1-(5-benzylpyrazin-2-yl)ethan-1-one | 916333-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-benzylpyrazin-2-yl)ethan-1-one
• 英文别名: 1-(5-Benzylpyrazin-2-yl)ethanone
• CAS: 916333-52-3
• 化学式: C₁₃H₁₂N₂O
• 分子量: 212.251
• InChiKey: SXJISEXZYPZXBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-benzylpyrazin-2-yl)ethan-1-one 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 15.0h， 生成 2-{[1-(5-benzylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-one
  参考文献：
  名称：

  2-{[1-（5-烷基/芳烷基吡嗪-2-基）亚乙基] hydr] -1,3-噻唑烷-4-酮的合成及抗真菌筛选。

  摘要：

  制备了两个新颖的硫代半氨基甲酮和八个新颖的2-{[1-（5-（烷基/芳基烷基吡嗪-2-基）亚乙基] hydr] -1,3-噻唑烷-4-酮，并针对一组八个真菌菌株-念珠菌进行了测试。白色念珠菌ATCC 44859，热带假丝酵母156，克鲁斯假丝酵母E 28，光滑假丝酵母20 / I，细毛Trichosporon asahii 1188，烟曲霉231，鳞翅目利什曼原虫272和指状毛癣菌445.1,3-噻唑烷酮4-对所有菌株均表现出活性。 ，最有效的衍生物是2-{[1-（1-（5-丁基吡嗪-2-基）亚乙基]肼基} e-1,3-噻唑烷丁-4-酮。由于这种机会性病原体对唑类的敏感度很低，因此变得很容易引起光滑念珠菌对研究的1,3-噻唑烷酮-4-酮（最低抑菌浓度（MIC）为0.57至2.78 mg / L）的敏感性。对棘霉素有抗性。

  DOI：

  10.3390/molecules21111592
• 作为产物：
  描述：

  甲基碘化镁 、 5-benzylpyrazine-2-carbonitrile 在 水 作用下， 以 乙醚 为溶剂， 生成 1-(5-benzylpyrazin-2-yl)ethan-1-one
  参考文献：
  名称：

  作为潜在药物的罗丹宁乙酸衍生物：（5-芳基亚烷基-4-氧代-2-硫代-1,3-噻唑烷-3-基）乙酸的制备、疏水特性和抗真菌活性。

  摘要：

  一些 [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)] 乙酸被制备为潜在的抗真菌化合物。介绍了所有合成化合物的通用合成方法。使用反相高效液相色谱 (RP-HPLC) 方法分析所有讨论过的罗丹宁-3-乙酸衍生物的亲脂性。该过程是在等度条件下使用甲醇作为流动相中的有机改性剂使用封端的非极性 C(18) 固定 RP 柱进行的。将 RP-HPLC 保留参数 log k（容量因子 k 的对数）与计算机计算的 log P 值进行比较。评估所有化合物对选定真菌物种的抗真菌作用。大多数化合物没有表现出有趣的活性，

  DOI：

  10.3390/molecules14104197

文献信息

• New Hydrophobicity Constants of Substituents in Pyrazine Rings Derived from RP-HPLC Study
  作者：Marta Kučerová-Chlupáčová、Veronika Opletalová、Josef Jampílek、Jan Doležel、Jiří Dohnal、Milan Pour、Jiří Kuneš、Viktor Voříšek

  DOI：10.1135/cccc20080001

  日期：——

  Pyrazine derivatives show a wide range of biological activities. 1-Pyrazin-2-ylethan-1-ones have served as food flavourants, and together with pyrazine-2-carbonitriles have been widely used as intermediates in the synthesis of various heterocyclic compounds. In our laboratory, substituted pyrazine-2-carbonitriles and 1-pyrazin-2-ylethan-1-ones have been used as intermediates for the preparation of potential antifungal and antimycobacterial drugs. Using established methods, a library of pyrazine derivatives was synthesized. Homolytic alkylation of commercially available pyrazine-2-carbonitrile yielded a series of 5-alkylpyrazine-2-carbonitriles which were converted into the corresponding 1-(5-alkylpyrazin-2-yl)ethan-1-ones (5-alkyl-2-acetylpyrazines) via the Grignard reaction. Homolytic acetylation of pyrazine-2-carbonitrile yielded 5-acetylpyrazine-2-carbonitrile. Using the same procedure, 3-acetyl-5-tert-butylpyrazine-2-carbonitrile was obtained with 5-tert-butylpyrazine-2-carbonitrile as a starting material. The hydrophobicity of the compounds was determined both experimentally (RP-HPLC) and by computation (CS ChemOffice Ultra version 9.0, ACD/LogP version 1.0 and ACD/LogP version 9.04), and both the approaches were compared. New hydrophobicity constants π based on experimental results were derived. These constants are markedly different from tabulated constants π valid for benzene rings, and can be widely used in estimating physicochemical properties of new biologically active pyrazines.

  吡嗪衍生物展示了广泛的生物活性。1-吡嗪-2-基乙酮已被用作食品香精，与吡嗪-2-碳腈一起被广泛用作合成各种杂环化合物的中间体。在我们的实验室中，取代吡嗪-2-碳腈和1-吡嗪-2-基乙酮已被用作潜在抗真菌和抗分枝杆菌药物的制备中间体。使用已建立的方法，合成了一系列吡嗪衍生物。商业可得的吡嗪-2-碳腈的自由基烷基化产生了一系列5-烷基吡嗪-2-碳腈，这些化合物通过格氏试剂反应转化为相应的1-(5-烷基吡嗪-2-基)乙酮（5-烷基-2-乙酰吡嗪）。吡嗪-2-碳腈的自由基乙酰化产生了5-乙酰吡嗪-2-碳腈。使用相同的程序，以5-叔丁基吡嗪-2-碳腈为起始物获得了3-乙酰-5-叔丁基吡嗪-2-碳腈。这些化合物的疏水性通过实验（RP-HPLC）和计算（CS ChemOffice Ultra版本9.0，ACD/LogP版本1.0和ACD/LogP版本9.04）确定，并进行了比较。基于实验结果得出了新的疏水性常数π。这些常数与对苯环有效的表格常数π明显不同，可以广泛用于估计新的生物活性吡嗪的物理化学性质。
• Compositions For Treating Flushing And Lipid-Associated Disorders Comprising Niacin Receptor Partial Agonists
  申请人：Behan Dominic P.

  公开号：US20080139628A1

  公开（公告）日：2008-06-12

  The invention provides a method of reducing flushing induced by niacin or a niacin analog in a subject, comprising administering to said subject an effective flush reducing amount of a niacin receptor partial agonist. In addition, the invention provides a method of reducing flushing induced by niacin or a niacin analog in a subject, comprising administering to said subject an effective flush reducing amount of a niacin receptor partial agonist and an effective lipid altering amount of niacin or a niacin analog. The invention further provides a method of reducing flushing induced by niacin or a niacin analog in a subject, comprising administering to said subject an effective flush reducing amount of a niacin receptor partial agonist and subsequently administering to said subject an effective lipid altering amount of niacin or a niacin analog.

  本发明提供了一种减少烟酸或烟酸类似物引起的面红的方法，包括向该受体中注射有效减少面红量的烟酸受体部分激动剂。此外，本发明还提供了一种减少烟酸或烟酸类似物引起的面红的方法，包括向该受体中注射有效减少面红量的烟酸受体部分激动剂和有效改变脂质含量的烟酸或烟酸类似物。本发明进一步提供了一种减少烟酸或烟酸类似物引起的面红的方法，包括向该受体中注射有效减少面红量的烟酸受体部分激动剂，然后向该受体中注射有效改变脂质含量的烟酸或烟酸类似物。
• Human G Protein-Coupled Receptors and Modulators Thereof for the Treatment of Metabolic-Related Disorders
  申请人：Unett David J.

  公开号：US20110177612A1

  公开（公告）日：2011-07-21

  The present invention relates to methods of identifying whether a candidate compound is a modulator of a G protein-coupled receptor (GPCR). In preferred embodiments, the GPCR is human. In other preferred embodiments, the GPCR is coupled to Gi and lowers the level of intracellular cAMP. In other preferred embodiments, the GPCR is expressed endogenously by adipocytes. In further preferred embodiments, the GPCR inhibits intracellular lipolysis. In other further preferred embodiments, the GPCR is a nicotinic acid receptor. The present invention also relates to methods of using a modulator of said GPCR. Preferred modulator is agonist. Agonists of the invention are useful as therapeutic agents for the prevention or treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, stroke, insulin resistance, and type 2 diabetes.
• Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation, Hydrophobic Properties and Antifungal Activity of (5-Arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic Acids
  作者：Jan Dolezel、Petra Hirsova、Veronika Opletalova、Jiri Dohnal、Vejsova Marcela、Jiri Kunes、Josef Jampilek

  DOI：10.3390/molecules14104197

  日期：——

  Some [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids were prepared as potential antifungal compounds. The general synthetic approach to all synthesized compounds is presented. Lipophilicity of all the discussed rhodanine-3-acetic acid derivatives was analyzed using a reversed phase high performance liquid chromatography (RP-HPLC) method. The procedure was performed under isocratic

  一些 [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)] 乙酸被制备为潜在的抗真菌化合物。介绍了所有合成化合物的通用合成方法。使用反相高效液相色谱 (RP-HPLC) 方法分析所有讨论过的罗丹宁-3-乙酸衍生物的亲脂性。该过程是在等度条件下使用甲醇作为流动相中的有机改性剂使用封端的非极性 C(18) 固定 RP 柱进行的。将 RP-HPLC 保留参数 log k（容量因子 k 的对数）与计算机计算的 log P 值进行比较。评估所有化合物对选定真菌物种的抗真菌作用。大多数化合物没有表现出有趣的活性，
• Synthesis and Antifungal Screening of 2-{[1-(5-Alkyl/arylalkylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-ones
  作者：Veronika Opletalova、Jan Dolezel、Jiri Kunes、Vladimir Buchta、Marcela Vejsova、Marta Kucerova-Chlupacova

  DOI：10.3390/molecules21111592

  日期：——

  interdigitale 445. 1,3-Thiazolidin-4-ones exhibited activity against all strains, the most potent derivative was 2-[1-(5-butylpyrazin-2-yl)ethylidene]hydrazono}e-1,3-thiazolidin-4-one. Susceptibility of C. glabrata to the studied 1,3-thiazolidin-4-ones (minimum inhibitory concentrations (MICs) were in the range 0.57 to 2.78 mg/L) is of great interest as this opportunistic pathogen is poorly susceptible to azoles

  制备了两个新颖的硫代半氨基甲酮和八个新颖的2-[1-（5-（烷基/芳基烷基吡嗪-2-基）亚乙基] hydr] -1,3-噻唑烷-4-酮，并针对一组八个真菌菌株-念珠菌进行了测试。白色念珠菌ATCC 44859，热带假丝酵母156，克鲁斯假丝酵母E 28，光滑假丝酵母20 / I，细毛Trichosporon asahii 1188，烟曲霉231，鳞翅目利什曼原虫272和指状毛癣菌445.1,3-噻唑烷酮4-对所有菌株均表现出活性。 ，最有效的衍生物是2-[1-（1-（5-丁基吡嗪-2-基）亚乙基]肼基} e-1,3-噻唑烷丁-4-酮。由于这种机会性病原体对唑类的敏感度很低，因此变得很容易引起光滑念珠菌对研究的1,3-噻唑烷酮-4-酮（最低抑菌浓度（MIC）为0.57至2.78 mg / L）的敏感性。对棘霉素有抗性。