2-mercapto-6-(naphthalen-2-yl)pyrimidin-4(3H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-mercapto-6-(naphthalen-2-yl)pyrimidin-4(3H)-one
• 英文别名: 6-naphthalen-2-yl-2-sulfanylidene-1H-pyrimidin-4-one
• 化学式: C₁₄H₁₀N₂OS
• mdl: MFCD21051117
• 分子量: 254.312
• InChiKey: JVFBDPVMTYLARU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-mercapto-6-(naphthalen-2-yl)pyrimidin-4(3H)-one 在 potassium carbonate 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  Identification of novel quinazoline derivatives as potent antiplasmodial agents

  摘要：

  Despite the recent reductions in the global burden of malaria, this disease remains a devastating cause of death in tropical and subtropical regions. As there is no broadly effective vaccine for malaria, prevention and treatment still rely on chemotherapy. Unfortunately, emerging resistance to the gold standard artemisinin combination therapies means that new drugs with novel modes of action are urgently needed. In this context, Plasmodium histone modifying enzymes have emerged as potential drug targets, prompting us to develop and optimize compounds directed against such epigenetic targets. A panel of 51 compounds designed to target different epigenetic enzymes were screened for activity against Plasmodium falciparum parasites. Based on in vitro activity against drug susceptible and drug-resistant P. falciparum lines, selectivity index criterion and favorable pharmacokinetic properties, four compounds, one HDAC inhibitor (1) and three DNMT inhibitors (37,43 and 45), were selected for preclinical studies in a mouse model of malaria. In vivo data showed that 37, 43 and 45 exhibited oral efficacy in the mouse model of Plasmodium berghei infection. These compounds represent promising starting points for the development of novel antimalarial drugs. Crown Copyright (C) 2018 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.10.041
• 作为产物：
  描述：

  2-[2]naphthoyl-3-oxo-butyric acid ethyl ester 在 sodium methylate 、 sodium ethanolate 作用下， 生成 2-mercapto-6-(naphthalen-2-yl)pyrimidin-4(3H)-one
  参考文献：
  名称：

  Libermann et al., Bulletin de la Societe Chimique de France, 1950, p. 486,488

  摘要：

  DOI：

文献信息

• Synthesis of Chirally Enriched Pyrazolylpyrimidinone-Based Glycohybrids via Annulation of Glycals with 2-Hydrazineylpyrimidin-4(3<i>H</i>)-ones
  作者：Ghanshyam Tiwari、Vinay Kumar Mishra、Ashish Khanna、Rajdeep Tyagi、Ram Sagar

  DOI：10.1021/acs.joc.4c00211

  日期：2024.4.5

  A new strategy for synthesizing chirally enriched pyrazolylpyrimidinone-based glycohybrids has been achieved, employing an annulation approach in ethanol without any additives or catalysts under microwave conditions. The designed compounds were obtained within a short reaction time (5 min). This method offers several advantages, including mild reaction conditions, a green solvent, and a metal-free

  已经实现了一种合成手性富集的吡唑基嘧啶酮基糖杂化物的新策略，在微波条件下采用乙醇中的成环方法，无需任何添加剂或催化剂。设计的化合物在很短的反应时间内（5分钟）获得。该方法具有多种优点，包括温和的反应条件、绿色溶剂和无金属方法。此外，该方案展示了广泛的底物范围，成功地结合了具有立体化学多样性的各种官能团并提供了手性富集的分子。
• Identification of novel quinazoline derivatives as potent antiplasmodial agents
  作者：Anne Bouchut、Dante Rotili、Christine Pierrot、Sergio Valente、Sophia Lafitte、Johan Schultz、Urban Hoglund、Roberta Mazzone、Alessia Lucidi、Giancarlo Fabrizi、Dany Pechalrieu、Paola B. Arimondo、Tina S. Skinner-Adams、Ming Jang Chua、Kathy T. Andrews、Antonello Mai、Jamal Khalife

  DOI：10.1016/j.ejmech.2018.10.041

  日期：2019.1

  Despite the recent reductions in the global burden of malaria, this disease remains a devastating cause of death in tropical and subtropical regions. As there is no broadly effective vaccine for malaria, prevention and treatment still rely on chemotherapy. Unfortunately, emerging resistance to the gold standard artemisinin combination therapies means that new drugs with novel modes of action are urgently needed. In this context, Plasmodium histone modifying enzymes have emerged as potential drug targets, prompting us to develop and optimize compounds directed against such epigenetic targets. A panel of 51 compounds designed to target different epigenetic enzymes were screened for activity against Plasmodium falciparum parasites. Based on in vitro activity against drug susceptible and drug-resistant P. falciparum lines, selectivity index criterion and favorable pharmacokinetic properties, four compounds, one HDAC inhibitor (1) and three DNMT inhibitors (37,43 and 45), were selected for preclinical studies in a mouse model of malaria. In vivo data showed that 37, 43 and 45 exhibited oral efficacy in the mouse model of Plasmodium berghei infection. These compounds represent promising starting points for the development of novel antimalarial drugs. Crown Copyright (C) 2018 Published by Elsevier Masson SAS. All rights reserved.
• Libermann et al., Bulletin de la Societe Chimique de France, 1950, p. 486,488
  作者：Libermann et al.

  DOI：——

  日期：——