3-(phenylsulfonyl)pyrazine-2-carbonitrile | 74002-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(phenylsulfonyl)pyrazine-2-carbonitrile
• 英文别名: 3-benzenesulfonylpyrazine-2-carbonitrile；3-phenylsulfonylpyrazinecarbonitrile；3-(phenylsulfonyl)-2-pyrazinecarbonitrile；3-benzenesulfonyl-pyrazine-2-carbonitrile；3-(benzenesulfonyl)pyrazine-2-carbonitrile
• CAS: 74002-68-9
• 化学式: C₁₁H₇N₃O₂S
• 分子量: 245.261
• InChiKey: VGUOAQYMXUDOTB-UHFFFAOYSA-N

物化性质

• 熔点：
  103-105 °C(Solv: ethanol (64-17-5))
• 沸点：
  502.3±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(phenylsulfonyl)pyrazine-2-carbonitrile 在 六氯乙烷 、 sodium methylate 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 50.0h， 生成 3-methoxy-2-phenylpyrazino[2',3':4,5]thieno[3,2-d]-pyrimidin-4(3H)-one
  参考文献：
  名称：

  通过串联氮杂-维蒂希/杂异丙苯介导的环化策略合成吡嗪并[2'，3'：4,5]噻吩并[3,2- d ]嘧啶酮的实用一锅法

  摘要：

  描述了一种简单的一锅高效方法，该方法可通过aza-Wittig /杂异丙苯介导的环空法合成吡嗪并[2'，3'：4,5]噻吩并[3,2- d ]嘧啶酮衍生物6。亚氨基磷烷3与芳基异氰酸酯反应，然后通过添加仲胺进行杂环化，得到相应的胍中间体5，在催化量的碳酸钾存在下将其环化成三环化合物6。类似地，亚氨基磷烷3与酚，苯硫酚或ROH反应生成2-芳基（烷基）氧基（硫代）吡嗪并[2'，3'：4,5]噻吩并[3,2- d ]嘧啶酮衍生物7丰产。可以分离和表征相应的碳二亚胺4c和胍型中间体化合物5，从而证实了建议的反应途径。然而，在亚氨基磷烷3与芳族异氰酸酯的反应中，以及随后在催化量的碳酸钾的存在下，与伯胺的反应中，可以产生两种异构的吡嗪并噻吩并嘧啶酮8和9。研究了亲核试剂和异氰酸酯对环化区域选择性的影响。

  DOI：

  10.1016/j.tet.2006.09.028
• 作为产物：
  描述：

  2-氯-3-氰基吡嗪 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 3-(phenylsulfonyl)pyrazine-2-carbonitrile
  参考文献：
  名称：

  Antibacterial properties of 3-(phenylsulfonyl)-2-pyrazinecarbonitrile

  摘要：

  The emergence of multidrug-resistant bacterial strains has heightened the need for new antimicrobial agents based on novel chemical scaffolds that are able to circumvent current modes of resistance. We recently developed a whole-animal drug-screening methodology in pursuit of this goal and now report the discovery of 3-(phenylsulfonyl)-2-pyrazinecarbonitrile (PSPC) as a novel antibacterial effective against resistant nosocomial pathogens. The minimum inhibitory concentrations (MIC) of PSPC against Staphylococcus aureus and Enterococcus faecium were 4 mu g/mL and 8 mu g/mL, respectively, whereas the MICs were higher against the Gram-negative bacteria Klebsiella pneumoniae (64 mu g/mL), Acinetobacter baumannii (32 mu g/mL), Pseudomonas aeruginosa (>64 mu g/mL), and Enterobacter spp. (>64 mu g/mL). However, co-treatment of PSPC with the efflux pump inhibitor phenylalanine arginyl beta-naphthylamide (PA beta N) or with sub-inhibitory concentrations of the lipopeptide antibiotic polymyxin B reduced the MICs of PSPC against the Gram-negative strains by >4-fold. A sulfide analog of PSPC (PSPC-1S) showed no antibacterial activity, whereas the sulfoxide analog (PSPC-6S) showed identical activity as PSPC across all strains, confirming structure-dependent activity for PSPC and suggesting a target-based mechanism of action. PSPC displayed dose dependent toxicity to both Caenorhabditis elegans and HEK-293 mammalian cells, culminating with a survival rate of 16% (100 mu g/mL) and 8.5% (64 mu g/mL), respectively, at the maximum tested concentration. However, PSPC did not result in hemolysis of erythrocytes, even at a concentration of 64 mu g/mL. Together these results support PSPC as a new chemotype suitable for further development of new antibiotics against Gram-positive and Gram-negative bacteria. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.066

文献信息

• Sato, Nobuhiro; Matsui, Nobuo, Journal of Heterocyclic Chemistry, 1992, vol. 29, p. 1689 - 1692
  作者：Sato, Nobuhiro、Matsui, Nobuo

  DOI：——

  日期：——
• PANCECHOWSKA-KSEPKO D.; SAWLEWICZ J.; SAMULSKA J.; JANOWIEC M., ACTA POL. PHARM., 1979, 36, NO 3, 289-294
  作者：PANCECHOWSKA-KSEPKO D.、 SAWLEWICZ J.、 SAMULSKA J.、 JANOWIEC M.

  DOI：——

  日期：——
• Sato Nobuhiro, Matsui Nobuo, J. Heterocycl. Chem., 29 (1992) N 7, S 1689-1692
  作者：Sato Nobuhiro, Matsui Nobuo

  DOI：——

  日期：——
• Exploration of BAY 11-7082 as a Potential Antibiotic
  作者：Victoria E. Coles、Patrick Darveau、Xiong Zhang、Hanjeong Harvey、Brandyn D. Henriksbo、Angela Yang、Jonathan D. Schertzer、Jakob Magolan、Lori L. Burrows

  DOI：10.1021/acsinfecdis.1c00522

  日期：2022.1.14
• Antibacterial properties of 3-(phenylsulfonyl)-2-pyrazinecarbonitrile
  作者：Rajmohan Rajamuthiah、Elamparithi Jayamani、Hiwa Majed、Annie L. Conery、Wooseong Kim、Bumsup Kwon、Beth Burgwyn Fuchs、Michael J. Kelso、Frederick M. Ausubel、Eleftherios Mylonakis

  DOI：10.1016/j.bmcl.2015.09.066

  日期：2015.11

  The emergence of multidrug-resistant bacterial strains has heightened the need for new antimicrobial agents based on novel chemical scaffolds that are able to circumvent current modes of resistance. We recently developed a whole-animal drug-screening methodology in pursuit of this goal and now report the discovery of 3-(phenylsulfonyl)-2-pyrazinecarbonitrile (PSPC) as a novel antibacterial effective against resistant nosocomial pathogens. The minimum inhibitory concentrations (MIC) of PSPC against Staphylococcus aureus and Enterococcus faecium were 4 mu g/mL and 8 mu g/mL, respectively, whereas the MICs were higher against the Gram-negative bacteria Klebsiella pneumoniae (64 mu g/mL), Acinetobacter baumannii (32 mu g/mL), Pseudomonas aeruginosa (>64 mu g/mL), and Enterobacter spp. (>64 mu g/mL). However, co-treatment of PSPC with the efflux pump inhibitor phenylalanine arginyl beta-naphthylamide (PA beta N) or with sub-inhibitory concentrations of the lipopeptide antibiotic polymyxin B reduced the MICs of PSPC against the Gram-negative strains by >4-fold. A sulfide analog of PSPC (PSPC-1S) showed no antibacterial activity, whereas the sulfoxide analog (PSPC-6S) showed identical activity as PSPC across all strains, confirming structure-dependent activity for PSPC and suggesting a target-based mechanism of action. PSPC displayed dose dependent toxicity to both Caenorhabditis elegans and HEK-293 mammalian cells, culminating with a survival rate of 16% (100 mu g/mL) and 8.5% (64 mu g/mL), respectively, at the maximum tested concentration. However, PSPC did not result in hemolysis of erythrocytes, even at a concentration of 64 mu g/mL. Together these results support PSPC as a new chemotype suitable for further development of new antibiotics against Gram-positive and Gram-negative bacteria. (C) 2015 Elsevier Ltd. All rights reserved.