N-(3-hydroxyphenyl)-N-methylcyanamide | 508174-21-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3-hydroxyphenyl)-N-methylcyanamide
• 英文别名: N-methyl-3-hydroxyphenylcyanamide；(3-hydroxy-phenyl)-methyl-carbamonitrile；(3-Hydroxy-phenyl)-methyl-carbamonitril；Methyl-(3-oxy-phenyl)-cyanamid；3-Methylcyanamino-phenol；(3-Hydroxyphenyl)-methylcyanamide
• CAS: 508174-21-8
• 化学式: C₈H₈N₂O
• 分子量: 148.164
• InChiKey: VCGUPTJZNPZTPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-hydroxyphenyl)-N-methylcyanamide 在 potassium carbonate 、 potassium iodide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 生成 3-(2-chloro-5-(methylthio)phenyl)-1-(3-(3-fluoropropoxy)phenyl)-1-methylguanidine fumaric acid salt
  参考文献：
  名称：

  N-甲基-d-天门冬氨酸受体离子通道的高亲和力配体的合成，结构活性关系，放射性标记和临床前评估，可作为正电子发射断层扫描的潜在成像探针

  摘要：

  所述Ñ甲基d天冬氨酸受体（NMDAR）参与许多神经障碍和精神障碍，包括阿尔茨海默氏病和精神分裂症。目前，尚无法评估体内NMDAr的可用性。这项研究的目的是为NMDAr离子通道开发正电子发射断层扫描（PET）配体。合成了一系列二-和三-N-取代的二芳基胍。此外，评估了大鼠前脑膜部分中NMDAr离子通道的体外结合亲和力。化合物10，11和32与任一碳-11或氟-18放射性标记物。配体[ 11 C] 10和[ 18F] 32在B6C3小鼠中进行了离体评估。生物分布研究表明，与小脑相比，前脑区域对[ 11 C] 10和[ 18 F] 32的吸收更高。另外，对于[ 11 C] 10 54％和[ 18 F] 32，在60分钟时大脑中70％的活动归因于完整的示踪剂。用MK-801（0.6 mg·kg -1，ip）进行的预处理稍微降低了NMDAr特定区域对[ 18 F] 32的吸收，但没有降低[ 11 C]

  DOI：

  10.1016/j.bmc.2014.12.029
• 作为产物：
  描述：

  3-羟基苯基硫脲 在 氢氧化钾 、 alkaline solution 、 lead(II) oxide 作用下， 生成 N-(3-hydroxyphenyl)-N-methylcyanamide
  参考文献：
  名称：

  DE484906

  摘要：

  公开号：

文献信息

• [EN] N,N-SUBSTITUTED GUANIDINE COMPOUND<br/>[FR] COMPOSÉ DE GUANIDINE N,N-SUBSTITUÉE
  申请人：VERENIGING VOOR CHRISTELIJK HOGER ONDERWIJS WETENSCHAPPELIJK ONDERZOEK EN PATIENTENZORG

  公开号：WO2012165956A1

  公开（公告）日：2012-12-06

  The invention is directed to a N, N-substituted guanidine compound or a salt or solvate thereof according to formula (1), R1RNC(NH)NR2R3, wherein R1 is methyl and R2 is hydrogen. R3 is a organic group comprising a halogen and thiomethyl substituted phenyl group. R is an organic group comprising a substituted aryl group Z wherein the substituent group is -Y-R4, wherein Y is a heteroatom chosen from the group consisting of O, S and N and R4 is a fluorinated organic group.

  该发明涉及一种N，N-取代胍啶化合物或其盐或溶剂化合物，其化学式为（1），R1RNC（NH）NR2R3，其中R1为甲基，R2为氢。R3是一个包含卤素和硫甲基取代苯基的有机基团。R是一个包含取代芳基Z的有机基团，其中取代基团为-Y-R4，其中Y是从O、S和N组成的杂原子，R4是氟化有机基团。
• Synthesis of [11C]N-(2-chloro-5-thiomethylphenyl)-N?-(3-methoxyphenyl)-N?-methylguanidine ([11C]GMOM): a candidate PET tracer for imaging the PCP site of the NMDA ion channel
  作者：Rikki N. Waterhouse、Filip Dumont、Abida Sultana、Norman Simpson、Marc Laruelle

  DOI：10.1002/jlcr.622

  日期：2002.10.15

  therapeutic drugs. Since the NMDA/PCP receptor lies within the channel, it is a unique target and is theoretically accessible only when the channel is in the active and "open" state, but not when it is in the inactive or "closed" state. The physical location of the NMDA/PCP receptor not only makes it an important imaging target but also complicates the development of suitable PET and SPECT radiotracers for

  N-甲基-D-天冬氨酸 (NMDA) 离子通道在神经保护、神经变性、长时程增强、记忆和认知中发挥作用。它涉及多种神经和神经精神疾病的病理生理学，包括帕金森病、亨廷顿舞蹈病、精神分裂症、酒精中毒和中风。开发用于研究 NMDA 受体的有效放射性示踪剂对于我们了解它们的功能以及它们由内源性物质或治疗药物进行的调节至关重要。由于 NMDA/PCP 受体位于通道内，因此它是一个独特的目标，理论上只有当通道处于活动和“开放”状态时才可访问，而在非活动或“关闭”状态时则不能访问。NMDA/PCP 受体的物理位置不仅使其成为一个重要的成像目标，而且使该部位合适的 PET 和 SPECT 放射性示踪剂的开发变得复杂。深入了解与 NMDA 离子通道相关的生化、药理、生理和行为过程对于开发改进的显像剂至关重要。本综述概述了为 NMDA 离子通道的 PCP 位点开发放射性标记试剂的进展。此外，还讨论了用于 NMDA
• Synthesis, radiolabeling and preclinical evaluation of a [ 11 C]GMOM derivative as PET radiotracer for the ion channel of the N-methyl-D-aspartate receptor
  作者：Pieter J. Klein、Robert C. Schuit、Athanasios Metaxas、Johannes A.M. Christiaans、Esther Kooijman、Adriaan A. Lammertsma、Bart N.M. van Berckel、Albert D. Windhorst

  DOI：10.1016/j.nucmedbio.2017.05.003

  日期：2017.8

  Introduction: Presently available PET ligands for the NMDAr ion channel generally suffer from fast metabolism. The purpose of this study was to develop a metabolically more stable ligand for the NMDAr ion channel, taking [C-11]GMOM ([C-11]1) as the lead compound.Methods: [C-11]1, its fluoralkyl analogue [F-18]PK209 ([F-18]2) and the newly synthesized fluorovinyloxy analogue [C-11]7b were evaluated ex vivo in male Wistar rats for metabolic stability. In addition, [C-11]7b was subjected to a biodistribution study and its affinity (K-i) and lipophilicity (logD(7.4)) values were determined.Results: The addition of a vinyl chain in the fluoromethoxy moiety did not negatively alter the affinity of [C-11]7b for the NMDAr, while lipophilicity was increased. Biodistribution studies showed higher uptake of [C-11]7b in forebrain regions compared with cerebellum. Pre-treatment with MK-801 decreased the overall brain uptake significantly, but not in a region-specific manner. 45 min after injection 78, 90 and 87% of activity in the brain was due to parent compound for and [C-11]1, [F-18]2 and [C-11]7b, respectively. In plasma, 26-31% of activity was due to parent compound.Conclusion: Complete substitution of the alpha-carbon increased lipophilicity to more favorable values. Substitution of one or more hydrogens of the alpha-carbon atom in the methoxy moiety improved metabolic stability. In plasma, more parent compound was found for [F-18]2 and [C-11]7b then for [C-11]1, although differences were not significant. At 45 min, significantly more parent [F-18]2 and [C-11]7b was measured in the brain compared with [C-11]1. (C) 2017 The Authors. Published by Elsevier Inc.
• N,N-SUBSTITUTED GUANIDINE COMPOUND
  申请人：Klein Pieter Jacob

  公开号：US20140154182A1

  公开（公告）日：2014-06-05

  The invention is directed to a N,N-substituted guanidine compound or a salt or solvate thereof according to formula (1), R 1 RNC(NH)NR 2 R 3 , wherein R 1 is methyl and R 2 is hydrogen. R 3 is a organic group comprising a halogen and thiomethyl substituted phenyl group. R is an organic group comprising a substituted aryl group Z wherein the substituent group is —Y—R 4 , wherein Y is a heteroatom chosen from the group consisting of O, S and N and R 4 is a fluorinated organic group.