2-苄基-3-氯吡嗪 | 57693-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-苄基-3-氯吡嗪
• 英文名称: 2-benzyl-3-chloropyrazine
• 英文别名: Pyrazine, 2-chloro-3-(phenylmethyl)-
• CAS: 57693-15-9
• 化学式: C₁₁H₉ClN₂
• 分子量: 204.659
• InChiKey: ZBOJSNPGBJMUSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苄基-3-氯吡嗪 在 间氯过氧苯甲酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 15.0h， 以75%的产率得到3-benzyl-2-chloropyrazine 4-oxide
  参考文献：
  名称：

  抗球虫药。V.2（1H）-吡嗪酮4-氧化物衍生物的合成和抗球虫活性。

  摘要：

  合成了一系列1-、3-、5-和6取代的2(1H)-吡咯啉酮4-氧化物，并测试其抗球虫活性。在测试的化合物中，1-(β-D-核糖苷)-(22)、1-(2, 3, 5-三-O-苯甲酰-β-D-核糖苷)-(21)和1-(2, 3, 5-三-O-乙酰-β-D-核糖苷)-2(1H)-吡咯啉酮4-氧化物(24)显示出较高的活性。

  DOI：

  10.1248/cpb.28.2734
• 作为产物：
  描述：

  2,3-二氯吡嗪 、 2-苄基-4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以100%的产率得到2-苄基-3-氯吡嗪
  参考文献：
  名称：

  Discovery of a Type III Inhibitor of LIM Kinase 2 That Binds in a DFG-Out Conformation

  摘要：

  The first allosteric, type III inhibitor of LIM-kinase 2 (LIMK2) is reported. A series of molecules that feature both an N-phenylsulfonamide and tertiary amide were not only very potent at LIMK2 but also were extremely selective against a panel of other kinases. Enzymatic kinetic studies showed these molecules to be noncompetitive with ATP, suggesting allosteric inhibition. X-ray crystallography confirmed that these sulfonamides are a rare example of a type III kinase inhibitor that binds away from the highly conserved hinge region and instead resides in the hydrophobic pocket formed in the DFG-out conformation of the kinase, thus accounting for the high level of selectivity observed.

  DOI：

  10.1021/ml500242y

文献信息

• MANO MITSUHIKO; SEO TAKUJI; HATTORI TOSHINORI; KANEKO TATSUHIKO; IMAI KIN+, CHEM. AND PHARM. BULL., 1980, 28, NO 9, 2734-2747
  作者：MANO MITSUHIKO、 SEO TAKUJI、 HATTORI TOSHINORI、 KANEKO TATSUHIKO、 IMAI KIN+

  DOI：——

  日期：——
• Anticoccidials. V. Synthesis and anticoccidial activity of 2(1H)-pyrazinone 4-oxide derivatives.
  作者：MITSUHIKO MANO、TAKUJI SEO、TOSHINORI HATTORI、TATSUHIKO KANEKO、KINICHI IMAI

  DOI：10.1248/cpb.28.2734

  日期：——

  A series of 1-, 3-, 5- and 6-substituted 2(1H)-pyrazinone 4-oxides were synthesized and tested for anticoccidial activity. Of the compounds tested, 1-(β-D-ribofuranosyl)-(22), 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl)-(21) and 1-(2, 3, 5-tri-O-acetyl-β-D-ribofuranosyl)-2(1H)-pyrazinone 4-oxides (24) showed high activity.

  合成了一系列1-、3-、5-和6取代的2(1H)-吡咯啉酮4-氧化物，并测试其抗球虫活性。在测试的化合物中，1-(β-D-核糖苷)-(22)、1-(2, 3, 5-三-O-苯甲酰-β-D-核糖苷)-(21)和1-(2, 3, 5-三-O-乙酰-β-D-核糖苷)-2(1H)-吡咯啉酮4-氧化物(24)显示出较高的活性。
• Discovery of a Type III Inhibitor of LIM Kinase 2 That Binds in a DFG-Out Conformation
  作者：Nicole C. Goodwin、Giovanni Cianchetta、Hugh A. Burgoon、Jason Healy、Ross Mabon、Eric D. Strobel、Jason Allen、Shuli Wang、Brian D. Hamman、David B. Rawlins

  DOI：10.1021/ml500242y

  日期：2015.1.8

  The first allosteric, type III inhibitor of LIM-kinase 2 (LIMK2) is reported. A series of molecules that feature both an N-phenylsulfonamide and tertiary amide were not only very potent at LIMK2 but also were extremely selective against a panel of other kinases. Enzymatic kinetic studies showed these molecules to be noncompetitive with ATP, suggesting allosteric inhibition. X-ray crystallography confirmed that these sulfonamides are a rare example of a type III kinase inhibitor that binds away from the highly conserved hinge region and instead resides in the hydrophobic pocket formed in the DFG-out conformation of the kinase, thus accounting for the high level of selectivity observed.