1-(2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane | 774160-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane
• 英文别名: 2-(2,3,6,7-Tetrahydro-benzo[1,2-b;4,5-b'']difuran-4-yl)-ethylamine；2-(2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-4-yl)ethanamine
• CAS: 774160-87-1
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: TUZLDMANNCPSHX-UHFFFAOYSA-N

物化性质

• 沸点：
  363.8±31.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane 在 溴 、 溶剂黄146 作用下， 反应 2.25h， 以73%的产率得到1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane
  参考文献：
  名称：

  Dihydrobenzofuran Analogues of Hallucinogens. 3. Models of 4-Substituted (2,5-Dimethoxyphenyl)alkylamine Derivatives with Rigidified Methoxy Groups

  摘要：

  Tetrahydrobenzodifuran functionalities were employed as conformationally restricted bioisosteres of the aromatic methoxy groups in prototypical hallucinogenic phenylalkylamines 1 and 2. Thus, a series of 8-substituted 1-(2,3,6,7-tetrahydrobenzo[ 1,2-b:4,5-b']difuran-4-yl)-2-aminoalkanes (7a-e) were prepared and evaluated for activity in the two-lever drug discrimination paradigm in rats trained to discriminate saline from LSD tartrate (0.08 mg/kg) and for the ability to displace [H-3]ketanserin from rat cortical homogenate 5-HT2A receptors and [(3)H3-8-OH-DPAT from rat hippocampal homogenate 5-HT1A receptors. In addition, 1-(8-(bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5- (7b), which was found to be extremely potent in the rat in vivo assays, was evaluated for its ability to compete with [I-125][DOI and [H-3]ketanserin binding to cells expressing cloned human 5-HT2A, 5-H-2B, and 5-HT2C receptors. All of the dihydrofuranyl compounds having a hydrophobic substituent para to the alkylamine side chain had activities in both the in vitro and in vivo assays that equaled or surpassed the activity of the analogous conformationally flexible parent compounds. For example, 7b substituted for LSD in the drug discrimination assay with an ED(50) Of 61 nmol/kg and had K-i values in the nanomolar to subnanomolar range for the displacement of radioligand from rat and human 5-HT2 receptors, making it one of the most potent hallucinogen-like phenylalkylamine derivatives reported to date. The results suggest that the dihydrofuran rings in these pew analogues effectively model the active binding conformations of the methoxy groups of the parent compounds 1 and 2. In addition, the results provide information about the topography and relative orientation of residues involved in agonist binding in the serotonin 5-HT2 receptors.

  DOI：

  10.1021/jm960199j
• 作为产物：
  描述：

  2,3,6,7-四氢呋喃并[2,3-f][1]苯并呋喃 在 lithium aluminium tetrahydride 、 ammonium acetate 、 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 1-(2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane
  参考文献：
  名称：

  Dihydrobenzofuran Analogues of Hallucinogens. 3. Models of 4-Substituted (2,5-Dimethoxyphenyl)alkylamine Derivatives with Rigidified Methoxy Groups

  摘要：

  Tetrahydrobenzodifuran functionalities were employed as conformationally restricted bioisosteres of the aromatic methoxy groups in prototypical hallucinogenic phenylalkylamines 1 and 2. Thus, a series of 8-substituted 1-(2,3,6,7-tetrahydrobenzo[ 1,2-b:4,5-b']difuran-4-yl)-2-aminoalkanes (7a-e) were prepared and evaluated for activity in the two-lever drug discrimination paradigm in rats trained to discriminate saline from LSD tartrate (0.08 mg/kg) and for the ability to displace [H-3]ketanserin from rat cortical homogenate 5-HT2A receptors and [(3)H3-8-OH-DPAT from rat hippocampal homogenate 5-HT1A receptors. In addition, 1-(8-(bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5- (7b), which was found to be extremely potent in the rat in vivo assays, was evaluated for its ability to compete with [I-125][DOI and [H-3]ketanserin binding to cells expressing cloned human 5-HT2A, 5-H-2B, and 5-HT2C receptors. All of the dihydrofuranyl compounds having a hydrophobic substituent para to the alkylamine side chain had activities in both the in vitro and in vivo assays that equaled or surpassed the activity of the analogous conformationally flexible parent compounds. For example, 7b substituted for LSD in the drug discrimination assay with an ED(50) Of 61 nmol/kg and had K-i values in the nanomolar to subnanomolar range for the displacement of radioligand from rat and human 5-HT2 receptors, making it one of the most potent hallucinogen-like phenylalkylamine derivatives reported to date. The results suggest that the dihydrofuran rings in these pew analogues effectively model the active binding conformations of the methoxy groups of the parent compounds 1 and 2. In addition, the results provide information about the topography and relative orientation of residues involved in agonist binding in the serotonin 5-HT2 receptors.

  DOI：

  10.1021/jm960199j

文献信息

• 2C-B-Fly-NBOMe Metabolites in Rat Urine, Human Liver Microsomes and C. elegans: Confirmation with Synthesized Analytical Standards
  作者：Jitka Nykodemová、Anna Šuláková、Petr Palivec、Hedvika Češková、Silvie Rimpelová、Klára Šíchová、Tereza Leonhardt、Bronislav Jurásek、Kateřina Hájková、Tomáš Páleníček、Martin Kuchař

  DOI：10.3390/metabo11110775

  日期：——

  were observed for the three used media. The highest number of metabolites and at highest concentration were found in human liver microsomes. In vivo metabolites detected from rat urine included two poly-hydroxylated metabolites found only in this media. Mycelium matrix contained several dehydrogenated, N-oxygenated, and dibrominated metabolites.

  从化合物Ñ -benzylphenethylamine（NBPEA）类的新颖的精神活性物质在神经生物学和临床研究正在越来越多地利用，作为诊断工具或用于娱乐目的。因此，要了解这些物质的药理学、安全性或潜在毒性，阐明它们的代谢命运是最重要的。一些关于 NBPEA 代谢的研究已经出现，但关于具有四氢苯并二呋喃（“苍蝇”）部分的物质的信息很少。在这里，我们研究了 2-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl) -N- (2-methoxybenzyl ) 的代谢)ethan-1-amine (2C-B-Fly-NBOMe) 在三种不同的系统中：分离的人肝微粒体、Cunninghamella elegans菌丝体，并在大鼠体内。2C-B-Fly-NBOMe 的 I 和 II 相代谢物首先在非靶向筛选中检测到，并通过液相色谱-串联质谱
• [EN] PHENALKYLAMINES AND METHODS OF TREATING MOOD DISORDERS<br/>[FR] PHÉNALKYLAMINES ET PROCÉDÉS DE TRAITEMENT DE TROUBLES DE L'HUMEUR
  申请人：GILGAMESH PHARMACEUTICALS INC

  公开号：WO2022006186A1

  公开（公告）日：2022-01-06

  Phenalkylamines and methods of treating mood disorders with phenalkylamines. Also provided are pharmaceutical compositions that include phenalkylamines.

  Phenalkylamines和使用Phenalkylamines治疗情绪障碍的方法。还提供了包含Phenalkylamines的制药组合物。
• Dihydrobenzofuran Analogues of Hallucinogens. 3. Models of 4-Substituted (2,5-Dimethoxyphenyl)alkylamine Derivatives with Rigidified Methoxy Groups
  作者：Aaron P. Monte、Danuta Marona-Lewicka、Matthew A. Parker、David B. Wainscott、David L. Nelson、David E. Nichols

  DOI：10.1021/jm960199j

  日期：1996.1.1

  Tetrahydrobenzodifuran functionalities were employed as conformationally restricted bioisosteres of the aromatic methoxy groups in prototypical hallucinogenic phenylalkylamines 1 and 2. Thus, a series of 8-substituted 1-(2,3,6,7-tetrahydrobenzo[ 1,2-b:4,5-b']difuran-4-yl)-2-aminoalkanes (7a-e) were prepared and evaluated for activity in the two-lever drug discrimination paradigm in rats trained to discriminate saline from LSD tartrate (0.08 mg/kg) and for the ability to displace [H-3]ketanserin from rat cortical homogenate 5-HT2A receptors and [(3)H3-8-OH-DPAT from rat hippocampal homogenate 5-HT1A receptors. In addition, 1-(8-(bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5- (7b), which was found to be extremely potent in the rat in vivo assays, was evaluated for its ability to compete with [I-125][DOI and [H-3]ketanserin binding to cells expressing cloned human 5-HT2A, 5-H-2B, and 5-HT2C receptors. All of the dihydrofuranyl compounds having a hydrophobic substituent para to the alkylamine side chain had activities in both the in vitro and in vivo assays that equaled or surpassed the activity of the analogous conformationally flexible parent compounds. For example, 7b substituted for LSD in the drug discrimination assay with an ED(50) Of 61 nmol/kg and had K-i values in the nanomolar to subnanomolar range for the displacement of radioligand from rat and human 5-HT2 receptors, making it one of the most potent hallucinogen-like phenylalkylamine derivatives reported to date. The results suggest that the dihydrofuran rings in these pew analogues effectively model the active binding conformations of the methoxy groups of the parent compounds 1 and 2. In addition, the results provide information about the topography and relative orientation of residues involved in agonist binding in the serotonin 5-HT2 receptors.