tert-butyl [(1S,2S)-1-{[(R)-tert-butylsulfinyl]amino}-1-(4-fluorophenyl)-1-(6-fluoropyridin-3-yl)propan-2-yl]carbamate | 498538-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl [(1S,2S)-1-{[(R)-tert-butylsulfinyl]amino}-1-(4-fluorophenyl)-1-(6-fluoropyridin-3-yl)propan-2-yl]carbamate
• 英文别名: tert-butyl N-[(1S,2S)-1-[[(R)-tert-butylsulfinyl]amino]-1-(4-fluorophenyl)-1-(6-fluoropyridin-3-yl)propan-2-yl]carbamate
• CAS: 498538-85-5
• 化学式: C₂₃H₃₁F₂N₃O₃S
• 分子量: 467.58
• InChiKey: JXMKQINPLJIULF-CGRCSJLZSA-N

物化性质

• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  99.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl [(1S,2S)-1-{[(R)-tert-butylsulfinyl]amino}-1-(4-fluorophenyl)-1-(6-fluoropyridin-3-yl)propan-2-yl]carbamate 在 三氟乙酸 、 盐酸 、 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以100%的产率得到(1S,2S)-1-(4-fluorophenyl)-1-(6-fluoro-pyridin-3-yl)-1,2-propanediamine
  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-5-溴吡啶 、 tert-butyl [(1E,2S)-1-{[(R)-tert-butylsulfinyl]imino}-1-(4-fluorophenyl)propan-2-yl]carbamate 在 正丁基锂 、 三甲基铝 、 水 、 magnesium sulfate 、 sodium sulfate 作用下， 以 乙醚 、 正己烷 为溶剂， 以77%的产率得到tert-butyl [(1S,2S)-1-{[(R)-tert-butylsulfinyl]amino}-1-(4-fluorophenyl)-1-(6-fluoropyridin-3-yl)propan-2-yl]carbamate
  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