1-(3'-bromophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 96315-83-2

• 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-(3'-bromophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(3-bromophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 96315-83-2
• 化学式: C₁₇H₁₈BrNO₂
• 分子量: 348.239
• InChiKey: SFBPSVMVHHKKOC-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  438.1±45.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-(3'-bromophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 反应 1.5h， 生成 2-Acetyl-1-(3-bromophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives

  摘要：

  As a follow up of our previous structure-activity relationship and molecular modeling studies, we synthesized a novel series of 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as potential non-competitive AMPA receptor antagonists. When tested for their ability to prevent sound-induced seizures in DBA/2 mice, some of these novel compounds showed high anticonvulsant potency.

  DOI：

  10.1016/j.farmac.2003.10.003
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 4.0h， 生成 1-(3'-bromophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  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

• Aminomethylation of 1-Aryl-6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinolines by Dihydroquercetin
  作者：Sh. N. Zhurakulov、V. A. Babkin、E. I. Chernyak、S. V. Morozov、I. A. Grigor’ev、M. G. Levkovich、V. I. Vinogradova

  DOI：10.1007/s10600-015-1203-1

  日期：2015.1

  Mannich reaction of dihydroquercetin with a series of 1-aryl-6,7-dimethoxytetrahydroisoquinolines synthesized heterocyclic mono-and di-substituted conjugates of dihydroquercetin and N-hydroxymethyl isoquinoline derivatives.

  二氢槲皮素与一系列合成的1-芳基-6,7-二甲氧基四氢异喹啉进行的Mannich反应产生了二氢槲皮素的杂环单取代和双取代衍生物，以及N-羟甲基异喹啉的衍生物。
• 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
• Aminomethylation of Quercetin by Tetrahydroisoquinoline Derivatives and Their Biological Activity
  作者：Sh. N. Zhurakulov、D. A. Narbutaeva、A. M. Karakulova、F. M. Tursunkhodzhaeva、V. I. Vinogradova

  DOI：10.1007/s10600-023-04080-x

  日期：2023.7
• Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives
  作者：Rosaria Gitto、Roberta Caruso、Valerie Orlando、Silvana Quartarone、Maria Letizia Barreca、Guido Ferreri、Emilio Russo、Giovambattista De Sarro、Alba Chimirri

  DOI：10.1016/j.farmac.2003.10.003

  日期：2004.1

  As a follow up of our previous structure-activity relationship and molecular modeling studies, we synthesized a novel series of 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as potential non-competitive AMPA receptor antagonists. When tested for their ability to prevent sound-induced seizures in DBA/2 mice, some of these novel compounds showed high anticonvulsant potency.
• 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.