl)-4,5-dihydropyrazole derivatives of biological interest have been prepared by sequential cyclization of 1-(4-nitrophenyl)-3-(3,4-dimethoxyphenyl)-pro-2-ene-1 with hydrazine hydrate, reduction followed by reaction of resulting amine with different arylisocyanates or arylisothiocyanates or arylsulfonyl chlorides. All the synthesized compounds (1- 32) have been screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Biological evaluation study showed, the compounds 4, 5, 9, 11, 14 and 16 found to have promising anti-inflammatory activity (up to 61-85% TNF-alpha and 76-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (76% TNF-alpha and 86% IL-6 inhibitory activity at 1 mu M). Compounds 24, 26, 27, 28 and 29 exhibited promising antimicrobial activity at MIC values ranging from 70 to 10 mu g/mL against all the selected pathogenic bacteria and fungi. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.118
• 作为产物：
  描述：

  对硝基苯甲醛 、 3,4-二甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以65%的产率得到BG0402
  参考文献：
  名称：

  Effect on Acetylcholinesterase and Anti-oxidant Activity of Synthetic Chalcones having a Good Predicted Pharmacokinetic Profile

  摘要：

  背景：乙酰胆碱酯酶（AChE）是开发治疗阿尔茨海默病（AD）药物的重要靶点。本研究中，我们探讨了22种合成的查尔酮对AChE活性的影响。 目标：本工作的目的是合成并评估查尔酮对AChE活性的影响，以及其抗氧化活性并预测其药代动力学特征。 方法：通过克莱森-施密特缩合合成查尔酮，并采用Elmann比色法评估其对AChE的抑制作用。为了确定抗氧化活性，选择了DPPH自由基清除法。 结果：我们发现所有查尔酮均抑制该活性，IC50值范围为0.008至4.8 µM。我们选择了活性最强的化合物19，其IC50值为0.008 µM，进行动力学研究，结果表明其呈现竞争性抑制模式。分子对接模拟显示化合物19与AChE的活性位点之间有良好的相互作用。考虑到药代动力学参数的预测是选择潜在药物候选物的有用工具，我们的研究结果表明，大多数查尔酮，包括活性最强的，具有良好的药代动力学特征和血脑屏障渗透性。反应性氧种（ROS）在AD相关事件中的参与促使我们评估这些查尔酮作为自由基清除剂的潜力。 结论：我们发现化合物19是一种有效的AChE抑制剂，基于动力学研究，它作为竞争性抑制剂发挥作用。

  DOI：

  10.2174/1573406413666170525125730

文献信息

• Parmar, Virinder S.; Jain, Subhash C.; Bisht, Kirpal S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 7, p. 628 - 643
  作者：Parmar, Virinder S.、Jain, Subhash C.、Bisht, Kirpal S.、Sharma, Nawal K.、Himanshu、Gupta, Suman、Prasad, Ashok K.、Jha, Amitabh、Poonam、Malhotra, Sanjay、Sharma, Sunil K.、Bracke, Marc E.、Errington, William、Olsen, Carl E.、Wengel, Jesper

  DOI：——

  日期：——
• NUCLEAR RECEPTOR MODULATORS AND THEIR USE FOR THE TREATMENT AND PREVENTION OF CANCER
  申请人：Neckers Jane B.

  公开号：US20140171503A1

  公开（公告）日：2014-06-19

  Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R 1 to R 5 and X 1 to X 5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.
• Synthesis, anti-inflammatory and antimicrobial evaluation of novel 1-acetyl-3,5-diaryl-4,5-dihydro (1H) pyrazole derivatives bearing urea, thiourea and sulfonamide moieties
  作者：Ashish P. Keche、Girish D. Hatnapure、Rajesh H. Tale、Atish H. Rodge、Vandana M. Kamble

  DOI：10.1016/j.bmcl.2012.08.118

  日期：2012.11

  A series of novel 1-acetyl-3-(3,4-dimethoxypheny)-5-(4-(3-(arylureido/arylthioureido/arylsulfonamido) phenyl)-4,5-dihydropyrazole derivatives of biological interest have been prepared by sequential cyclization of 1-(4-nitrophenyl)-3-(3,4-dimethoxyphenyl)-pro-2-ene-1 with hydrazine hydrate, reduction followed by reaction of resulting amine with different arylisocyanates or arylisothiocyanates or arylsulfonyl chlorides. All the synthesized compounds (1- 32) have been screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Biological evaluation study showed, the compounds 4, 5, 9, 11, 14 and 16 found to have promising anti-inflammatory activity (up to 61-85% TNF-alpha and 76-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (76% TNF-alpha and 86% IL-6 inhibitory activity at 1 mu M). Compounds 24, 26, 27, 28 and 29 exhibited promising antimicrobial activity at MIC values ranging from 70 to 10 mu g/mL against all the selected pathogenic bacteria and fungi. (C) 2012 Elsevier Ltd. All rights reserved.
• Effect on Acetylcholinesterase and Anti-oxidant Activity of Synthetic Chalcones having a Good Predicted Pharmacokinetic Profile
  作者：Renata P. Sakata、Micheli Figueiro、Daniel F. Kawano、Wanda P. Almeida

  DOI：10.2174/1573406413666170525125730

  日期：2017.10.17

  Background: Acetylcholinesterase (AChE) is an important target in the development of drug to treat Alzheimer's disease (AD). In this work, we investigated the effect of twenty-two synthesized chalcones on AChE activity. Objective: This work is aimed to synthesize and evaluate the effect of chalcones on the AChE activity, as well as anti-oxidant activity and predict their pharmacokinetic profile. Method: Chalcones were synthesized through a Claisen-Schmidt condensation and their inhibitory effect on the AChE was evaluated by the Elmann's colorimetric method. To determine the anti-oxidant activity the DPPH radical scavenging method was chosen. Results: We found that all chalcones inhibit this activity, with IC50 values ranging from 0.008 to 4.8 µM. We selected the most active compound 19 with an IC50 value of 0.008 µM for a kinetic study demonstrating a competitive inhibition mode. Molecular docking simulations showed a good interaction between 19 and the active site of AChE. Considering the prediction of pharmacokinetic parameters being a useful tool for selecting potential drug candidates, our study results suggest that the majority of chalcones, including the most active one, have a promising pharmacokinetic profile and blood-brain barrier permeability. The involvement of reactive oxygen species (ROS) in AD-related events has encouraged us to evaluate these chalcones as radical scavengers. Conclusion: We have found that compound 19 is a potent AChE inhibitor, and based on kinetic studies, it acts as a competitive inhibitor.

  背景：乙酰胆碱酯酶（AChE）是开发治疗阿尔茨海默病（AD）药物的重要靶点。本研究中，我们探讨了22种合成的查尔酮对AChE活性的影响。 目标：本工作的目的是合成并评估查尔酮对AChE活性的影响，以及其抗氧化活性并预测其药代动力学特征。 方法：通过克莱森-施密特缩合合成查尔酮，并采用Elmann比色法评估其对AChE的抑制作用。为了确定抗氧化活性，选择了DPPH自由基清除法。 结果：我们发现所有查尔酮均抑制该活性，IC50值范围为0.008至4.8 µM。我们选择了活性最强的化合物19，其IC50值为0.008 µM，进行动力学研究，结果表明其呈现竞争性抑制模式。分子对接模拟显示化合物19与AChE的活性位点之间有良好的相互作用。考虑到药代动力学参数的预测是选择潜在药物候选物的有用工具，我们的研究结果表明，大多数查尔酮，包括活性最强的，具有良好的药代动力学特征和血脑屏障渗透性。反应性氧种（ROS）在AD相关事件中的参与促使我们评估这些查尔酮作为自由基清除剂的潜力。 结论：我们发现化合物19是一种有效的AChE抑制剂，基于动力学研究，它作为竞争性抑制剂发挥作用。