2-amino-5-chloro-3-cyano-6-(methylthio)pyrazine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-amino-5-chloro-3-cyano-6-(methylthio)pyrazine
• 英文别名: 3-amino-6-chloro-5-methylsulfanylpyrazine-2-carbonitrile
• 化学式: C₆H₅ClN₄S
• 分子量: 200.651
• InChiKey: SZMCILPTSHSVRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-5-chloro-3-cyano-6-(methylthio)pyrazine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-(aminomethyl)-5-chloro-6-methylsulfanylpyrazin-2-amine
  参考文献：
  名称：

  Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas as potent inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas are described as inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2). These compounds demonstrate potent in vitro activity against the enzyme with IC50 values as low as 15 nM, and suppress expression of TNF alpha in THP-1 cells and in vivo in an acute inflammation model in mice. The synthesis, structure-activity relationship (SAR), and biological evaluation of these compounds are discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.088
• 作为产物：
  描述：

  3-氨基-5,6-二氯吡嗪-2-甲腈 生成 2-amino-5-chloro-3-cyano-6-(methylthio)pyrazine
  参考文献：
  名称：

  JOHNSTON, D. B. R.

  摘要：

  DOI：

文献信息

• 2-Amino-3-cyano-5-halo-6-(substituted)pyrazine
  申请人：Merck & Co., Inc.

  公开号：US04518599A1

  公开（公告）日：1985-05-21

  Antimicrobial compounds of the formula: ##STR1## wherein: Hal is bromine or chlorine; and R is mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C.sub.1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; are useful in various agricultural and industrial areas.

  该化合物的抗微生物化合物的公式为：##STR1## 其中：Hal是溴或氯；R是单取代或双取代的单取代或双取代低烷基氨基，其中低烷基取代基是羟基或低烷酰氧基；4-吗啉基；硫氰基；巯基；直链或支链C.sub.1-8烷基硫基；单取代或双取代的低烷基硫基，其中取代基是羟基，氨基，低烷酰胺基或低烷氧羰基；芳基硫基；低烷基磺酸氧基；或低烷基磺酰基；在各种农业和工业领域中是有用的。
• JOHNSTON, D. B. R.
  作者：JOHNSTON, D. B. R.

  DOI：——

  日期：——
• US4518599A
  申请人：——

  公开号：US4518599A

  公开（公告）日：1985-05-21
• Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas as potent inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2)
  作者：Songnian Lin、Matthew Lombardo、Sunita Malkani、Jeffrey J. Hale、Sander G. Mills、Kevin Chapman、James E. Thompson、Wen Xiao Zhang、Ruixiu Wang、Rose M. Cubbon、Edward A. O’Neill、Silvi Luell、Ester Carballo-Jane、Lihu Yang

  DOI：10.1016/j.bmcl.2009.04.088

  日期：2009.6

  Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas are described as inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2). These compounds demonstrate potent in vitro activity against the enzyme with IC50 values as low as 15 nM, and suppress expression of TNF alpha in THP-1 cells and in vivo in an acute inflammation model in mice. The synthesis, structure-activity relationship (SAR), and biological evaluation of these compounds are discussed. (C) 2009 Elsevier Ltd. All rights reserved.