methyl 6-dimethylamino-2-fluoropyridine-3-carboxylate | 210697-20-4

• 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 6-dimethylamino-2-fluoropyridine-3-carboxylate
• 英文别名: Methyl 6-(dimethylamino)-2-fluoronicotinate；methyl 6-(dimethylamino)-2-fluoropyridine-3-carboxylate
• CAS: 210697-20-4
• 化学式: C₉H₁₁FN₂O₂
• 分子量: 198.197
• InChiKey: DDRVSQDSMWRGAB-UHFFFAOYSA-N

物化性质

• 沸点：
  310.9±42.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-dimethylamino-2-fluoropyridine-3-carboxylate 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-bromo-6-dimethylamino-2-methoxypyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)nicotinamides and their affinities for 5-HT3 and dopamine D2 receptors

  摘要：

  A series of N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl) derivatives were prepared and evaluated for their binding to 5-HT3 and dopamine D-2 receptors. Among them, the 5-bromo-2-methoxy-6-methylaminonicotinamide 16 and its (R)-isomer were found to have potent affinities for both receptors. The affinities of(R)-16 for 5-HT3 and dopamine D-2 receptors are approximately 3-fold higher than those of the corresponding benzamide (R)-1 (IC50:1.1 and 12 nM vs. 2.9 and 35 nM, respectively). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00258-3
• 作为产物：
  描述：

  2,6-二氟烟酸 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 6-dimethylamino-2-fluoropyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis of N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)nicotinamides and their affinities for 5-HT3 and dopamine D2 receptors

  摘要：

  A series of N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl) derivatives were prepared and evaluated for their binding to 5-HT3 and dopamine D-2 receptors. Among them, the 5-bromo-2-methoxy-6-methylaminonicotinamide 16 and its (R)-isomer were found to have potent affinities for both receptors. The affinities of(R)-16 for 5-HT3 and dopamine D-2 receptors are approximately 3-fold higher than those of the corresponding benzamide (R)-1 (IC50:1.1 and 12 nM vs. 2.9 and 35 nM, respectively). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00258-3

文献信息

• Synthesis and Structure−Affinity Relationships of Novel <i>N</i>-(1-Ethyl-4-methylhexahydro-1,4-diazepin-6-yl)pyridine-3-carboxamides with Potent Serotonin 5-HT₃ and Dopamine D₂ Receptor Antagonistic Activity
  作者：Yoshimi Hirokawa、Iwao Fujiwara、Kenji Suzuki、Hiroshi Harada、Takashi Yoshikawa、Naoyuki Yoshida、Shiro Kato

  DOI：10.1021/jm020270n

  日期：2003.2.1

  dopamine D(2) receptor while keeping a potent serotonin 5-HT(3) receptor binding affinity. As a result of structure-affinity relationships, the 5-bromo-2-methoxy-6-methylaminopyridine-3-carboxamide 53 was selected as the most promising product showing a high binding affinity for both receptors. Compound 53 affinity for the dopamine D(2) and serotonin 5-HT(3) receptors was much more potent than that of

  制备了由相应的苯甲酰胺5衍生的N-（1-乙基-4-甲基六氢-1,4-二氮杂-6-6-基）吡啶-3-甲酰胺的结构原始系列，并评估了其对多巴胺D（ 2）和分别使用大鼠纹状体和大鼠皮质膜的血清素5-HT（3）受体。许多合成的吡啶-3-羧酰胺对5-羟色胺5-HT（3）受体具有纳摩尔结合亲和力，对多巴胺D（2）受体具有中等至高结合亲和力。在吡啶环的5-位和6-位上分别引入更具亲脂性的溴原子和甲基氨基，增强了对多巴胺D（2）受体的亲和力，同时保持了强大的5-羟色胺5-HT（3）受体结合亲和力。由于结构相似性关系，选择5-溴-2-甲氧基-6-甲基氨基吡啶-3-羧酰胺53作为最有前途的产品，该产品对两种受体都具有高结合亲和力。化合物53对多巴胺D（2）和5-羟色胺5-HT（3）受体的亲和力比甲氧氯普胺（多巴胺D（2）受体； 23.3 nM对444 nM，5-羟色胺5-HT（3）受体的亲和力强得多。 0.97