2-acetyl-6-methoxy-1,2,3,4-tetrahydro-isoquinolin-7-ol | 30597-81-0

• 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: 2-acetyl-6-methoxy-1,2,3,4-tetrahydro-isoquinolin-7-ol
• 英文别名: N-Acetyl-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline；2-Acetyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisochinolin；1-(7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethanone
• CAS: 30597-81-0
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: LYLWNZULCIRWKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基-3-甲氧基苄醇 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 2-acetyl-6-methoxy-1,2,3,4-tetrahydro-isoquinolin-7-ol
  参考文献：
  名称：

  Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide

  摘要：

  Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide-stimulated BV-2 microglial cells was determined. While NAMDA at 100 mu M inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by > 50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH4-dependent dimerization of the newly synthesized iNOS monomer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.033

文献信息

• 1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES HAVING EFFECTS OF PREVENTING AND TREATING DEGENERATIVE AND INFLAMMATORY DISEASES
  申请人：Hwang On-You

  公开号：US20100217003A1

  公开（公告）日：2010-08-26

  Provided are 7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline derivatives and synthesis methods thereof. The compounds significantly inhibit the production of nitrogen monoxide (NO) and superoxide in an activated microglial cell and expressions of TNF-α, IL-1β inducive NO synthase and cyclooxygenase-2 genes. They also prevent NF-kB shift to a nucleus, decrease reactive oxygen species (ROS), inhibit expression of GTP cyclohydrolase I gene and over-production of tetrahydrobiopterin (BH 4 ), and protect dopaminergic neurons from injury due to activated microglial cells. Consequently, the compounds are effective in treating inflammatory and neurodegenerative diseases.

  提供了7-羟基-6-甲氧基-1,2,3,4-四氢异喹啉衍生物及其合成方法。这些化合物显著抑制活化小胶质细胞中一氧化氮（NO）和超氧化物的产生，以及TNF-α、IL-1β诱导NO合成酶和环氧合酶-2基因的表达。它们还可以防止NF-kB转移到细胞核，降低活性氧自由基（ROS）的水平，抑制GTP环水合酶I基因的表达和四氢生物蝶呤（BH4）的过度产生，并保护多巴胺能神经元免受活化小胶质细胞引起的损伤。因此，这些化合物对于治疗炎症和神经退行性疾病具有有效性。
• Tetrahydroisoquinoline antiarrhythmic agents
  申请人：Pfizer Inc.

  公开号：US04882337A1

  公开（公告）日：1989-11-21

  Novel 4-amino-6,7-dimethoxy-2-(6,7-disubstituted-1,2,3,4-tetrahydroisoquinol-2-y l)quinoline compounds have been prepared, including their pharmaceutically acceptable salts and various novel key intermediates therefor. These compounds are useful in therapy as anti-arrhythmic agents and therefore, are of value in the treatment of various cardiac arrhythmias. Preferred compounds include 4-amino-6,7-dimethoxy-2-(6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinol-2 -yl)quinoline and 4-amino-6,7-dimethoxy-2-(7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinol-2 -yl)quinoline. Methods for preparing these compounds from known starting materials are provided.

  已制备出新颖的4-氨基-6,7-二甲氧基-2-(6,7-二取代-1,2,3,4-四氢异喹啉-2-基)喹啉化合物，包括其药学上可接受的盐和各种新颖的关键中间体。这些化合物在治疗中作为抗心律失常剂是有用的，因此在治疗各种心脏心律失常方面具有价值。优选化合物包括4-氨基-6,7-二甲氧基-2-(6-羟基-7-甲氧基-1,2,3,4-四氢异喹啉-2-基)喹啉和4-氨基-6,7-二甲氧基-2-(7-羟基-6-甲氧基-1,2,3,4-四氢异喹啉-2-基)喹啉。提供了从已知起始材料制备这些化合物的方法。
• 1,2,3,4-Tetrahydroisoquinoline antiarrhythmic agents
  申请人：Pfizer Limited

  公开号：EP0308059B1

  公开（公告）日：1992-09-09
• US4882337A
  申请人：——

  公开号：US4882337A

  公开（公告）日：1989-11-21
• US4965360A
  申请人：——

  公开号：US4965360A

  公开（公告）日：1990-10-23