1-(3-fluorophenyl)-1-methyl-3-(naphthalen-1-yl)guanidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(3-fluorophenyl)-1-methyl-3-(naphthalen-1-yl)guanidine
• 英文别名: 1-(3-Fluorophenyl)-1-methyl-2-naphthalen-1-ylguanidine
• 化学式: C₁₈H₁₆FN₃
• 分子量: 293.344
• InChiKey: YRXKTTDVPHLNHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-Fluorphenylcyanamid 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-(3-fluorophenyl)-1-methyl-3-(naphthalen-1-yl)guanidine
  参考文献：
  名称：

  Synthesis and in vitro evaluation of N,N′-diphenyl and N-naphthyl-N′-phenylguanidines as N-methyl-d-aspartate receptor ion-channel ligands

  摘要：

  A series of N,N'-diphenyl and N-naphthyl-N'-phenyl guanidine derivatives was synthesized as potential N-methyl-D-aspartate (NMDA) receptor positron emission tomography (PET) ligands. The affinity of the different compounds was determined using in vitro receptor binding assays, and their log P values were estimated using HPLC analysis. The effect of N'-3 and N-3,5 substitution on affinity and lipophilicity was examined. The K-i values ranged from 1.87 to 839 nM, while log P values between 1.22 and 2.88 were observed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00235-4

文献信息

• New N-aryl-N′-(3-(substituted)phenyl)-N′-methylguanidines as leads to potential PET radioligands for imaging the open NMDA receptor
  作者：Gregory R. Naumiec、Lisheng Cai、Victor W. Pike

  DOI：10.1016/j.bmcl.2014.11.066

  日期：2015.1

  vitro. Four ligands displayed affinities that are similar or superior to those of the promising SPECT radioligand ([123I]CNS1261). The 3′-dimethylamino (19; Ki 36.7 nM), 3′-trifluoromethyl (20; Ki 18.3 nM) and 3′-methylthio (2; Ki 39.8 nM) derivatives of N-1-naphthyl-N′-(phenyl)-N′-methylguanidine were identified as especially attractive leads for PET radioligand development.

  一个广阔的组ñ -芳基- ñ ' - （3-（取代的）苯基） - ñ '在为新的线索以预期PET配体的搜索制备用于所述的开口通道的成像-methylguanidines Ñ甲基d -体内天冬氨酸（NMDA）受体。所述Ñ芳基环和它们的取代基是变化的，而Ñ甲基组保持作为与正电子发射体，碳-11（潜在标记的位点吨1/2  = 20.4分钟）。在微摩尔浓度下，超过一半的制备化合物强烈抑制了[ 3H] TCP与其在体外NMDA受体中的结合位点有关。四个配体显示出与有希望的SPECT放射性配体（[ 123 I] CNS1261）相似或更高的亲和力。3'-二甲基氨基（19 ; ķ我36.7纳米），3'-三氟甲基（20 ; ķ我18.3 1nM）和3'-甲硫基（2 ; ķ我39.8纳米）的衍生物ñ -1-萘基Ñ ' -已确定（苯基）-N'-甲基胍是PET放射性配体发展的特别有吸引力的先导。
• Synthesis and in vitro evaluation of N,N′-diphenyl and N-naphthyl-N′-phenylguanidines as N-methyl-d-aspartate receptor ion-channel ligands
  作者：Filip Dumont、Abida Sultana、Rikki N Waterhouse

  DOI：10.1016/s0960-894x(02)00235-4

  日期：2002.6

  A series of N,N'-diphenyl and N-naphthyl-N'-phenyl guanidine derivatives was synthesized as potential N-methyl-D-aspartate (NMDA) receptor positron emission tomography (PET) ligands. The affinity of the different compounds was determined using in vitro receptor binding assays, and their log P values were estimated using HPLC analysis. The effect of N'-3 and N-3,5 substitution on affinity and lipophilicity was examined. The K-i values ranged from 1.87 to 839 nM, while log P values between 1.22 and 2.88 were observed. (C) 2002 Elsevier Science Ltd. All rights reserved.