1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline | 91790-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline
• 英文别名: 2-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline；N-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline；interbrimine；6,7-dimethoxy-2-veratryl-1,2,3,4-tetrahydro-isoquinoline；6,7-Dimethoxy-2-veratryl-1,2,3,4-tetrahydro-isochinolin；Py-Tetrahydro-papaverin；2-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline
• CAS: 91790-53-3
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: YDCQKNFVLHDJKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline 在 palladium asbestos 作用下， 生成 罂粟碱
  参考文献：
  名称：

  Spaeth; Burger, Chemische Berichte, 1927, vol. 60, p. 705

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苄醇 在 三溴化磷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline
  参考文献：
  名称：

  Restraining the flexibility of the central linker in terameprocol results in constrained analogs with improved growth inhibitory activity

  摘要：

  The semi-synthetic lignan terameprocol inhibits the transcription of several inflammatory and oncogenic genes and has been evaluated for its anti-cancer properties. Here we investigated the effect of restricting the flexibility of the carbon linker connecting the terminal rings of terameprocol on its growth inhibitory activity. Conformational restriction was explored by introducing unsaturation, inserting polar entities with limited flexibility and cyclization of the connecting linker. Twenty three compounds were synthesized and evaluated on a panel of malignant human cells. The most promising compounds were those with non-polar linkers, as seen in butadiene 1a and the cyclized benzylideneindane analog 7. Both compounds were more potent than terameprocol on pancreatic BxPC-3 cells with GI(50) values of 3.4 and 8.1 mu M, respectively. Selected isomers of 1a (E,E) and 7 (Z) adopted low energy bent conformations that mimicked the low energy conformer of terameprocol. It is tempting to propose that conformational similarity to terameprocol may have contributed to their good activity. The scaffolds of 1a and 7 should be further investigated for their anticancer potential. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.014

文献信息

• Berberis alkaloids. XXII. Interbrinine and intebrimine ? New alkaloids from Berberis integerrima
  作者：A. Karimov、V. I. Vinogradova、R. Shakirov

  DOI：10.1007/bf00631016

  日期：——

  The known alkaloids reticuline, isoboldine, isocorydine, glaucine, armepavine, oxyacanthine, and heliamine and the new alkaloids intebrinine and intebrimine have been isolated from the total alkaloids of the leaves ofBerberis integerrima, and structures have been proposed for the latter two on the basis of spectral characteristics and independent synthesis.

  已从小檗叶片总生物碱中分离出已知的生物碱网状番荔枝碱、异花蕊碱、异花蓍碱、青花碱、紫杉碱、氧化棘黄素和海莨菪碱以及新的生物碱小檗碱和白莨菪碱，并在此基础上提出了后两者的结构。光谱特性和独立合成。
• Buck; Perkin; Stevens, Journal of the Chemical Society, 1925, vol. 127, p. 1472
  作者：Buck、Perkin、Stevens

  DOI：——

  日期：——
• CLXXXII.—isoQuinoline derivatives. Part II. The constitution of the reduction products of papaverine
  作者：Frank Lee Pyman

  DOI：10.1039/ct9099501610

  日期：——
• Majeed, Amera J.; Sainsbury, Malcolm; Hall, Stephen A., Journal of the Chemical Society. Perkin transactions I, 1984, # 4, p. 833 - 837
  作者：Majeed, Amera J.、Sainsbury, Malcolm、Hall, Stephen A.

  DOI：——

  日期：——
• Synthesis based on β-phenylethylamines. IV. Synthesis and antiarrhythmic activity of substituted phenylalkylamines and N-benzyltetrahydroisoquinolines
  作者：V. I. Vinogradova、T. I. Golodnyuk、N. Tulyaganov、M. S. Yunusov、N. Yu. Baratov

  DOI：10.1007/bf00630535

  日期：1993.5