6,7-dimethoxy-1-(2-methoxy-phenyl)-1,2,3,4-tetrahydro-isoquinoline | 3161-12-4

• 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: 6,7-dimethoxy-1-(2-methoxy-phenyl)-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 6,7-Dimethoxy-1-(2-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
• CAS: 3161-12-4
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: RXFZPESWMNZRLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 4.0h， 生成 6,7-dimethoxy-1-(2-methoxy-phenyl)-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.02.040

文献信息

• o-Benzenedisulfonimide as a reusable acid catalyst for an easy, efficient, and green synthesis of tetrahydroisoquinolines and tetrahydro-β-carbolines through Pictet–Spengler reaction
  作者：Margherita Barbero、Stefano Bazzi、Silvano Cadamuro、Stefano Dughera

  DOI：10.1016/j.tetlet.2010.09.149

  日期：2010.12

  tetrahydro-β-carbolines, using the Pictet–Spengler reaction, was carried out in the presence of a catalytic amount of o-benzenedisulfonimide, which worked as a Brønsted acid organocatalyst. The reaction conditions were mild and green and good target product yields were achieved. The catalyst was easily recovered and purified, ready to be used in further reactions with economic and ecological advantages.

  使用Pictet-Spengler反应，在催化量的邻苯二磺酰亚胺的存在下进行四氢异喹啉和四氢β-咔啉的合成，该邻苯二磺酰亚胺用作布朗斯台德酸有机催化剂。反应条件温和绿色，并获得了良好的目标产物收率。该催化剂易于回收和纯化，准备用于经济和生态优势的进一步反应中。
• Evaluation of the Local Anesthetic Activity, Acute Toxicity, and Structure–Toxicity Relationship in Series of Synthesized 1-Aryltetrahydroisoquinoline Alkaloid Derivatives In Vivo and In Silico
  作者：Azizbek A. Azamatov、Sherzod N. Zhurakulov、Valentina I. Vinogradova、Firuza Tursunkhodzhaeva、Roaa M. Khinkar、Rania T. Malatani、Mohammed M. Aldurdunji、Antonio Tiezzi、Nilufar Z. Mamadalieva

  DOI：10.3390/molecules28020477

  日期：——

  first compound, 1-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3a), showed the highest toxicity with LD50 of 280 mg/kg in contrast to 1-(3'-bromo -4'-hydroxyphenyl)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3e) which proved to be the safest of the compounds studied. Its toxicity was 13.75 times lower than that of the parent compound 3a. All compounds investigated

  异喹啉生物碱是最常见的生物碱类之一，在治疗各种疾病方面表现出显着的作用。寻找降低这些分子毒性并增加其治疗范围的方法是当务之急。在这里，通过 Pictet-Spengler 反应，一步法合成一系列 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines，收率为 85-98%。这是使用 3,4-二甲氧基苯乙胺与取代的苯甲醛在三氟乙酸中沸腾的反应完成的。此外，通过 1-(3'- nitro-, 4'-nitrophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines with SnCl2 × 2H2O。所得物质的结构通过红外 (IR) 和核磁共振 (1H 和 13C NMR) 光谱得到证实。ADMET/TOPKAT in silico 研究得出结论，合成的化合物表现出可接受的药效学和药代动力学特性
• Brzezinska, Elzbieta, Acta poloniae pharmaceutica, 1996, vol. 53, # 5, p. 365 - 371
  作者：Brzezinska, Elzbieta

  DOI：——

  日期：——
• 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.