(S)-(-)-1-(α-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide | 626252-74-2

• 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: (S)-(-)-1-(α-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide
• 英文别名: (S)-(-)-YS-49 hydrobromide；(S)-6,7-dihydroxy-1-(α-naphthylmethyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide salt；(S)-6,7-dihydroxy-1-(α-naphthylmethyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide；CKD-712 hydrobromide；(1S)-1-(naphthalen-1-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrobromide
• CAS: 626252-74-2
• 化学式: BrH*C₂₀H₁₉NO₂
• 分子量: 386.288
• InChiKey: JXFRKNGQHAAJKY-FERBBOLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.5
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-(α-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide 以51的产率得到(S)-(-)-1-(α-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Novel enantiomers of etrahydroisoquinoline derivatives and theirpharmaceutically acceptable salts, their preparations and pharmaceutical compositions

  摘要：

  该披露涉及四氢异喹啉衍生物的新手性异构体及其药学上可接受的盐、其制备和制药组合物。提供了四氢异喹啉衍生物的手性异构体，其对于刺激心率和降压活性、抑制血小板聚集活性以及对可诱导的一氧化氮合酶具有抑制作用是有用的。四氢异喹啉衍生物的手性异构体及其药学上可接受的盐对于治疗充血性心力衰竭、高血压、血栓形成、炎症、败血症、心脏功能不全和弥漫性血管内凝血是有效的。

  公开号：

  US20060058346A1
• 作为产物：
  描述：

  (S)-6,7-dimethoxy-1-(α-naphthylmethyl)-1,2,3,4-tetrahydroisoquinoline 在 borontribromide methylsulfide 、 甲醇 作用下， 以 氯仿 为溶剂， 反应 37.0h， 以85%的产率得到(S)-(-)-1-(α-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide
  参考文献：
  名称：

  METHOD FOR RESOLVING ENANTIOMERS FROM RACEMIC MIXTURE HAVING CHIRAL CARBON IN ALPHA POSITION OF NITROGEN

  摘要：

  揭示了一种简化的方法，通过将含有手性碳的混合物溶解在氮的α位和氨基酸中，制备出对映异构盐来分离对映体，而不使用催化剂或酶，显著提高光学纯度。此外，本发明可以大量制备对映体，而无需使用昂贵的催化剂或控制应用酶的反应条件。

  公开号：

  US20090036679A1

文献信息

• [EN] NOVEL ENANTIOMERS OF TETRAHYDROISOQUINOLINE DERIVATIVES AND THEIR PHARMACEUTICALLY ACCEPTABLE SALTS, THEIR PREPARATIONS AND PHARMACEUTICAL COMPOSITIONS<br/>[FR] NOUVEAUX ENANTIOMERES DE DERIVES DE TETRAHYDROISOQUINOLINE ET LEURS SELS PHARMACEUTIQUEMENT ACCEPTABLES, PREPARATIONS ET COMPOSITIONS PHARMACEUTIQUES DE CES DERNIERS
  申请人：YUN-CHOI HYE-SOOK

  公开号：WO2003095426A1

  公开（公告）日：2003-11-20

  The disclosure concerns novel enantiomers of tetrahydroisoquinoline derivatives and their pharmaceutically acceptable salts, their preparations and pharmaceutical compositions. The enantiomers of tetrahydroisoquinoline derivatives are provided which are useful in stimulating heart rate and hypotensive activity, inhibitory activity against platelet aggregation, and suppressive against inducible NO synthase. The enantiomers of tetrahydroisoquinoline derivatives and their pharmaceutically acceptable salts are effective for treating congestive heart failure, hypertension, thrombosis, inflammation, septicemia, cardiac insufficiency, and disseminated intravascular coagulopathy.

  该披露涉及四氢异喹啉衍生物的新对映体及其药用盐，它们的制备和药物组合物。所提供的四氢异喹啉衍生物的对映体在刺激心率和降压活性、抑制血小板聚集活性以及对诱导型NO合酶的抑制方面具有用途。四氢异喹啉衍生物的对映体及其药用盐对治疗充血性心力衰竭、高血压、血栓形成、炎症、败血症、心脏功能不全和播散性血管内凝血症具有有效性。
• Enantioselective synthesis of (R)-(+)- and (S)-(−)-higenamine and their analogues with effects on platelet aggregation and experimental animal model of disseminated intravascular coagulation
  作者：Mi Kyung Pyo、Duck-Hyung Lee、Doo-Hyun Kim、Ji-Hye Lee、Jong-Cheon Moon、Ki Churl Chang、Hye Sook Yun-Choi

  DOI：10.1016/j.bmcl.2008.05.094

  日期：2008.7

  Optically active tetrahydroisoquinoline alkaloids, (R)-(+)-higenamine (1R) and (S)-(-)-higenamine (1 S), and their optically active 1-naphthylmethyl analogues (2 and 3), were synthesized by enantioselective hydrogenation of the corresponding dihydroisoquinoline intermediates 7 as a key step. The evaluation of the platelet anti-aggregation effect demonstrated clearly that the (S)-(-)-enantiomers, 1S, 2S, and 3S, had higher inhibitory potency than the corresponding (R)-(+)-antipodes, 1R, 2R, and 3R, respectively, to platelet aggregation induced by epinephrine. 1S enantiomer was superior to the corresponding 1R enantiomer in attenuating all of the disseminated intravascular coagulation (DIC) and multiple organ failure (MOF) parameters tested, while the S enantiomers 2S and 3S ameliorated some of the DIC and MOF parameters more effectively than the corresponding antipodes 2R and 3R. (c) 2008 Published by Elsevier Ltd.
• WO2007/91753
  申请人：——

  公开号：——

  公开（公告）日：——
• NOVEL ENANTIOMERS OF TETRAHYDROISOQUINOLINE DERIVATIVES AND THEIR PHARMACEUTICALLY ACCEPTABLE SALTS, THEIR PREPARATIONS AND PHARMACEUTICAL COMPOSITIONS
  申请人：Yun-Choi, Hye-Sook

  公开号：EP1507764A1

  公开（公告）日：2005-02-23
• EP1507764A4
  申请人：——

  公开号：EP1507764A4

  公开（公告）日：2005-06-22