4-Oxocyclohexanecarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Oxocyclohexanecarboxylate
• 英文别名: 4-oxocyclohexane-1-carboxylate
• 化学式: C7H9O3-
• 分子量: 141.14
• InChiKey: OWLXUYGCLDGHJJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-氯吡嗪-2-基)甲胺盐酸盐 、 三乙胺 、 O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate 、 4-Oxocyclohexanecarboxylate 在 二氯甲烷 、 水 、 Sodium sulfate-III 、 crude product 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以to afford 1.09 g of the title compound的产率得到N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamide
  参考文献：
  名称：

  8-METHYL-1-PHENYL-IMIDAZOL[1,5-A]PYRAZINE COMPOUNDS

  摘要：

  本发明提供了按式I或其药学上可接受的盐所表示的8-甲基-1-苯基咪唑[1,5-a]吡嗪衍生物。本发明的化合物显示出对Lck的抑制活性，并可用于治疗由Lck介导的疾病或Lck介导的炎症性疾病状态。

  公开号：

  US20120309966A1
• 作为产物：
  描述：

  nicotinamide adenine dinucleotide 、 trans-4-hydroxycyclohexanecarboxylate 生成 4-Oxocyclohexanecarboxylate 、 氢(+1)阳离子 、 NADH
  参考文献：
  名称：

  Purification and properties of 4-hydroxycyclohexanecarboxylate dehydrogenase from Corynebacterium cyclohexanicum

  摘要：

  4‐Hydroxycyclohexanecarboxylate dehydrogenase, which requires NAD as a cofactor, was detected in crude soluble extracts of Corynebacterium cyclohexanicum grown on cyclohexanecarboxylic acid as the sole carbon source. The dehydrogenase was purified from extracts to an electrophoretically homogenous state by ammonium sulfate precipitation and chromatography on DEAE‐650s, agarose‐NAD and hydroxyapatite. The enzyme consisted of two identical subunits and had a native relative molecular mass of 53600. There were two residues each of cysteine and tryptophan in the enzyme molecule. Oxo acid rather than hydroxy acid was routinely used as substrate for assay of the enzyme. The enzyme is highly specific for 4‐oxocyclohexanecarboxylic acid: the carboxyl group is essential and the position of carbonyl group is important; neither the 2‐oxo nor the 3‐oxo homologue was used as substrate. A methyl substitution on the ring of 4‐oxocyclohexanecarboxylate resulted in an almost complete loss of its activity. The reduction product was identified as trans‐4‐hydroxycyclohexanecarboxylic acid by gas‐liquid chromatography and mass spectrometry. It was used as a substrate for the reverse reaction in the presence of NAD but not its cis‐isomer. The enzyme was specific for the B‐side (pro‐S) hydrogen of NADH in the hydrogen transfer from NADH to 4‐oxocyclohexanecarboxylate. The Km, values for 4‐oxocyclohexanecarboxylate and NADH in the reduction reaction at pH 6.8 were 0.50 mM and 0.28 mM, respectively, whereas those for trans‐4 hydroxycyclohexanecarboxylate and NAD in the oxidation reaction at pH 8.8 were 0.51 mM and 0.23 mM, respectively. The equilibrium constant of the reaction was 1.79 × 10‐10M. The enzyme was strongly inhibited by N‐bromosuccinimide.

  DOI：

  10.1111/j.1432-1033.1988.tb14119.x

文献信息

• 8-methyl-1-phenyl-imidazol[1,5-a]pyrazine compounds as Lck inhibitors and uses thereof
  申请人：de Man Adrianus Petrus Antonius

  公开号：US08658794B2

  公开（公告）日：2014-02-25

  The present invention provides 8-methyl-1-phenyl-imidazo[1,5-a]pyrazine derivatives according to formula I or pharmaceutically acceptable salts thereof. The compounds of the current invention show inhibitory activity against Lck and can be used for the treatment of Lck-mediated diseases or Lck-mediated conditions such as inflammatory disorders.

  本发明提供了公式I所示的8-甲基-1-苯基咪唑并[1,5-a]吡嗪衍生物或其药学上可接受的盐。本发明的化合物显示出对Lck的抑制活性，可用于治疗Lck介导的疾病或Lck介导的病状，如炎症性疾病。