1,2,3,4-tetrahydro-4,7,8-isoquinolinetriol hydrochloride | 85507-50-2

• 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: 1,2,3,4-tetrahydro-4,7,8-isoquinolinetriol hydrochloride
• 英文别名: 1,2,3,4-Tetrahydroisoquinoline-4,7,8-triol;hydrochloride
• CAS: 85507-50-2
• 化学式: C₉H₁₁NO₃*ClH
• 分子量: 217.652
• InChiKey: FPNDFBKHHHOAJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  168-172 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.7
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-amino>acetaldehyde dimethyl acetal 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 盐酸 、 甲醇 为溶剂， 反应 17.5h， 生成 1,2,3,4-tetrahydro-4,7,8-isoquinolinetriol hydrochloride
  参考文献：
  名称：

  Synthesis of tetrahydro-4,6,7-isoquinolinetriols and tetrahydro-4,7,8-isoquinolinetriols

  摘要：

  DOI：

  10.1021/jo00197a052

文献信息

• Fluorometric Determination of 1,2,3,4-Tetrahydro-6,7-dihydroxyisoquinoline in Biological Materials by HPLC.
  作者：Akira SHIRAHATA、Masanori YOSHIOKA、Zenzo TAMURA

  DOI：10.1248/cpb.45.1814

  日期：——

  In the belief that endogenous 1, 2, 3, 4-tetrahydro-6, 7-dihydroxyisoquinoline (DA-Fp) could be a potential marker involved in the etiology of various diseases such as Parkinsonism, we attempted to develop a fluorescence method for DA-Fp. It was synthesized by condensation of dopamine with formaldehyde according to an established method.Periodate was identified by screening from various oxidation reagents as a fluorescence reagent to DA-Fp. Optimal reaction conditions were obtained with 0.25 mM NaIO4 in 0.1 M phosphate buffer (pH 8.0) at 37°C for 15 min. The fluorescence spectrum of the derivative showed that we had found a new reaction specific for DA-Fp. This reaction we coupled on-line to high performance liquid chromatography (HPLC), which enabled us to achieve a highly sensitive method for determining DA-Fp. A working curve was linear from 2 to 800 pmol of DA-Fp per injection.To determine DA-Fp in biological materials, the pretreatment before HPLC was optimized by hydrolysis of its conjugate and suppression of the artifact with l-phenylephrine. Urinary excretion of DA-Fp in men was measured by this new present method. The urinary excretion of endogenous DA-Fp increased in a rabbit given L-DOPA. The DA-Fp concentration was determined in rat brain. The significance of DA-Fp in these biological materials is discussed and evaluated. We conclude that the present method will be useful for studying tetrahydroisoquinolines involved in meny diseases.

  由于认为内源性 1, 2, 3, 4-四氢-6, 7-二羟基异喹啉（DA-Fp）可能是帕金森病等多种疾病病因的潜在标志物，我们尝试开发一种 DA-Fp 的荧光方法。通过从各种氧化试剂中筛选，确定高碘酸盐为 DA-Fp 的荧光试剂。最佳反应条件是在 0.1 M 磷酸盐缓冲液（pH 8.0）中加入 0.25 mM NaIO4，在 37°C 下反应 15 分钟。衍生物的荧光光谱显示，我们发现了 DA-Fp 的新特异性反应。我们将该反应与高效液相色谱（HPLC）联用，从而实现了高灵敏度的 DA-Fp 检测方法。为了测定生物材料中的DA-Fp，我们对HPLC前的预处理进行了优化，水解了DA-Fp的共轭物，并用l-苯肾上腺素抑制了伪影。采用这种新方法测定了男性尿液中DA-Fp的排泄量。服用 L-DOPA 的兔子尿液中内源性 DA-Fp 的排泄量增加。测定了大鼠大脑中的 DA-Fp 浓度。我们讨论并评估了 DA-Fp 在这些生物材料中的意义。我们得出结论，本方法将有助于研究与多种疾病相关的四氢异喹啉类化合物。
• BATES, H. A., J. ORG. CHEM., 1983, 48, N 11, 1932-1934
  作者：BATES, H. A.

  DOI：——

  日期：——
• BATES, H. A.;GARELICK, J. S., J. ORG. CHEM., 1984, 49, N 23, 4552-4555
  作者：BATES, H. A.、GARELICK, J. S.

  DOI：——

  日期：——
• BATES H. A.; BAGHERI KOUROSH; VERTINO P. M., J. ORG. CHEM., 51,(1986) N 15, 3061-3063
  作者：BATES H. A.、 BAGHERI KOUROSH、 VERTINO P. M.

  DOI：——

  日期：——
• Synthesis of tetrahydro-4,6,7-isoquinolinetriols and tetrahydro-4,7,8-isoquinolinetriols
  作者：Hans Aaron Bates、Jeffrey S. Garelick

  DOI：10.1021/jo00197a052

  日期：1984.11