1-methyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline | 61562-93-4

• 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: 1-methyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 6-hydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline；1-Methyl-1,2,3,4-tetrahydroisoquinolin-6-ol
• CAS: 61562-93-4
• 化学式: C₁₀H₁₃NO
• mdl: MFCD09970970
• 分子量: 163.219
• InChiKey: WTTCKKHZWWAOHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline 、 环己基异氰酸酯 生成 N-cyclohexyl-6-hydroxy-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(3-methoxyphenylethyl)acetamide 在 sodium tetrahydroborate 、 氢溴酸 、 phosphorus pentoxide 、 三氯氧磷 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 1-methyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Neuroprotective or neurotoxic activity of 1-methyl-1,2,3,4-tetrahydroisoquinoline and related compounds

  摘要：

  1-Methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ) 1 and various 5- or 6,7-substituted analogues were synthesized and assayed for neurotoxicity towards SH-SY5Y cells. Among mono-substituted derivatives of 1, hydroxyl substitution decreased the toxicity. while methoxyl substitution increased it. Disubstituted derivatives of 1, 5a and 5b, showed the opposite tendency. Hydroxy-1 MeTIQ derivatives were tested for neuroprotective activity, and 3b and 4b exhibited greater efficacy than 1. We suggest that hvdroxy-1MeTIQ derivatives. especially 4b, may have potential for the treatment of Parkinson's disease. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00583-3

文献信息

• [EN] CHROMEN-4-ONE DERIVATIVES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS DISEASE<br/>[FR] DÉRIVÉS DE CHROMEN-4-ONE POUR LE TRAITEMENT ET LA PROPHYLAXIE D'UNE MALADIE DUE AU VIRUS DE L'HÉPATITE B
  申请人：HOFFMANN LA ROCHE

  公开号：WO2020079106A1

  公开（公告）日：2020-04-23

  The present invention provides novel compounds having the general formula (I) wherein R1 to R6, and m are as described herein, compositions including the compounds and methods of using the compounds.

  本发明提供了具有通式（I）的新化合物，其中R1至R6和m如本文所述，包括该化合物的组合物以及使用该化合物的方法。
• [EN] NOVEL BIFUNCTIONAL MOLECULES FOR TARGETED PROTEIN DEGRADATION<br/>[FR] NOUVELLES MOLÉCULES BIFONCTIONNELLES POUR LA DÉGRADATION CIBLÉE DE PROTÉINES
  申请人：AMPHISTA THERAPEUTICS LTD

  公开号：WO2022129925A1

  公开（公告）日：2022-06-23

  The present disclosure relates to a novel class of bifunctional molecules that are useful in a targeted or selective degradation of a protein.

  本公开涉及一种新型的双功能分子，可用于有针对性或选择性地降解蛋白质。
• Interfacing Whole Cell Biocatalysis with a Biocompatible Pictet‐Spengler Reaction for One‐Pot Syntheses of Tetrahydroisoquinolines and Tryptolines**
  作者：Campbell M. Andersen、Luke D. Knudson、Dylan W. Domaille

  DOI：10.1002/cbic.202300464

  日期：2023.12.14

  Biocatalytic processes are highly selective and specific. However, their utility is limited by the comparatively narrow scope of enzyme‐catalysed transformations. To expand product scope, we are developing biocompatible processes that combine biocatalytic reactions with chemo‐catalysis in single‐flask processes. Here, we show that a chemocatalysed Pictet‐Spengler annulation can be interfaced with biocatalysed alcohol oxidation. This two‐step, one‐pot cascade reaction converts tyramine and aliphatic alcohols to tetrahydroisoquinoline alkaloids in aqueous buffer at mild pH. Tryptamine derivatives are also efficiently converted to tryptolines. Optimization of stoichiometry, pH, reaction time, and whole‐cell catalyst deliver the tetrahydroisouinolines and tryptolines in >90 % and >40 % isolated yield, respectively, with excellent regioselectivity.

  摘要 生物催化过程具有高度的选择性和特异性。然而，由于酶催化转化的范围相对较窄，其实用性受到了限制。为了扩大产品范围，我们正在开发将生物催化反应与化学催化相结合的生物兼容工艺。在这里，我们展示了化学催化的 Pictet-Spengler 环化反应可以与生物催化的醇氧化反应相结合。这种两步单锅级联反应可在温和 pH 值的水缓冲液中将酪胺和脂肪醇转化为四氢异喹啉生物碱。色胺衍生物也能高效地转化为色氨酸。对化学计量、pH 值、反应时间和全反应催化剂进行优化后，四氢异喹啉和色胺的分离产率分别为 90% 和 40%，并具有极佳的区域选择性。
• Canfield, Lesley M.; Crabb, Trevor A., Journal of Chemical Research, Miniprint, 1997, # 11, p. 2401 - 2416
  作者：Canfield, Lesley M.、Crabb, Trevor A.

  DOI：——

  日期：——
• Transaminase-Mediated Amine Borrowing <i>via</i> Shuttle Biocatalysis
  作者：Freya Taday、James Ryan、Rachel O’Sullivan、Elaine O’Reilly

  DOI：10.1021/acs.orglett.1c03320

  日期：2022.1.14