N-<3-(4-fluorophenoxy)propyl>-N-methyl-2-propynylamine | 135062-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-<3-(4-fluorophenoxy)propyl>-N-methyl-2-propynylamine
• 英文别名: N-[3-(4-fluorophenoxy)propyl]-N-methyl-2-propagylamine；3-(4-fluorophenoxy)-N-methyl-N-prop-2-ynylpropan-1-amine
• CAS: 135062-16-7
• 化学式: C₁₃H₁₆FNO
• 分子量: 221.275
• InChiKey: KAKMAYRTXAATGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氟苯酚 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 51.0h， 生成 N-<3-(4-fluorophenoxy)propyl>-N-methyl-2-propynylamine
  参考文献：
  名称：

  Synthesis of fluorine and iodine analogues of clorgyline and selective inhibition of monoamine oxidase A.

  摘要：

  合成了一系列氯吉林的氟和碘类似物，并评估了其对单胺氧化酶 A (MAO-A) 的抑制效力和选择性。其中，N-[3(2,4-二氯-6-碘苯氧基)丙基]-N-甲基-2-丙炔胺(3d)、N-[3-(4-氯-2-氟苯氧基)丙基]-N发现-甲基-2-丙炔胺 (3f) 和 N-[3-(2-氯-4-氟苯氧基)丙基]-N-甲基-2-丙炔胺 (3g) 对 MAO-A 具有高抑制效力和选择性与氯吉林本身的效果相当。因此，它们被认为是作为放射性氟化和放射性碘化配体进行高级开发，可能有助于利用正电子发射断层扫描和单光子发射计算机断层扫描对活体大脑进行功能性 MAO-A 研究。

  DOI：

  10.1248/cpb.39.1038

文献信息

• ¹H NMR Probe for in Situ Monitoring of Dopamine Metabolism and Its Application to Inhibitor Screening
  作者：Ryosuke Ueki、Koya Yamaguchi、Hiroshi Nonaka、Shinsuke Sando

  DOI：10.1021/ja305051u

  日期：2012.8.1

  Dopamine (DA) is a monoamine neurotransmitter that plays important roles in the brain, and whose levels in the brain are associated with several neurological and psychiatric disorders. Therefore, DA metabolism inhibitors have been used as therapeutic agents. Here, we report a H-1 NMR probe for the in situ analysis of DA metabolism, and its application to DA inhibitor screening. We designed doubly C-13-labeled DA (C-13(2)-DA) as the probe. The combination of the C-13(2)-DA and H-1-C-13-C-13'} NMR technique allowed the selective and thus in situ monitoring of DA metabolism. Using C-13(2)-DA, we successfully measured the efficacies of different inhibitors in a tissue sample, allowing us to improve the in situ inhibitory efficacy of the known DA metabolism inhibitor, clorgyline.
• Synthesis of fluorine and iodine analogues of clorgyline and selective inhibition of monoamine oxidase A.
  作者：Yoshiro OHMOMO、Masahiko HIRATA、Katsuhiko MURAKAMI、Yasuhiro MAGATA、Chiaki TANAKA、Akira YOKOYAMA

  DOI：10.1248/cpb.39.1038

  日期：——

  A series of fluorine and iodine analogues of clorgyline was synthesized and evaluated for inhibitory potency and selectivity toward monoamine oxidase A (MAO-A). Among them, N-[3(2, 4-dichloro-6-iodophenoxy)propyl]-N-methyl-2-propynylamine (3d), N-[3-(4-chloro-2-fluorophenoxy)propyl]-N-methyl-2-propynylamine (3f) and N-[3-(2-chloro-4-fluorophenoxy)propyl]-N-methyl-2-propynylamine (3g) were found to have high inhibitory potency and selectivity toward MAO-A comparable to those of clorgyline itself. Thus, they were considered for advanced development as radiofluorinated and radioiodinated ligands that may be useful for functional MAO-A studies in the living brain with positron emission tomography and single photon emission computer tomography.

  合成了一系列氯吉林的氟和碘类似物，并评估了其对单胺氧化酶 A (MAO-A) 的抑制效力和选择性。其中，N-[3(2,4-二氯-6-碘苯氧基)丙基]-N-甲基-2-丙炔胺(3d)、N-[3-(4-氯-2-氟苯氧基)丙基]-N发现-甲基-2-丙炔胺 (3f) 和 N-[3-(2-氯-4-氟苯氧基)丙基]-N-甲基-2-丙炔胺 (3g) 对 MAO-A 具有高抑制效力和选择性与氯吉林本身的效果相当。因此，它们被认为是作为放射性氟化和放射性碘化配体进行高级开发，可能有助于利用正电子发射断层扫描和单光子发射计算机断层扫描对活体大脑进行功能性 MAO-A 研究。