butyl-(7-methoxy-chroman-2-ylmethyl)-amine | 198986-28-6

• 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: butyl-(7-methoxy-chroman-2-ylmethyl)-amine
• 英文别名: N-[(7-methoxy-3,4-dihydro-2H-chromen-2-yl)methyl]butan-1-amine
• CAS: 198986-28-6
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: VFSIJPMIRCTYKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  butyl-(7-methoxy-chroman-2-ylmethyl)-amine 以 aqueous HBr 为溶剂， 生成 2-Butylaminomethyl-chroman-7-ol
  参考文献：
  名称：

  Chroman-2-ylmethylamino derivatives

  摘要：

  式子为##STR1##的化合物，其中R是1到6个碳原子的直链或支链烷基，1到6个碳原子的羟基烷基或3到8个碳原子的环烷基；或其药学上可接受的盐是多巴胺合成和释放的抑制剂，可用于治疗精神分裂症、帕金森病、图雷特综合症、酗酒、可卡因成瘾和类似药物成瘾。

  公开号：

  US05684039A1
• 作为产物：
  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 butyl-(7-methoxy-chroman-2-ylmethyl)-amine
  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

文献信息

• Chroman-2-ylmethylamino derivatives
  申请人：American Home Products Corporation

  公开号：US05684039A1

  公开（公告）日：1997-11-04

  Compounds of the formula: ##STR1## in which R is a straight or branched chain alkyl group of 1 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms or a cycloalkyl group of 3 to 8 carbon atoms; or a pharmaceutically acceptable salt thereof are inhibitors of dopamine synthesis and release, useful in the treatment of schizophrenia, Parkinson's Disease, Tourette's Syndrome, alcohol addiction, cocaine addiction, and addiction to analagous drugs.

  式子为##STR1##的化合物，其中R是1到6个碳原子的直链或支链烷基，1到6个碳原子的羟基烷基或3到8个碳原子的环烷基；或其药学上可接受的盐是多巴胺合成和释放的抑制剂，可用于治疗精神分裂症、帕金森病、图雷特综合症、酗酒、可卡因成瘾和类似药物成瘾。
• US5684039A
  申请人：——

  公开号：US5684039A

  公开（公告）日：1997-11-04
• 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
  作者：Richard E. Mewshaw、Joseph Kavanagh、Gary Stack、Karen L. Marquis、Xiaojie Shi、Michael Z. Kagan、Michael B. Webb、Alan H. Katz、Anna Park、Young H. Kang、Magid Abou-Gharbia、Rosemary Scerni、Theodore Wasik、Luz Cortes-Burgos、Taylor Spangler、Julie A. Brennan、Michael Piesla、Hossein Mazandarani、Mark I. Cockett、Rafal Ochalski、Joseph Coupet、Terrance H. Andree

  DOI：10.1021/jm9703653

  日期：1997.12.1

  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.