(S)-4-Oxo-1,2,3,4-tetrahydro-pyridine-2,6-dicarboxylic acid 6-ethyl ester 2-methyl ester | 316802-58-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-4-Oxo-1,2,3,4-tetrahydro-pyridine-2,6-dicarboxylic acid 6-ethyl ester 2-methyl ester
• CAS: 316802-58-1
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: QRAWJRWOECKVLJ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-4-Oxo-1,2,3,4-tetrahydro-pyridine-2,6-dicarboxylic acid 6-ethyl ester 2-methyl ester 在 lithium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 17.0h， 以90%的产率得到(2S)-4-oxo-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid
  参考文献：
  名称：

  Vinylogous Amide Analogues of Diaminopimelic Acid (DAP) as Inhibitors of Enzymes Involved in Bacterial Lysine Biosynthesis

  摘要：

  [GRAPHICS]Vinylogous amides 5 and 6 have been synthesized from L-propargyl glycine and tested against diaminopimelate (DAP) enzymes involved in bacterial lysine biosynthesis, Both are reversible inhibitors of DAP D-dehydrogenase and DAP epimerase with IC50 values in the 500 muM range, Compound 5 shows competitive inhibition against the L-dihydrodipicolinate (DHDP) reductase with a K-i value of 32 muM, which is comparable to the planar dipicolinate 16 (K-i = 26 muM), the best known inhibitor of the enzyme.

  DOI：

  10.1021/ol000271e
• 作为产物：
  描述：

  (2S)-2-[[叔丁氧羰基]氨基]-4-戊炔酸酸甲酯 在 molybdenum hexacarbonyl 、 水 、 sodium carbonate 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 12.0h， 生成 (S)-4-Oxo-1,2,3,4-tetrahydro-pyridine-2,6-dicarboxylic acid 6-ethyl ester 2-methyl ester
  参考文献：
  名称：

  Vinylogous Amide Analogues of Diaminopimelic Acid (DAP) as Inhibitors of Enzymes Involved in Bacterial Lysine Biosynthesis

  摘要：

  [GRAPHICS]Vinylogous amides 5 and 6 have been synthesized from L-propargyl glycine and tested against diaminopimelate (DAP) enzymes involved in bacterial lysine biosynthesis, Both are reversible inhibitors of DAP D-dehydrogenase and DAP epimerase with IC50 values in the 500 muM range, Compound 5 shows competitive inhibition against the L-dihydrodipicolinate (DHDP) reductase with a K-i value of 32 muM, which is comparable to the planar dipicolinate 16 (K-i = 26 muM), the best known inhibitor of the enzyme.

  DOI：

  10.1021/ol000271e