methyl 2-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylate | 1189757-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 2-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylate
• 英文别名: Methyl 2-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylate；methyl 2-fluoro-6-oxo-1H-pyridine-3-carboxylate
• CAS: 1189757-67-2
• 化学式: C₇H₆FNO₃
• 分子量: 171.128
• InChiKey: PRZPAOBQWMPIET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylate 、 溴甲苯 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 methyl 6-(benzyloxy)-2-fluoropyridine-3-carboxylate
  参考文献：
  名称：

  Discovery of pyridone-containing imidazolines as potent and selective inhibitors of neuropeptide Y Y5 receptor

  摘要：

  A series of 2-pyridone-containing imidazoline derivatives was synthesized and evaluated as neuropeptide Y Y5 receptor antagonists. Optimization of the 2-pyridone structure on the 2-position of the imidazoline ring led to identification of 1-(difluoromethyl)-5-[(4S,5S)-4-(4-fluorophenyl)-4-(6-fluoropyridin- 3-yl)-5-methyl-4,5-dihydro-1H-imidazol-2-yl] pyridin-2(1H)-one (7m). Compound 7m displayed statistically significant inhibition of food intake in an agonist-induced food intake model in SD rats and no adverse cardiovascular effects in anesthetized dogs. In addition, markedly higher brain penetrability and a lower plasma Occ90 value were observed in P-gp-deficient mdr1a (-/-) mice compared to mdr1a (+/+) mice after oral administration of 7m. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.069
• 作为产物：
  描述：

  2-氟-6-甲氧基烟酸甲酯 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 17.0h， 以69%的产率得到methyl 2-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Discovery of pyridone-containing imidazolines as potent and selective inhibitors of neuropeptide Y Y5 receptor

  摘要：

  A series of 2-pyridone-containing imidazoline derivatives was synthesized and evaluated as neuropeptide Y Y5 receptor antagonists. Optimization of the 2-pyridone structure on the 2-position of the imidazoline ring led to identification of 1-(difluoromethyl)-5-[(4S,5S)-4-(4-fluorophenyl)-4-(6-fluoropyridin- 3-yl)-5-methyl-4,5-dihydro-1H-imidazol-2-yl] pyridin-2(1H)-one (7m). Compound 7m displayed statistically significant inhibition of food intake in an agonist-induced food intake model in SD rats and no adverse cardiovascular effects in anesthetized dogs. In addition, markedly higher brain penetrability and a lower plasma Occ90 value were observed in P-gp-deficient mdr1a (-/-) mice compared to mdr1a (+/+) mice after oral administration of 7m. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.069

文献信息

• Discovery of pyridone-containing imidazolines as potent and selective inhibitors of neuropeptide Y Y5 receptor
  作者：Makoto Ando、Nagaaki Sato、Tsuyoshi Nagase、Keita Nagai、Shiho Ishikawa、Hirobumi Takahashi、Norikazu Ohtake、Junko Ito、Mioko Hirayama、Yuko Mitobe、Hisashi Iwaasa、Akira Gomori、Hiroko Matsushita、Kiyoshi Tadano、Naoko Fujino、Sachiko Tanaka、Tomoyuki Ohe、Akane Ishihara、Akio Kanatani、Takehiro Fukami

  DOI：10.1016/j.bmc.2009.05.069

  日期：2009.8

  A series of 2-pyridone-containing imidazoline derivatives was synthesized and evaluated as neuropeptide Y Y5 receptor antagonists. Optimization of the 2-pyridone structure on the 2-position of the imidazoline ring led to identification of 1-(difluoromethyl)-5-[(4S,5S)-4-(4-fluorophenyl)-4-(6-fluoropyridin- 3-yl)-5-methyl-4,5-dihydro-1H-imidazol-2-yl] pyridin-2(1H)-one (7m). Compound 7m displayed statistically significant inhibition of food intake in an agonist-induced food intake model in SD rats and no adverse cardiovascular effects in anesthetized dogs. In addition, markedly higher brain penetrability and a lower plasma Occ90 value were observed in P-gp-deficient mdr1a (-/-) mice compared to mdr1a (+/+) mice after oral administration of 7m. (C) 2009 Elsevier Ltd. All rights reserved.