CNS 1261

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: CNS 1261
• 英文别名: 1-(3-iodophenyl)-1-methyl-3-(naphthalen-1-yl)guanidine；1-methyl-3-(naphthalen-1-yl)-1-(3-iodo)phenylguanidine；N-(1-naphthyl)-N'-(3-iodophenyl)-N'-methylguanidine；CNS1261；1-(3-Iodophenyl)-1-methyl-3-(1-naphthyl)guanidine；1-(3-iodophenyl)-1-methyl-2-naphthalen-1-ylguanidine
• 化学式: C₁₈H₁₆IN₃
• 分子量: 401.25
• InChiKey: YEMFBSCVGTUXHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  1

反应信息

• 作为产物：
  描述：

  N-methyl-N-(3-nitrophenyl)cyanamide 在 盐酸 、 tin(II) chloride dihdyrate 、 对甲苯磺酸 、 sodium iodide 作用下， 以 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 35.0h， 生成 CNS 1261
  参考文献：
  名称：

  使用一锅法从芳基胺中进行生物活性剂的后期碘化†

  摘要：

  已经开发了一种简单有效的一锅串联程序，该程序通过稳定的重氮盐从容易获得的芳基胺生成芳基碘化物。操作简单的程序和温和的条件允许对各种带有各种官能团和取代方式的芳基化合物进行后期碘化。还开发了一种新颖的合成策略，包括制备硝基芳基化合物，然后还原化学选择性的二氯化锡（II）以及使用一锅重氮化-碘化转化反应。通过制备许多具有医学重要性的化合物，包括CNS1261（一种N-甲基-D的SPECT显像剂），证明了该方法的普遍适用性。-天冬氨酸（NMDA）受体和IBOX，一种用于检测大脑淀粉样斑块的化合物。

  DOI：

  10.1039/c7ra11860k

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。
• A one-pot radioiodination of aryl amines via stable diazonium salts: preparation of ¹²⁵I-imaging agents
  作者：Nikki L. Sloan、Sajinder K. Luthra、Graeme McRobbie、Sally L. Pimlott、Andrew Sutherland

  DOI：10.1039/c7cc06211g

  日期：——

  An operationally simple, one-pot, two-step tandem procedure that allows the incorporation of radioactive iodine into aryl amines via stable diazonium salts is described. The mild conditions are tolerant of various functional groups and substitution patterns, allowing late-stage, rapid access to a wide range of 125I-labelled aryl compounds and SPECT radiotracers.

  描述了一种操作简单，一锅，两步的串联程序，该程序允许将放射性碘通过稳定的重氮盐掺入芳基胺中。温和的条件可以耐受各种官能团和取代模式，从而可以后期快速地获得各种125 I标记的芳基化合物和SPECT放射性示踪剂。
• <i>N</i>′-3-(Trifluoromethyl)phenyl Derivatives of <i>N</i>-Aryl-<i>N</i>′-methylguanidines as Prospective PET Radioligands for the Open Channel of the <i>N</i>-Methyl-<scp>d</scp>-aspartate (NMDA) Receptor: Synthesis and Structure–Affinity Relationships
  作者：Gregory R. Naumiec、Kimberley J. Jenko、Sami S. Zoghbi、Robert B. Innis、Lisheng Cai、Victor W. Pike

  DOI：10.1021/acs.jmedchem.5b01510

  日期：2015.12.24

  N-Methyl-D-aspartate (NMDA) receptor dysfunction has been linked to several neuropsychiatric disorders, including Alzheimer's disease, epilepsy, drug addiction, and schizophrenia. A radioligand that could be used with PET to image and quantify human brain. NMDA receptors in the activated "open channel" state would be useful for research on such disorders and for the development of novel therapies,: To date, no radioligands have Shown well-validated efficacy for imaging NMDA receptors in human subjects. In order to discover improved radioligands for PET imaging, we explored structure affinity relationships in N'-3-(trifluoromethyl)phenyl derivatives of N-aryl-N'-methylguanidines, seeking high affinity and moderate lipophilicity, plus necessary amenability for labeling with a positron-emitter, either carbon-11 or fluorine-18. Among a diverse set of 80 prepared N'-3-(trifluoromethyl)phenyl derivatives, four of these compounds (13, 19, 20, and 36) displayed desirable low nanomolar affinity for inhibition of [H-3](+)-MK801 at the PCP binding site and are of interest for candidate PET radioligand development.
• 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.