6,7‐dihydroxy‐1,2,3,4‐tetrahydroisoquinolin‐2‐ium chloride | 42887-47-8

• 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: 6,7‐dihydroxy‐1,2,3,4‐tetrahydroisoquinolin‐2‐ium chloride
• 英文别名: 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride；1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrochloride；norsalsolinol；1,2,3,4-tetrahydro-isoquinoline-6,7-diol; hydrochloride；1,2,3,4-Tetrahydro-isochinolin-6,7-diol; Hydrochlorid；1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrochloride
• CAS: 42887-47-8
• 化学式: C₉H₁₁NO₂*ClH
• 分子量: 201.653
• InChiKey: ZAWPXTQFHFDESR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.28
• 重原子数：
  13
• 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：
  57.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7‐dihydroxy‐1,2,3,4‐tetrahydroisoquinolin‐2‐ium chloride 、 4-甲基-2-苯基-1,3-噻唑-5-碳酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以28%的产率得到N-(4-methyl-2-phenyl-1,3-thiazol-5-oyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  WO2008/95852

  摘要：

  公开号：
• 作为产物：
  描述：

  6,7-二甲氧基-1,2,3,4-四氢异喹啉 在 盐酸 作用下， 生成 6,7‐dihydroxy‐1,2,3,4‐tetrahydroisoquinolin‐2‐ium chloride
  参考文献：
  名称：

  Some Substituted Tetrahydroisoquinoline Hydrochlorides

  摘要：

  DOI：

  10.1021/ja01323a035

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。
• Synthesis and In Vitro Evaluation of C-7 and C-8 Luteolin Derivatives as Influenza Endonuclease Inhibitors
  作者：Robert Reiberger、Kateřina Radilová、Michal Kráľ、Václav Zima、Pavel Majer、Jiří Brynda、Martin Dračínský、Jan Konvalinka、Milan Kožíšek、Aleš Machara

  DOI：10.3390/ijms22147735

  日期：——

  The part of the influenza polymerase PA subunit featuring endonuclease activity is a target for anti-influenza therapies, including the FDA-approved drug Xofluza. A general feature of endonuclease inhibitors is their ability to chelate Mg2+ or Mn2+ ions located in the enzyme’s catalytic site. Previously, we screened a panel of flavonoids for PA inhibition and found luteolin and its C-glucoside orientin

  具有核酸内切酶活性的流感聚合酶 PA 亚基部分是抗流感治疗的靶点，包括 FDA 批准的药物 Xofluza。核酸内切酶抑制剂的一般特征是它们能够螯合位于酶催化位点的Mg 2+或 Mn 2+离子。以前，我们筛选了一组黄酮类化合物以抑制 PA，发现木犀草素及其 C-葡萄糖苷定向蛋白是有效的抑制剂。通过结构分析，我们确定 3',4'-二羟基苯基部分的存在是亚微摩尔抑制活性的关键特征。在这里，我们报告了后续调查的结果，该调查探索了木犀草素 C-7 和 C-8 位置的结构变化。实验 IC 50值由 AlphaScreen 技术确定。最有效的抑制剂是 C-8 衍生物，其抑制效力与木犀草素相当。木犀草素的 C-7 羟基部分的生物等排置换产生了一系列具有低一个数量级抑制效力的化合物。使用 X 射线晶体学，我们分别以 1.9 Å 和 2.2 Å 的分辨率解析了野生型 PA-N 末端结构域及其 I38T 突变体与
• COMPOUNDS AND METHODS FOR MODULATING RHO GTPASES
  申请人：Leblond Bertrand

  公开号：US20100120810A1

  公开（公告）日：2010-05-13

  The present invention relates to methods and compositions that affect the GTP-binding activity of members of the Rho family GTPases, preferably Rac GTPases (Rac1, Rac1b, Rac2 and/or Rac3).

  本发明涉及影响Rho家族GTP酶成员的GTP结合活性的方法和组合物，优选是Rac GTP酶（Rac1，Rac1b，Rac2和/或Rac3）。
• Tariquidar-Related Chalcones and Ketones as ABCG2 Modulators
  作者：Diana Peña-Solórzano、Matthias Scholler、Günther Bernhardt、Armin Buschauer、Burkhard König、Cristian Ochoa-Puentes

  DOI：10.1021/acsmedchemlett.8b00289

  日期：2018.8.9

  ABC transporters, including ABCG2, play a vital role in defending the human body against the vast range of xenobiotics. Even though this is beneficial for human health, these protein transporters have been implicated in the emerging resistance of cancer cells to a variety of structurally and functionally diverse anticancer drugs. In order to investigate their role in resistance, potent and selective ABCG2 modulators have been described in the literature. A leading class of modulators are the tariquidar analogues; however, their susceptibility to hydrolysis limits their applicable use. To overcome this, we synthesized a novel series of chalcone- and ketone-based compounds inspired by reported tariquidar analogues. Compounds were characterized and evaluated for their ABCG2 modulatory activity and ABC transporter selectivity. When compared to transporters ABCB1 and ABCC1, the chalcone-based compounds exhibited selectivity for ABCG2, while the ketone-based compounds showed only a slight preference for ABCG2. From the former series, chalcone 16d (UR-DP48) displayed similar activity to the reference fumitremorgin C, both producing comparable maximal effects. The compound exhibited marked antiproliferative activity, while cytotoxicity was less pronounced for the most active compound 17f from the ketone series. Chalcone-containing tariquidar analogues are promising modulators to aid in functional investigations of ABCG2 transporters.
• 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：——