6-羟基-1,2,3,4-四氢异喹啉-1-甲酸 | 91523-50-1

• 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: 6-羟基-1,2,3,4-四氢异喹啉-1-甲酸
• 中文别名: 6-羟基-1,2,3,4-四氢-1-异喹啉羧酸
• 英文名称: 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
• 英文别名: 6-hydroxy-1,2,3,4-tetrahydroisoquinolin-2-ium-1-carboxylate
• CAS: 91523-50-1
• 化学式: C₁₀H₁₁NO₃
• mdl: MFCD04114842
• 分子量: 193.202
• InChiKey: WQTOOVAQGWLHKC-UHFFFAOYSA-N

物化性质

• 沸点：
  458.1±45.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  6-羟基-1,2,3,4-四氢异喹啉-1-甲酸 在 lithium aluminium tetrahydride 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 24.5h， 生成 1,2-bis(hydroxymethyl)-5,6-dihydro-8-methoxy-3-methylpyrrolo<2,1-a>isoquinoline
  参考文献：
  名称：

  Synthesis and murine antineoplastic activity of bis[carbamoyloxymethyl] derivatives of pyrrolo[2,1-a]isoquinoline

  摘要：

  The synthesis of 4,5-dihydropyrrolo[2,1-a]isoquinolines is reported. A key intermediate in the synthesis of 8-methoxy-4,5-dihydropyrrolo[2,1-a]isoquinolines, 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (6), was prepared by using a regiospecific phenolic cyclization reaction. The P388 lymphocytic activity is reported for 1,2-bis(hydroxymethyl)-5,6-dihydro-8-methoxy-3-methylpyrrolo [2,1-a]isoquinoline bis(isopropylcarbamate) (11a), 1,2-bis(hydroxymethyl)-5,6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a ]isoquinoline bis(cyclohexylcarbamate) (11b), 1,2-bis(hydroxymethyl)-5,6-dihydro-3-methylpyrrolo[2,1-a]isoqui nol ine bis(methylcarbamate) (13a), 1,2-bis(hydroxymethyl)-5,6-dihydro-3-methylpyrrolo [2,1-a]isoquinoline bis(ethylcarbamate) (13b), and 1,2-bis(hydroxymethyl)-5,6-dihydroxy-3-methylpyrrolo[2,1-a]isoq uin oline bis(cyclohexylcarbamate) (13c); all of the compounds were active. Compound 11a was tested in an expanded tumor panel and was shown to be active against B16 melanocarcinoma, CD8F1 mammary, L1210 lymphoid leukemia, colon 38, and MX-1 human tumor breast xenograft systems.

  DOI：

  10.1021/jm00376a017
• 作为产物：
  描述：

  间羟基苯甲醛 在 palladium on activated charcoal lithium aluminium tetrahydride 、 ammonium acetate 、 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-羟基-1,2,3,4-四氢异喹啉-1-甲酸
  参考文献：
  名称：

  Tetrahydroisoquinoline based sulfonamide hydroxamates as potent matrix metalloproteinase inhibitors

  摘要：

  The synthesis and MMP inhibitory activity of a series of tetrahydroisoquinoline based sulfonamide hydroxamates are described. In nine MMPs tested, most of the compounds display potent inhibition activity except for MMP-7. Some subtle isozyme selectivity is observed by varying the substituents at the 6- and 7-positions and aromatic ring of arylsulfonyl groups. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.026

文献信息

• Lactam derivatives as antiarrhythmic agents
  申请人：Bristol-Myers Squibb Company

  公开号：US06262068B1

  公开（公告）日：2001-07-17

  Lactam derivatives of the formula where X is —C(═O)NR3′—, —NR3′C(═O)—, —C(═NCN)NR3′—, —NR3′C(═NCN)—, —CH2NR3′—, —CH(alkyl)NR3′—, —CH(COOalkyl)NR3′—, —CH(CH2OH)NR3′—, —C(CH2Oalkyl)—; R1 is halo, alkyl, cycloalkyl, alkyl(cycloalkyl), aryl, (aryl)alkyl, (aryl)alkenyl, (aryl)alkynyl, O-alkyl, O-alkenyl, O-aryl, O-alky(aryl), O-alkyl(heterocyclo), COO-alkyl, C)-alkyl, CO-amino, CO-substituted amino, alkyl-CO-amino, alkyl-CO-substituted amino, NHCO-alkyl, NHCO-aryl, NHCO-alkyl(aryl), NHCO-alkyl(heterocyclo), N(alkyl)CO-alkyl, N(alkyl)CO-aryl, N(alkyl)CO-heterocyclo, N(alkyl)CO-alkyl(aryl), N(alkyl)CO-alkyl(heterocyclo); R2 is hydrogen, alkyl, halo, aryl, (aryl)alkyl, O-alkyl, amino, substituted amino; R3 and R3′ are the same or different and are independently selected from hydrogen, alkyl or alkyl(aryl); R4 which can be bonded to a ring carbon or nitrogen, is selected from hydrogen, alkyl, alkenyl, alky(aryl), alkyl(heterocyclo), cycloalkyl, alkyl(cycloalkyl), alkyl-(amino), alkyl-(substituted amino), alkyl-NHCO(alkyl), alkyl-NHCO(aryl), alkyl-NHCO(heterocyclo), alkyl-NHCO(alkylaryl), alkyl-NHCO(alkylheterocyclo); and n is an integer of 0 to 2. These compounds have been found to be useful in the treatment of arrhythmia.

  该公式的内酰胺衍生物，其中X为—C(═O)NR3′—，—NR3′C(═O)—，—C(═NCN)NR3′—，—NR3′C(═NCN)—，—CH2NR3′—，—CH(烷基)NR3′—，—CH(COO烷基)NR3′—，—CH(CH2OH)NR3′—，—C(CH2O烷基)—；R1为卤素，烷基，环烷基，烷基(环烷基)，芳基，(芳基)烷基，(芳基)烯基，(芳基)炔基，O-烷基，O-烯基，O-芳基，O-烷基(芳基)，O-烷基(杂环烷基)，COO-烷基，C)-烷基，CO-氨基，CO-取代氨基，烷基-CO-氨基，烷基-CO-取代氨基，NHCO-烷基，NHCO-芳基，NHCO-烷基(芳基)，NHCO-烷基(杂环烷基)，N(烷基)CO-烷基，N(烷基)CO-芳基，N(烷基)CO-杂环烷基，N(烷基)CO-烷基(芳基)，N(烷基)CO-烷基(杂环烷基)；R2为氢，烷基，卤素，芳基，(芳基)烷基，O-烷基，氨基，取代氨基；R3和R3′相同或不同，独立选择自氢，烷基或烷基(芳基)；R4可以与环烷基或氮键合，选择自氢，烷基，烯基，烷基(芳基)，烷基(杂环烷基)，环烷基，烷基(环烷基)，烷基-(氨基)，烷基-(取代氨基)，烷基-NHCO(烷基)，烷基-NHCO(芳基)，烷基-NHCO(杂环烷基)，烷基-NHCO(烷基芳基)，烷基-NHCO(烷基杂环烷基)；n为0至2的整数。这些化合物已被发现在心律失常的治疗中具有用途。
• CARBON-LINKED TETRAHYDRO-PYRAZOLO-PYRIDINE MODULATORS OF CATHEPSIN S
  申请人：Ameriks Michael K.

  公开号：US20080200454A1

  公开（公告）日：2008-08-21

  Carbon-linked tetrahydro-pyrazolo-pyridine compounds are described, which are useful as cathepsin S modulators. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by cathepsin S activity, such as psoriasis, pain, multiple sclerosis, atherosclerosis, and rheumatoid arthritis.

  描述了与碳相连的四氢吡唑吡啶化合物，这些化合物可作为cathepsin S调节剂。这些化合物可用于制备药物组合物和治疗疾病状态、疾病和病况的方法，这些疾病状态、疾病和病况是由cathepsin S活性介导的，如银屑病、疼痛、多发性硬化症、动脉粥样硬化和类风湿性关节炎。
• Tetrahydroisoquinoline analogs as modulators of chemokine receptor activity
  申请人：Bristol-Myers Squibb Co.

  公开号：US06649606B1

  公开（公告）日：2003-11-18

  Tetrahydroisoquinoline analogs are provided which are modulators of chemokine receptor activity. The tetrahdroisoquinoline analogs thereof have the structure wherein R1, R2, R3, R3a, X1, X2, X3, X4, m, n and p are as described herein.

  提供了四氢异喹啉类似物，它们是趋化因子受体活性的调节剂。其四氢异喹啉类似物具有以下结构，其中R1、R2、R3、R3a、X1、X2、X3、X4、m、n和p如本文所述。
• Synthesis of novel (benzimidazolyl)isoquinolinols and evaluation as adenosine A1 receptor tools
  作者：Sameek Singh、Samantha L. Cooper、Jacqueline R. Glenn、Jessica Beresford、Lydia R. Percival、Joel D. A. Tyndall、Stephen J. Hill、Laura E. Kilpatrick、Andrea J. Vernall

  DOI：10.1039/c7ra13148h

  日期：——

  G protein-coupled receptors (GPCRs) constitute the largest family of transmembrane receptors in eukaryotes. The adenosine A1 receptor (A1AR) is a class A GPCR that is of interest as a therapeutic target particularly in the treatment of cardiovascular disease and neuropathic pain. Increased knowledge of the role A1AR plays in mediating these pathophysiological processes will help realise the therapeutic

  G 蛋白偶联受体 (GPCRs) 构成真核生物中最大的跨膜受体家族。腺苷 A 1受体 (A 1 AR) 是一种 A 类 GPCR，其作为治疗靶标是令人感兴趣的，特别是在治疗心血管疾病和神经性疼痛中。增加对 A 1 AR 在介导这些病理生理过程中的作用的了解将有助于实现该受体的治疗潜力。由于缺乏诸如选择性荧光探针等工具来研究 A 1 AR，因此我们设计了一系列与荧光染料结合的（苯并咪唑基）异喹啉醇（31-35、42-43）。报道了一种通过用 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 和大气氧氧化从四氢异喹啉醇合成异喹啉醇的改进方法。这种合成方法比以前的金属基制备异喹啉和异喹啉的方法具有优势，异喹啉和异喹啉是许多生物活性化合物和天然产物中发现的重要支架。我们报告了（苯并咪唑基）异喹啉醇化合物类的首次合成，但是荧光缀合物作为 A 1 AR 荧光配体并不成功。
• Chemoenzymatic Approach to ( <i>S</i> )‐1,2,3,4‐Tetrahydroisoquinoline Carboxylic Acids Employing D‐Amino Acid Oxidase
  作者：Shuyun Ju、Mingxin Qian、Gang Xu、Lirong Yang、Jianping Wu

  DOI：10.1002/adsc.201900178

  日期：2019.7.2

  Optically pure 1,2,3,4‐tetrahydroisoquinoline carboxylic acids constitute an important class of building blocks for the synthesis of natural products and synthetic pharmaceuticals. However, redox deracemization of racemic 1,2,3,4‐tetrahydroisoquinoline carboxylic acids as an attractive method is still challenging for the lack of suitable oxidoreductases. Herein, a D‐amino acid oxidase from Fusarium

  光学纯的1,2,3,4-四氢异喹啉羧酸是合成天然产物和合成药物的重要组成部分。然而，由于缺少合适的氧化还原酶，外消旋的1,2,3,4-四氢异喹啉羧酸的氧化还原脱硫仍然是一个有吸引力的方法。本文中，通过基因组挖掘，利用了镰刀菌M-0718（Fs DAAO）的D-氨基酸氧化酶，具有广泛的底物范围和优异的对映选择性，并用于动力学拆分多个外消旋的1-3位羧基取代的四氢异喹啉以得到相应的（小号具有优异的对映体过量（） -对映体EE）值（最高> 99％）。通过在一锅中将Fs DAAO与氨硼烷结合使用，这些外消旋的羧基取代的四氢异喹啉可进行脱硝，转化率高达ee > 98％和ee > 99％。外消旋的1,2,3,4-四氢异喹啉-1-羧酸和1,2,3,4-四氢异喹啉-3-羧酸的制备规模脱硝反应也显示出良好的分离收率（分别为82％和73％ ），且ee > 99％。我们的研究为合成对映体纯的1,2,3,4-四氢