2-(1-金刚烷基)-1-(4-碘苯基)胍 | 133985-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(1-金刚烷基)-1-(4-碘苯基)胍
• 英文名称: N-p-iodophenyl-N'-adamantyl guanidine
• 英文别名: 1-(p-iodophenyl)-3-(1-adamantyl)guanidine；(1-adamantan-1-yl)-3-(4-iodophenyl)guanidine；IPAG；[125I]-PIPAG；N-(adamant-1-yl)-N'-(p-iodophenyl)guanidine；PIPAG；1-(4-Iodophenyl)-3-(1-adamantyl)guanidine；2-(1-adamantyl)-1-(4-iodophenyl)guanidine
• CAS: 133985-85-0
• 化学式: C₁₇H₂₂IN₃
• 分子量: 395.286
• InChiKey: BNRDJYCVXAIEIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-adamantylcyanamide 、 4-碘苯胺盐酸盐 反应 1.75h， 以55.5%的产率得到2-(1-金刚烷基)-1-(4-碘苯基)胍
  参考文献：
  名称：

  Radiosynthesis, cerebral distribution, and binding of [125I]-1-(p-iodophenyl)-3-(1-adamantyl)guanidine, a ligand for .sigma. binding sites

  摘要：

  An analog of 1,3-di-o-tolylguanidine (DTG), [I-125]-labeled 1-(p-iodophenyl)-3-(1-adamantyl)-guanidine (PIPAG), was synthesized as a potential ligand for cerebral sigma binding sites. Data from in vitro binding experiments and in vivo experiments on brain distribution suggested that PIPAG binds to sigma binding sites with high affinity (K(d) in low nanomolar range) as determined by Scatchard analysis and relative potencies of sigma-specific drugs. Haloperidol had the highest potency to inhibit [I-125]PIPAG binding. It was followed by DTG, BMY 14802, and (+)-N-allylnormetazocine. Compounds with high affinities for dopamine receptors (but low affinity for sigma binding sites), for opioid receptors, for nicotinic acetylcholine receptors, and for phencyclidine receptors were ineffective inhibitors of [I-125]PIPAG binding.

  DOI：

  10.1021/jm00103a005

文献信息

• A traceless linker approach to the solid phase synthesis of substituted guanidines utilizing a novel acyl isothiocyanate resin
  作者：Lawrence J. Wilson、Sean R. Klopfenstein、Min Li

  DOI：10.1016/s0040-4039(99)00663-2

  日期：1999.5

  Solid phase synthesis of a series of substituted guanidines based on a novel acyl isothiocyanate resin is presented. This method provides both mono and disubstituted guanidines with a variety of sterically demanding and/or electron withdrawing substituents in good purities and yields.

  提出了基于新型酰基异硫氰酸酯树脂的一系列取代胍的固相合成。该方法以良好的纯度和收率提供具有各种空间需求和/或吸电子取代基的单取代的和二取代的胍。
• Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
  申请人：CAMBRIDGE NEUROSCIENCE RESEARCH, INC.

  公开号：EP0940139A2

  公开（公告）日：1999-09-08

  Modulators of neurotransmitter release including substituted guanidines, N''-aminoguanidines, and N,N',N'',N'''-tetra-substituted hydrazinedicarboximidamides, and pharmaceutical compositions thereof are disclosed. Also disclosed are methods involving the use of such neurotransmitter release modulators for the treatment or prevention of pathophysiologic conditions characterized by the release of excessive or inappropriate levels of neurotransmitters. Also disclosed are screening assays for compounds which selectively inhibit glutamate release. Also disclosed are methods of blocking voltage sensitive sodium and calcium channels in mammalian nerve cells.

  本发明公开了包括取代胍类、N''-氨基胍类和 N,N',N'',N'''-四取代肼二甲酰亚胺在内的神经递质释放调节剂及其药物组合物。还公开了涉及使用此类神经递质释放调节剂治疗或预防以神经递质释放过量或不适当水平为特征的病理生理状况的方法。还公开了选择性抑制谷氨酸释放的化合物的筛选试验。还公开了阻断哺乳动物神经细胞中电压敏感钠和钙通道的方法。
• Radiosynthesis of .sigma. receptor ligands for positron emission tomography: carbon-11 and fluorine-18 labeled guanidines
  作者：Alan A. Wilson、Robert F. Dannals、Hayden T. Ravert、Mark S. Sonders、Eckard Weber、Henry N. Wagner

  DOI：10.1021/jm00110a017

  日期：1991.6

  A series of analogues of the potent and selective sigma-receptor ligand 1,3-ditolylguanidine (DTG) were synthesized and demonstrated to have high affinity for the sigma-receptor as measured by in vitro [H-3]DTG displacement studies using guinea pig brain tissue. Three of these 1-aryl-3-(1-adamantyl)guanidines were radiolabeled - two with carbon-11 and one with fluorine-18. Radiochemical yields and specific activities were sufficient for these radiotracers to be used in positron emission tomography imaging of the haloperidol-sensitive sigma-receptor.
• SUBSTITUTED GUANIDINES HAVING HIGH BINDING TO THE SIGMA RECEPTOR AND THE USE THEREOF
  申请人：STATE OF OREGON, acting by and through THE OREGON STATE BOARD OF HIGHER EDUCATION, acting for and on behalf of

  公开号：EP0532642A1

  公开（公告）日：1993-03-24
• EP0532642A4
  申请人：——

  公开号：EP0532642A4

  公开（公告）日：1994-04-27