6,7-dihydroxy-1-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

• 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-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(4-Methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: ZZWDDMRVGNYDGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-dihydroxy-1-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 、 四乙二醇二对甲苯磺酸酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以16%的产率得到
  参考文献：
  名称：

  基于天然产物的冠醚：合成及其抗癌潜力

  摘要：

  摘要 通过采用具有生物活性的天然结构，包括四氢异喹啉、白杨素和 biochanin-A 作为侧臂，制备了基于天然产物的新型冠醚。评估了所得冠支架对两种癌细胞系即 NCI-H460（非小肺癌）、MCF-7（乳腺癌）的抗癌潜力。比较研究表明，添加冠支架对亲本天然前体的抗增殖作用显着，尤其是对肺癌具有重要意义。与标准药物顺铂 ( IC 50= 19.00 ± 1.24 µM）。还检查了 NIH-3T3 细胞系的细胞毒性趋势，发现与亲本天然结构相比减少了。因此，这些发现可能为开发有效的抗癌药物开辟了一条新途径。 强调 已开发出四种基于天然产物的新型冠醚。 冠醚和天然前体的比较抗增殖筛选。 添加冠对天然产物的抗癌谱显示出显着效果。 冠的形成对于肺癌的可能性尤其重要。 Biochanin-A 衍生的冠醚发现比标准药物活性高三倍。

  DOI：

  10.1080/10286020.2021.1918118
• 作为产物：
  描述：

  盐酸多巴胺 、 4-甲氧基苯甲醛 在 potassium phosphate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以31%的产率得到6,7-dihydroxy-1-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  磷酸介导的四氢异喹啉生物碱的仿生合成。

  摘要：

  已经实现了在磷酸盐缓冲液中一锅法合成四氢异喹啉生物碱，并提出了反应机理。利用温和的反应条件可容易地得到一系列的异喹啉，包括降冰片碱。

  DOI：

  10.1039/c0cc05282e

文献信息

• The Catalytic Potential of<i>Coptis japonica</i>NCS2 Revealed - Development and Utilisation of a Fluorescamine-Based Assay
  作者：Thomas Pesnot、Markus C. Gershater、John M. Ward、Helen C. Hailes

  DOI：10.1002/adsc.201200641

  日期：2012.11.12

  The versatility and potential of a norcoclaurine synthase (NCS) from Coptis japonica NCS2 has been investigated, together with the development and application of a novel fluorescence-based high-throughput assay using nearly forty amines/aldehydes. The stereocontrol exerted by CjNCS2 on selected non-natural substrates has been determined, where the tetrahydroisoquinolines (THIAs) were formed as the

  研究了来自黄连NCS2的正月桂氨酸合成酶（NCS）的多功能性和潜力，以及使用近四十种胺/醛的新型荧光高通量测定方法的开发和应用。已经确定了Cj NCS2对选定的非天然底物施加的立体控制，其中天然氢去甲可可碱在> 95％ee中形成了四氢异喹啉（THIAs）作为（1 S）异构体。利用报告的黄藻NCS X射线晶体结构对涉及THIA机制中间体的对接计算，并与Cj结合NCS2筛选结果可进一步了解NCS的作用方式。这些发现表明，除了关键的活性位点残基K122和E110，D141对于酶促转化在机械上也是必不可少的。我们提出的机理进一步支持了NCS对醛底物的超强耐受性，其中醛从酶口袋中伸出。
• Phosphate mediated biomimetic synthesis of tetrahydroisoquinoline alkaloids
  作者：Thomas Pesnot、Markus C. Gershater、John M. Ward、Helen C. Hailes

  DOI：10.1039/c0cc05282e

  日期：——

  A one-pot synthesis of tetrahydroisoquinoline alkaloids in a phosphate buffer has been achieved, and a reaction mechanism proposed. The utilisation of mild reaction conditions readily afforded a range of isoquinolines, including norcoclaurine.

  已经实现了在磷酸盐缓冲液中一锅法合成四氢异喹啉生物碱，并提出了反应机理。利用温和的反应条件可容易地得到一系列的异喹啉，包括降冰片碱。
• 水溶性儿茶酚型四氢异喹啉类生物碱的分离 纯化方法
  申请人：山东大学

  公开号：CN110903241B

  公开（公告）日：2021-04-16

  本发明提供一种利用大孔树脂分离纯化水溶性儿茶酚型四氢异喹啉类生物碱的方法，所述水溶性儿茶酚型四氢异喹啉类生物碱具有式(I)所示结构：其中，R选自C1‑C5直链或支链的烷基、含有至少一个杂原子的脂肪环烷基、被至少一个取代基团取代的脂肪环烷基、苯基、苄基、被至少一个取代基团取代的苯基和被至少一个取代基团取代的苄基；所述杂原子选自N、O和S；所述取代基团选自取代或未被取代的C1‑C5直链或支链的烷基、C1‑C5支链或支链的烷氧基、硝基、卤素和羟基。该方法简便、经济、高效、环保。
• 1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro
  作者：Pi Cheng、Ning Huang、Zhi-Yong Jiang、Quan Zhang、Yong-Tang Zheng、Ji-Jun Chen、Xue-Mei Zhang、Yun-Bao Ma

  DOI：10.1016/j.bmcl.2008.02.040

  日期：2008.4

  A series of 1-aryl-6,7-dihydroxyl(methoxy)-1,2,3,4-tetrahydroisoquinolines (compounds 1-36) were synthesized via Pictet-Spengler cyclization. All the synthesized compounds were assayed for activities against HIV-1(IIIB) in C8166 cell cultures by MTT method for the first time. The results of the anti-HIV screening revealed that 6,7-dihydroxytetrahydroisoquinolines possessed higher selective index than 6,7-dimethoxyl analogs due to the significantly decreased cytotoxicities. Compounds 6, 24, and 36 showed potent anti-HIV activities with EC50 values of 8.2, 4.6, and 5.3 mu M respectively, and the cytotoxicities (CC50) of these three compounds were 784.3, 727.3, and 687.3 mu M, which resulted in SI values larger than 95, 159, and 130 respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis, Purification, and Selective β₂-AR Agonist and Bronchodilatory Effects of Catecholic Tetrahydroisoquinolines from <i>Portulaca oleracea</i>
  作者：Er-Lan Yang、Bin Sun、Zi-Yi Huang、Jian-Guang Lin、Bo Jiao、Lan Xiang

  DOI：10.1021/acs.jnatprod.9b00418

  日期：2019.11.22

  A green, biomimetic, phosphate-mediated Pictet-Spengler reaction was used in the synthesis of three catecholic tetrahydroisoquinolines, 1, 2, and 12, present in the medicinal plant Portulaca oleracea, as well as their analogues 3-11, 13, and 14, with dopamine hydrochloride and aldehydes as the substrates. AB-8 macroporous resin column chromatography was applied for purification of the products from the one-step high efficacy synthesis. It eliminated the difficulties in the isolation of catecholic tetrahydroisoquinolines from the aqueous reaction system and unreacted dopamine hydrochloride. Activity screening in CHO-K1/G alpha 15 cell models consistently expressing alpha(1B)-, beta(1)-, or beta(2)-adrenergic receptors indicated that 12 and 2, compounds that are present in P. oleracea, possessed the most potent beta(2)-adrenergic receptor agonist activity and 2 was a selective beta(2)-adrenergic receptor agonist at the concentration of 100 mu M. Both 12 and 2 exhibited dose-dependent bronchodilator effects on the histamine-induced contraction of isolated guinea-pig tracheal smooth muscle, with EC50 values of 0.8 and 2.8 mu M, respectively. These findings explain the scientific rationale of P. oleracea use as an antiasthmatic herb in folk medicine and provide the basis for the discovery of novel antiasthma drugs.