5-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)pentan-1-amine | 916993-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 5-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)pentan-1-amine
• 英文别名: 5-(3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl)pentan-1-amine；5-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)pentan-1-amine
• CAS: 916993-89-0
• 化学式: C₁₆H₂₆N₂O₂
• 分子量: 278.395
• InChiKey: ITECHIVKJGAUMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  47.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)pentan-1-amine 在 Dowex 1X₈ chloride resin 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  In vitro activity of novel dual action MDR anthranilamide modulators with inhibitory activity at CYP-450

  摘要：

  Synthesis and in vitro cytotoxicity assays of new anthranilamide MDR modulators have been performed to assess their inhibition potency of the P-glycoprotein (P-gp) transporter. The aromatic spacer group between nitrogen atoms (N1 and N2) in the known inhibitor XR9576 was replaced with a flexible alkyl chain of 2 to 6 carbon atoms in length. 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline and their open-chain N-methylhomoveratrylamine counterparts were shown to be potent P-gp inhibitors. The maximal inhibition was obtained when using an ethyl or propyl spacer. Several compounds were more potent than verapamil and intrinsically less cytotoxic than XR9576. In addition, in vitro metabolism studies of 23a with a subset of human CYP-450 isoforms revealed that, unlike XR9576, 23a inhibited CYP3A4, an enzyme that colocalizes with P-gp in the intestine and contributes to tumor cell chemoresistance by enhancing the biodisposition of anticancer drugs such as paclitaxel toward metabolism. In this context, 22a might be a suitable candidate for further drug development.

  DOI：

  10.1016/j.bmc.2006.07.055
• 作为产物：
  描述：

  5-溴戊腈 在 lithium aluminium tetrahydride 、 四丁基碘化铵 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 5-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)pentan-1-amine
  参考文献：
  名称：

  Synthesis and in vitro evaluation of tetrahydroisoquinolines with pendent aromatics as sigma-2 (σ₂) selective ligands

  摘要：

  Sigma-2 选择性配体 - 一项结构活性关系研究表明，衍生物的效力和选择性增加，有潜力转化为放射标记配体。

  DOI：

  10.1039/c3ob42254b

文献信息

• 5-HT7 receptor antagonists
  申请人：Torrens Jover Antoni

  公开号：US20060040978A1

  公开（公告）日：2006-02-23

  The invention relates to compounds having pharmacological activity towards the 5-HT7 receptor, and more particularly to some tetrahydroisoquinoline substituted sulfonamide compounds, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use for the treatment and or prophylaxis of a disease in which 5-HT is involved, such as CNS disorders.

  这项发明涉及具有对5-HT7受体具有药理活性的化合物，更特别地涉及一些四氢异喹啉取代磺胺基化合物，以及制备这些化合物的过程，包括含有它们的药物组合物，并且用于治疗和/或预防涉及5-HT的疾病，如中枢神经系统紊乱。
• Zagórska, Agnieszka; Gryzło, Beata; Satała, Grzegorz, Acta poloniae pharmaceutica, 2016, vol. 73, # 2, p. 369 - 377
  作者：Zagórska, Agnieszka、Gryzło, Beata、Satała, Grzegorz、Bojarski, Andrzej J.、Głuch-Lutwin, Monika、Mordyl, Barbara、Kazek, Grzegorz、Pawłowski, Maciej

  DOI：——

  日期：——
• 5-ht7 receptor antagonists
  申请人：Torrens Jover Antoni

  公开号：US20090163542A1

  公开（公告）日：2009-06-25

  The invention relates to compounds having pharmacological activity towards the 5-HT7 receptor, and more particularly to some tetrahydroisoquinoline substituted sulfonamide compounds, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use for the treatment and or prophylaxis of a disease in which 5-HT is involved, such as CNS disorders.
• US7211585B2
  申请人：——

  公开号：US7211585B2

  公开（公告）日：2007-05-01
• US8188115B2
  申请人：——

  公开号：US8188115B2

  公开（公告）日：2012-05-29