1-(5-Butyl-pyrazin-2-yl)-ethanone | 182306-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-Butyl-pyrazin-2-yl)-ethanone
• CAS: 182306-63-4
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: QFWAQBRANLRJRO-UHFFFAOYSA-N

物化性质

• 沸点：
  288.1±40.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.85
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(5-Butyl-pyrazin-2-yl)-ethanone 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-butylpyrazin-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-Butyl-pyrazine-2-carbonitrile 以 乙醚 为溶剂， 反应 1.0h， 以56%的产率得到1-(5-Butyl-pyrazin-2-yl)-ethanone
  参考文献：
  名称：

  5-Alkyl-2-pyrazinecarboxamides, 5-Alkyl-2-pyrazinecarbonitriles and 5-Alkyl-2-acetylpyrazines as Synthetic Intermediates for Antiinflammatory Agents

  摘要：

  2-吡啶基腈，2-乙酰吡嗪，5-烷基-2-吡嗪羧酰胺，5-烷基-2-吡嗪腈和5-烷基-2-乙酰吡嗪被制备为合成潜在抗炎药物的中间体。将吡啶羧酰胺的自由基烷基化结果与已发表的数据进行了比较。2-乙酰吡嗪及其5-(1,1-二甲基乙基)衍生物被筛选用于生物活性，但未发现有趣的效果。

  DOI：

  10.1135/cccc19961093

文献信息

• Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs
  作者：Marta Kucerova-Chlupacova、Veronika Vyskovska-Tyllova、Lenka Richterova-Finkova、Jiri Kunes、Vladimir Buchta、Marcela Vejsova、Pavla Paterova、Lucia Semelkova、Ondrej Jandourek、Veronika Opletalova

  DOI：10.3390/molecules21111421

  日期：——

  tested in vitro on antifungal and antimycobacterial activity. The highest potency was exhibited by derivatives with electron withdrawing groups (EWG) in positions 2 and 4 of the ring B. As halogens also have electron withdrawing properties, novel halogenated derivatives were prepared by Claisen-Schmidt condensation. All compounds were submitted for evaluation of their antifungal and antibacterial activity

  查耳酮，即具有1,3-二苯基丙-2-烯-1-酮化学模式的化合物，具有广泛的生物活性，例如抗氧化剂，抗炎剂，抗癌剂，抗感染剂等。该小组一直专注于查耳酮的吡嗪类似物；已经合成了多个系列并在体外测试了其抗真菌和抗分枝杆菌活性。在环B的2和4位带有吸电子基团（EWG）的衍生物表现出最高的效力。由于卤素也具有吸电子性能，因此通过Claisen-Schmidt缩合反应制备了新型卤代衍生物。所有化合物均已提交以评估其抗真菌和抗菌活性，包括其抗分枝杆菌作用。在针对八种选定真菌的抗真菌试验中，带有2-溴或2-氯取代的非烷基化衍生物显示了光滑念珠菌和叉毛癣菌（原指发癣菌）的生长抑制。在选定的细菌中，2-氯衍生物对葡萄球菌具有最高的抑制作用。此外，还针对所有产品筛选了针对结核分枝杆菌H37RV My 331/88，堪萨斯分枝杆菌My 235/80，鸟分枝杆菌152/80和耻垢分枝杆菌CCM 4622的抗分枝杆菌
• 5-Alkyl-2-pyrazinecarboxamides, 5-Alkyl-2-pyrazinecarbonitriles and 5-Alkyl-2-acetylpyrazines as Synthetic Intermediates for Antiinflammatory Agents
  作者：Veronika Opletalová、Asmita Patel、Michael Boulton、Alice Dundrová、Eva Lacinová、Marta Převorová、Martina Appeltauerová、Milada Coufalová

  DOI：10.1135/cccc19961093

  日期：——

  2-Pyrazinecarbonitrile, 2-acetylpyrazine, 5-alkyl-2-pyrazinecarboxamides, 5-alkyl-2-pyrazinecarbonitriles and 5-alkyl-2-acetylpyrazines were prepared as intermediates for use in synthesis of potential antiinflammatory agents. The results of the homolytic alkylation of pyrazinecarboxamide were compared with published data. 2-Acetylpyrazine and its 5-(1,1-dimethylethyl) derivative were screened for biological activity, but no interesting effect was found.

  2-吡啶基腈，2-乙酰吡嗪，5-烷基-2-吡嗪羧酰胺，5-烷基-2-吡嗪腈和5-烷基-2-乙酰吡嗪被制备为合成潜在抗炎药物的中间体。将吡啶羧酰胺的自由基烷基化结果与已发表的数据进行了比较。2-乙酰吡嗪及其5-(1,1-二甲基乙基)衍生物被筛选用于生物活性，但未发现有趣的效果。
• Synthesis and Biological Evaluation of (E)-3-(Nitrophenyl)-1-(pyrazin-2-yl)prop-2-en-1-ones
  作者：Veronika Opletalová、Milan Pour、Jiří Kuneš、Vladimír Buchta、Luís Silva、Katarína Kráľová、Marta Chlupáčová、Dana Meltrová、Milan Peterka、Martina Posledníková

  DOI：10.1135/cccc20060044

  日期：——

  The title (E)-(3-nitrophenyl)-1-(pyrazin-2-yl)prop-2-en-1-ones were prepared by the Claisen- Schmidt condensation of acetylpyrazines and 2-nitro-, 3-nitro- and 4-nitrobenzaldehyde in pyridine using diethylamine as the catalyst. The compounds were bioassayed for in vitro antifungal, antimycobacterial and photosynthesis-inhibiting activity. The high potency of (E)-1-(5-tert-butylpyrazin-2-yl)-3-(4-nitrophenyl)prop-2-en-1-one againstMycobacterium tuberculosis(MIC 0.78 μg/ml) and moderate activities of several compounds againstTrichophyton mentagrophytesandCandidaspp. do not support the assumption that phenolic groups are essential for antimycobacterial and antifungal activity of chalcones and their analogues. In fact, the nitro-substituted compounds were superior to the previously described hydroxylated congeners with antimycobacterial activity (MIC ≥ 12.5 μg/ml). The compounds also reduced chlorophyll content in green algaChlorella vulgaris, and some of them inhibited photosynthetic electron transport in spinach chloroplasts as well. The photosynthesis-inhibiting activity of nitro derivatives was lower than that of the corresponding hydroxylated analogues.

  标题：通过使用2-硝基、3-硝基和4-硝基苯甲醛与乙酰吡嗪在吡啶中以二乙胺为催化剂进行克莱森-施密特缩合反应合成了(E)-(3-硝基苯基)-1-(吡唑-2-基)丙烯酮。这些化合物进行了体外抗真菌、抗结核分枝杆菌和抑制光合作用的生物测定。其中(E)-1-(5-叔丁基吡唑-2-基)-3-(4-硝基苯基)丙烯酮对结核分枝杆菌具有高效抑制作用（最小抑菌浓度为0.78μg/ml），而一些化合物对白色念珠菌和癣菌具有中等活性。这表明酚类基团并非chalcones及其类似物的抗真菌和抗结核分枝杆菌活性所必需。实际上，硝基取代的化合物优于具有抗结核分枝杆菌活性的羟基化同系物（最小抑菌浓度≥12.5μg/ml）。这些化合物还可以减少绿藻Chlorella vulgaris的叶绿素含量，并且其中一些化合物还能抑制菠菜叶绿体中的光合电子传递。硝基衍生物的光合作用抑制活性低于相应的羟基化类似物。
• Ring substituted 3-phenyl-1-(2-pyrazinyl)-2-propen-1-ones as potential photosynthesis-inhibiting, antifungal and antimycobacterial agents
  作者：Veronika Opletalová、Jiřı́ Hartl、Asmita Patel、Karel Palát、Vladimı́r Buchta

  DOI：10.1016/s0014-827x(01)01187-9

  日期：2002.2

  Four series of ring substituted (E)-3-phenyl-1-(2-pyrazinyl)-2-propen-1-ones were prepared by means of modified Claisen-Schmidt condensation of acetylpyrazines with aromatic aldehydes. The structures were confirmed by elemental analysis, IR, H-1 NMR and C-13 NMR spectra. The compounds were tested for specific biological properties and some derivatives exhibited photosynthesis-inhibiting, antifungal and antimycobacterial properties. The most pronounced effects were observed with compounds substituted with phenolic groups. Ortho-hydroxyl substituted derivatives were more potent than the corresponding para-hydroxyl substituted analogues. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Study of hydrophobic properties of biologically active open analogues of flavonoids
  作者：Veronika Opletalová、Petr Kastner、Marta Kučerová-Chlupáčová、Karel Palát

  DOI：10.1016/j.jmgm.2012.07.009

  日期：2013.2

  Hydrophobicity can either be determined experimentally or predicted by means of commercially available programs. In the studies concerning biological activities of pyrazine analogues of chalcones, 3-(2-hydroxyphenyl)-1-(pyrazin-2-yl)prop-2-en-1-ones were more potent than the corresponding 3(4-hydroxyphenyl)-1-(pyrazin-2-yl)prop-2-en-1-ones. As the difference in lipophilicity may be a factor responsible for the difference in the potency, R-M values of the compounds were determined by RP-TLC and compared with log P values calculated by various commercially available programs. Important discrepancies were found between experimental and computational lipophilicity data. Therefore, we have tried to find a reliable method for calculating R-M values from in silico derived molecular parameters. The R-M values obtained with the chromatographic system consisting of Silufol UV 254 plates impregnated with silicon oil as the stationary phase and acetone-citrate buffer ( pH = 3)50:50 (v/v) as the mobile phase correlated well with van der Waals volumes (V-W) and hydration energies (Delta G(H2O)) derived of molecular models calculated on RHF/AM1 level. (C) 2012 Elsevier Inc. All rights reserved.