(3,4-dihydro-7-methoxy-2H-chromen-2-yl)methanol | 180716-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (3,4-dihydro-7-methoxy-2H-chromen-2-yl)methanol
• 英文别名: (7-methoxy-3,4-dihydro-2H-1-benzopyran-2-yl)methanol；(7-methoxy-3,4-dihydro-2H-chromen-2-yl)methanol
• CAS: 180716-14-7
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: PEYJKKSPJUOALY-UHFFFAOYSA-N

物化性质

• 沸点：
  332.3±30.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3,4-dihydro-7-methoxy-2H-chromen-2-yl)methanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 3-(7-Methoxy-chroman-2-ylmethyl-amino)-propanol
  参考文献：
  名称：

  New Generation Dopaminergic Agents. 1. Discovery of a Novel Scaffold Which Embraces the D₂ Agonist Pharmacophore. Structure−Activity Relationships of a Series of 2-(Aminomethyl)chromans

  摘要：

  A series of 2-(aminomethyl)chromans (2-AMCs) was synthesized and evaluated for their affinity and selectivity for both the high-and low-affinity agonist states (D-2(High) and D-2(Low), respectively) of the dopamine (DA) D-2 receptor. The 7-hydroxy-2-(aminomethyl)chroman moiety was observed to be the primary D-2 agonist pharmacophore. The 2-methylchroman moiety was discovered to be an entirely novel scaffold which could be used to access the D-2 agonist pharmacophore. Attaching various simple alkyl and arylalkyl side chains to the 7-hydroxy 2-AMC nucleus had significant effects on selectivity for the D-2(High) receptor vs the 5HT(1A) and alpha(1) receptors. A novel DA partial agonist, (R)-(-)-2-(benzylamino)methyl)chroman-7-ol [R-(-)-35c], was identified as having the highest affinity and best selectivity for the D-2(High) receptor vs the alpha(1) and 5HT(1A) receptors. Several regions of the 2-AMC nucleus were modified and recognized as potential sites to modulate the level of intrinsic activity. The global minimum conformer of the 7-hydroxy-2-AMC moiety was identified as fulfilling the McDermed model D-2 agonist pharmacophoric criteria and was proposed as the D-2 receptor-bound conformation. Structure-activity relationships gained from these studies have aided in the synthesis of D-2 partial agonists of varying intrinsic activity levels. These agents should be of therapeutic value in treating disorders resulting from hypo-and hyperdopaminergic activity, without the side effects associated with complete D-2 agonism or antagonism.

  DOI：

  10.1021/jm9703653
• 作为产物：
  描述：

  丹皮酚 在 锂硼氢 、 palladium 10% on activated carbon 、 氢气 、 sodium ethanolate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 123.0h， 生成 (3,4-dihydro-7-methoxy-2H-chromen-2-yl)methanol
  参考文献：
  名称：

  Bifunctional compounds targeting both D2 and non-α7 nACh receptors: Design, synthesis and pharmacological characterization

  摘要：

  We designed, prepared and tested a set of structural analogs 1-4 as new hybrid compounds by incorporating, through a common alkyl chain of variable length, the pharmacophoric elements of N-n-allcyl nicotinium salts (non-alpha 7 nicotinic acetylcholine receptors antagonists) and of 7-hydroxy-2-(aminomethyl)chromanes (dopaminergic D-2 receptor agonists). The target compounds, which were assayed in binding experiments and electrophysiological, functional and Erk1/2 activation tests, essentially combined the pharmacological profiles of their individual receptor ligands. Among the studied derivatives, hybrid 2, one of the shortest homologs, in addition to the antagonist nicotinic profile similar to the other three congeners, behaved as a high affinity ligand at the investigated heteromeric nAChRs and as a low efficacy agonist at D(2)Rs. These bifunctional derivatives represent novel pharmacological tools in the study of nicotine addiction. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.039

文献信息

• US5541199A
  申请人：——

  公开号：US5541199A

  公开（公告）日：1996-07-30
• US5670667A
  申请人：——

  公开号：US5670667A

  公开（公告）日：1997-09-23
• US5684039A
  申请人：——

  公开号：US5684039A

  公开（公告）日：1997-11-04
• US5756521A
  申请人：——

  公开号：US5756521A

  公开（公告）日：1998-05-26
• Bifunctional compounds targeting both D2 and non-α7 nACh receptors: Design, synthesis and pharmacological characterization
  作者：Carlo Matera、Luca Pucci、Chiara Fiorentini、Sergio Fucile、Cristina Missale、Giovanni Grazioso、Francesco Clementi、Michele Zoli、Marco De Amici、Cecilia Gotti、Clelia Dallanoce

  DOI：10.1016/j.ejmech.2015.06.039

  日期：2015.8

  We designed, prepared and tested a set of structural analogs 1-4 as new hybrid compounds by incorporating, through a common alkyl chain of variable length, the pharmacophoric elements of N-n-allcyl nicotinium salts (non-alpha 7 nicotinic acetylcholine receptors antagonists) and of 7-hydroxy-2-(aminomethyl)chromanes (dopaminergic D-2 receptor agonists). The target compounds, which were assayed in binding experiments and electrophysiological, functional and Erk1/2 activation tests, essentially combined the pharmacological profiles of their individual receptor ligands. Among the studied derivatives, hybrid 2, one of the shortest homologs, in addition to the antagonist nicotinic profile similar to the other three congeners, behaved as a high affinity ligand at the investigated heteromeric nAChRs and as a low efficacy agonist at D(2)Rs. These bifunctional derivatives represent novel pharmacological tools in the study of nicotine addiction. (C) 2015 Elsevier Masson SAS. All rights reserved.