1,2,3,4-四氢-6-甲氧基-7-异羟基喹啉盐酸盐 | 1078-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 1,2,3,4-四氢-6-甲氧基-7-异羟基喹啉盐酸盐
• 英文名称: 1,2,3,4-tetrahydro-6-methoxy-7-isoquinolinol hydrochloride
• 英文别名: 6-methoxy-1,2,3,4-tetrahydro-isoquinolin-7-ol; hydrochloride；6-Methoxy-1,2,3,4-tetrahydro-isochinolin-7-ol; Hydrochlorid；7-Hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride；6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol hydrochloride；6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol;hydrochloride
• CAS: 1078-26-8
• 化学式: C₁₀H₁₃NO₂*ClH
• 分子量: 215.68
• InChiKey: PMUXYTAVKHHBSG-UHFFFAOYSA-N

物化性质

• 熔点：
  248 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -2.98
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四氢-6-甲氧基-7-异羟基喹啉盐酸盐 在 磺酰氯 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 5,8-dichloro-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol hydrochloride
  参考文献：
  名称：

  WO2007/11290

  摘要：

  公开号：
• 作为产物：
  描述：

  4-羟基-3-甲氧基苄醇 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 1,2,3,4-四氢-6-甲氧基-7-异羟基喹啉盐酸盐
  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

• 一种治疗糖尿病的化合物
  申请人：四川好医生药业集团有限公司

  公开号：CN103435612B

  公开（公告）日：2016-03-09

  本发明提供了式I所示的化合物或其药学上可接受的盐、水合物或溶剂合物。本发明还提供了上述化合物或其药学上可接受的盐、水合物或溶剂合物的新用途。本发明制备的氘代化合物，可以明显改善肥胖患者体重、空腹血糖、转氨酶和空腹血清胰岛素，提高胰岛素敏感性，改善血脂指标和口服葡萄糖耐量；该类化合物体内吸收良好，生物利用度高，有利于药效的发挥，且半衰期延长，可以减少给药次数，降低毒副作用，为临床用药提供了安全可靠的新选择。式I。
• 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。
• Onda et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 409,410, 411
  作者：Onda et al.

  DOI：——

  日期：——
• Solid phase synthesis of tariquidar-related modulators of ABC transporters preferring breast cancer resistance protein (ABCG2)
  作者：Cristian Ochoa Puentes、Peter Höcherl、Matthias Kühnle、Stefanie Bauer、Kira Bürger、Günther Bernhardt、Armin Buschauer、Burkhard König

  DOI：10.1016/j.bmcl.2011.04.094

  日期：2011.6

  Aiming at structural optimization of potent and selective ABCG2 inhibitors, such as UR-ME22-1, from our laboratory, an efficient solid phase synthesis was developed to get convenient access to this class of compounds. 7-Carboxyisatoic anhydride was attached to Wang resin to give resin bound 2-aminoterephthalic acid. Acylation with quinoline-2- or -6-carbonyl chlorides, coupling with tetrahydroisoquinolinylethylphenylamine derivatives, cleavage of the carboxylic acids from solid support and treatment with trimethylsilydiazomethane gave the corresponding methyl esters. Among these esters highly potent and selective ABCG2 modulators were identified (inhibition of ABCB1 and ABCG2 determined in the calcein-AM and the Hoechst 33342 microplate assay, respectively). Interestingly, compounds bearing triethyleneglycol ether groups at the tetrahydroisoquinoline moiety (UR-COP77, UR-COP78) were comparable to UR-ME22-1 in potency but considerably more efficient (max inhibition 83% and 88% vs 60%, rel. to fumitremorgin c, 100%) These results support the hypothesis that solubility of the new ABCG2 modulators and of the reference compounds tariquidar and elacridar in aqueous media is the efficacy-limiting factor. (C) 2011 Elsevier Ltd. All rights reserved.
• 1,2,3,4-Tetrahydroisoquinoline antiarrhythmic agents
  申请人：Pfizer Limited

  公开号：EP0308059B1

  公开（公告）日：1992-09-09