10-propylbenzo[g]pteridine-2,4(3H,10H)-dione | 46965-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 10-propylbenzo[g]pteridine-2,4(3H,10H)-dione
• 英文别名: 10-propyl-10H-benzo[g]pteridine-2,4-dione；10-Propyl-10H-benzo[g]pteridin-2,4-dion；10-n-Propylisoalloxazin；10-Propylbenzo[g]pteridine-2,4(3H,10H)-dione (7a)；10-propylbenzo[g]pteridine-2,4-dione
• CAS: 46965-08-6
• 化学式: C₁₃H₁₂N₄O₂
• 分子量: 256.264
• InChiKey: PHYAHGOFTLKBQO-UHFFFAOYSA-N

物化性质

• 熔点：
  349 °C
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-溴辛烷 、 10-propylbenzo[g]pteridine-2,4(3H,10H)-dione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78 %的产率得到
  参考文献：
  名称：

  通过肽附属物稳定氢过氧黄素中间体的形成：中性黄素酶模型

  摘要：

  设计了一种用于稳定氢过氧黄素中间体形成的仿生模拟物，并研究了单加氧酶的催化特性。将合适的肽附件共价连接到中性异恶嗪核心的 C7 位，以合成Fl-G、Fl-F、Fl-P和Fl-βA类似物。虽然发现肽附件的存在和特性对催化效率至关重要，但理论研究也做出了确凿的观察，支持稳定关键氢过氧黄素中间体的精确构象和可及性要求。一个简单而优雅的黄肽模型（Fl-G) 与没有肽附属物的对照黄素类似物相比，发现几乎可以实现定量催化效率。

  DOI：

  10.1039/d3ob00125c
• 作为产物：
  描述：

  N-2-硝基苯基丙胺 在 硼酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 生成 10-propylbenzo[g]pteridine-2,4(3H,10H)-dione
  参考文献：
  名称：

  Discovery of isoalloxazine derivatives as a new class of potential anti-Alzheimer agents and their synthesis

  摘要：

  This article describes discovery of a novel and new class of cholinesterase inhibitors as potential therapeutics for Alzheimer's disease. A series of novel isoalloxazine derivatives were synthesized and biologically evaluated for their potential inhibitory outcome for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). These compounds exhibited high activity against both the enzymes AChE as well as BuChE. Of the synthesized compounds, the most potent isoalloxazine derivatives (7m and 7q) showed IC50 values of 4.72 mu M and 5.22 mu M respectively against AChE; and, 6.98 mu M and 5.29 mu M respectively against BuChE. These two compounds were further evaluated for their anti-aggregatory activity for beta-amyloid (A beta) in presence and absence of AChE by performing Thioflavin-T (ThT) assay and Congo red (CR) binding assay. In order to evaluate cytotoxic profile of these two potential compounds, cell viability assay of SH-SY5Y human neuroblastoma cells was performed. Further, to understand the binding behavior of these two compounds with AChE and BuChE enzymes, docking studies have been reported. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.05.005

文献信息

• Flavin based supramolecular gel displaying multi-stimuli triggered sol–gel transition
  作者：M. S. S. Vinod Mouli、Ashutosh Kumar Mishra

  DOI：10.1039/d3ob00720k

  日期：——

  report the design and synthesis of an amphiphilic flavin analogue as a robust low molecular weight gelator involving minimal structural modification. Four flavin analogues were evaluated for their gelation capabilities and the flavin analogue with antipodal positioning of the carboxyl and octyl functionalities was found to be the most efficient gelator with the minimum gelation concentration being as

  在此，我们报告了两亲性黄素类似物的设计和合成，作为一种稳健的低分子量胶凝剂，涉及最小的结构修饰。对四种黄素类似物的胶凝能力进行了评估，发现具有羧基和辛基官能团对映位置的黄素类似物是最有效的胶凝剂，其最小胶凝浓度低至 0.03 M。凝胶化研究表明其广泛的适用性。进行了形态学、光物理和流变学表征研究，以充分表征凝胶的性质。有趣的是，随着 pH 值和氧化还原活性的变化，观察到可逆的多重刺激响应溶胶-凝胶转变，而金属筛选则在铁离子存在下显示出特异性转变。该凝胶能够通过明确的溶胶-凝胶转变区分铁和亚铁物质。目前的结果有可能为下一代材料的开发提供一种氧化还原活性黄素基材料作为低分子量胶凝剂。
• Hemmerich et al., Angewandte Chemie, 1965, vol. 77, p. 699; int. Ed. 4<1965>671
  作者：Hemmerich et al.

  DOI：——

  日期：——
• YONEDA F.; SAKUMA Y., HETEROCYCLES, 1977, 6, NO 1, 25-28
  作者：YONEDA F.、 SAKUMA Y.

  DOI：——

  日期：——
• Discovery of isoalloxazine derivatives as a new class of potential anti-Alzheimer agents and their synthesis
  作者：Ashish M. Kanhed、Anshuman Sinha、Jatin Machhi、Ashutosh Tripathi、Zalak S. Parikh、Prakash P. Pillai、Rajani Giridhar、Mange Ram Yadav

  DOI：10.1016/j.bioorg.2015.05.005

  日期：2015.8

  This article describes discovery of a novel and new class of cholinesterase inhibitors as potential therapeutics for Alzheimer's disease. A series of novel isoalloxazine derivatives were synthesized and biologically evaluated for their potential inhibitory outcome for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). These compounds exhibited high activity against both the enzymes AChE as well as BuChE. Of the synthesized compounds, the most potent isoalloxazine derivatives (7m and 7q) showed IC50 values of 4.72 mu M and 5.22 mu M respectively against AChE; and, 6.98 mu M and 5.29 mu M respectively against BuChE. These two compounds were further evaluated for their anti-aggregatory activity for beta-amyloid (A beta) in presence and absence of AChE by performing Thioflavin-T (ThT) assay and Congo red (CR) binding assay. In order to evaluate cytotoxic profile of these two potential compounds, cell viability assay of SH-SY5Y human neuroblastoma cells was performed. Further, to understand the binding behavior of these two compounds with AChE and BuChE enzymes, docking studies have been reported. (C) 2015 Elsevier Inc. All rights reserved.
• Stabilizing hydroperoxyflavin intermediate formation <i>via</i> a peptide appendage: a neutral flavoenzyme model
  作者：M. S. S. Vinod Mouli、Dipayan Mondal、Kusum Kumari、Saurabh Kumar Singh、Ashutosh Kumar Mishra

  DOI：10.1039/d3ob00125c

  日期：——

  for the stabilization of hydroperoxyflavin intermediate formation was designed and investigated for monooxygenase like catalytic properties. A suitable peptide appendage was covalently linked to the C7-position of the neutral isoalloxazine core to synthesize Fl-G, Fl-F, Fl-P, and Fl-βA analogues. While the presence and identity of the peptide appendage were found to be crucial for catalytic efficiency

  设计了一种用于稳定氢过氧黄素中间体形成的仿生模拟物，并研究了单加氧酶的催化特性。将合适的肽附件共价连接到中性异恶嗪核心的 C7 位，以合成Fl-G、Fl-F、Fl-P和Fl-βA类似物。虽然发现肽附件的存在和特性对催化效率至关重要，但理论研究也做出了确凿的观察，支持稳定关键氢过氧黄素中间体的精确构象和可及性要求。一个简单而优雅的黄肽模型（Fl-G) 与没有肽附属物的对照黄素类似物相比，发现几乎可以实现定量催化效率。