1-(3',4'-dimethoxybenzyl)-6,7-dimethoxyisoquinolin-3-one | 38973-36-3

• 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-(3',4'-dimethoxybenzyl)-6,7-dimethoxyisoquinolin-3-one
• 英文别名: 1-(3',4'-dimethoxybenzyl)-6,7-dimethoxyisoquinoline-3-one；6,7-Dimethoxy-1-veratryl-3(2H)-isochinolon；1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-2H-isoquinolin-3-one；1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2H-isoquinolin-3-one
• CAS: 38973-36-3
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: MQIKBYUHEOZJDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3',4'-dimethoxybenzyl)-6,7-dimethoxyisoquinolin-3-one 在 盐酸 、 sodium hydroxide 、 氧气 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 1-(E)-(3',4'-dimethoxybenzylidene)-6,7-dimethoxyisoquinoline-3,4-dione
  参考文献：
  名称：

  Castedo, Luis; Estevez, Ramon J.; Saa, Jose M., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1469 - 1472

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苯基乙酸乙酯 在 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 1-(3',4'-dimethoxybenzyl)-6,7-dimethoxyisoquinolin-3-one
  参考文献：
  名称：

  Synthesis of 3-Oxo-2,3-Dihydroisoquinolines from Ethyl 2-Acylphenylacetates and Formamides

  摘要：

  1- and 1,3-substituted 3-oxo-2,3-dihydroisoquinolines 4 are obtained from ethyl 2-acylphenylacetates 3 and formamides.

  DOI：

  10.1080/00397919408011710

文献信息

• Acid-catalyzed cyclocondensation of nitriles. Part IV. Synthesis and spasmolytic activity of 1-substituted 3-aminoisoquinolines and their derivatives
  作者：A. V. Sereda、G. B. Lapa、I. E. Sukhov、L. F. Belova、S. Ya. Sokolov、A. I. Miroshnikov、O. N. Tolkachev

  DOI：10.1007/bf02464152

  日期：1997.4

  Biologically active compounds with an isoquinoline nucleus are widely used in medicine (papaverine, No-Spa, salsoline, etc.). Earlier, we have developed a simple and efficient method for the synthesis of 3-aminoisoquinolines and the corresponding 3-iminocarbonylamino derivatives [ I, 2]. The purpose of this work was to obtain acyl derivatives of 3-aminoisoquinolines, substituted at the amino group

  具有异喹啉核的生物活性化合物广泛用于医药（罂粟碱、No-Spa、沙索碱等）。早些时候，我们开发了一种简单有效的方法来合成 3-氨基异喹啉和相应的 3-亚氨基羰基氨基衍生物 [I, 2]。这项工作的目的是获得氨基取代的 3-氨基异喹啉的酰基衍生物，并研究 3-氨基异喹啉及其衍生物的解痉活性。最初的 3-氨基异喹啉 (IIIa-IIIc) 是使用先前描述的方法合成的 [1, 2]。该程序的第一步在于芳基乙腈的酸催化环缩合反应。这是一个三阶段过程（参见方案 1），包括中间体 Nimidoylnitrilium 离子 (II) 和 3-氨基异喹啉 (III) 的形成；反应机理在别处[1]中详细讨论过。尽管最终 3-氨基异喹啉基氨基酰亚胺 IV 的产率相当低 (50 - 72%)，但产品始终包含未反应的初始腈和 3-氨基异喹啉（二聚产物）[1, 2]。下面我们将证明增加第一阶段的持续时间会导致更完全的试剂消耗。色谱估计表明，反应物料中
• Radical cyclization to aporphines. A new, efficient total synthesis of the aporphine glaucine and the 4,5-dioxoaporphine pontevedrine, and the first total synthesis of 5-oxoaporphines.
  作者：Juan C. Estévez、M.Carmen Villaverde、Ramón J. Estévez、Luis Castedo

  DOI：10.1016/s0040-4020(01)85073-0

  日期：1994.2

  We describe the radical cyclization of bromobenzylisoquinolines and benzylisoquinolin-3-ones, which afford aporphines or the novel 5-oxoaporphines and 5-oxodehydroaporphines respectively. Oxidation of the latter compounds provides a new route to 4,5-dioxoaporphines.

  我们描述了溴苄基异喹啉和苄基异喹啉-3-酮的自由基环化作用，它们分别提供了磷灰石或新颖的5-氧杂卟啉和5-氧杂二氢卟啉。后一种化合物的氧化为4，5-二氧杂卟啉提供了一条新途径。
• 3(2H)-Isoquinolones therapeutic process
  申请人：Mead Johnson & Company

  公开号：US04015006A1

  公开（公告）日：1977-03-29

  New 2-substituted-3(2H)-isoquinolones and 2-substituted-3-alkoxyisoquinolines are disclosed. They are orally active hypotensives and peripheral vasodilators with an extended duration of action. Representative embodiments of this invention are 6,7-dimethoxy-2-methyl-1-veratryl-3(2H)-isoquinolone hydrochloride, 2-allyl-6,7-dimethoxy-1-veratryl-3(2H)-isoquinolone hydrochloride, 2-cyclopropyl-6,7-dimethoxy-1-veratryl-3(2H)-isoquinolone hydrochloride, 2-amino-6,7-dimethoxy-1-veratryl-3(2H)-isoquinolone hydrochloride, and 3-ethoxy-6,7-dimethoxy-1-veratrylisoquinoline.

  揭示了新的2-取代-3(2H)-异喹啉和2-取代-3-烷氧异喹啉。它们是口服活性低血压药和外周血管扩张剂，具有延长作用时间。本发明的代表性实施例包括6,7-二甲氧基-2-甲基-1-维拉特基-3(2H)-异喹啉盐酸盐、2-烯丙基-6,7-二甲氧基-1-维拉特基-3(2H)-异喹啉盐酸盐、2-环丙基-6,7-二甲氧基-1-维拉特基-3(2H)-异喹啉盐酸盐、2-氨基-6,7-二甲氧基-1-维拉特基-3(2H)-异喹啉盐酸盐和3-乙氧基-6,7-二甲氧基-1-维拉特基异喹啉。
• Discovery of a Series of Nonpeptide Small Molecules That Inhibit the Binding of Insulin-like Growth Factor (IGF) to IGF-Binding Proteins
  作者：Chen、Yun-Fei Zhu、Xin-Jun Liu、Zi-Xian Lu、Qiu Xie、Nicholas Ling

  DOI：10.1021/jm010304b

  日期：2001.11.1

  Insulin-like growth factors (IGF-I and II) play an important role in metabolic and mitogenic activities through stimulation of the IGF-I receptor on the cell surface. Although the concentration of IGF in blood and cerebrospinal fluid is quite high (> 100 nM), this large pool of IGF is biologically inactive because of its association with six distinct binding proteins, which form high-affinity complexes with IGF. Thus, inhibitors of IGF-binding proteins (IGFBPs), especially IGFBP-3, could potentially alter the distribution between the "free" and "bound" forms of IGF and thereby elevate biologically active IGF-I to exert a beneficial effect on those patients with diseases that respond to the application of exogenous IGF-I. Whereas IGF-I peptide variants, which bind to IGFBPs but not the IGF-I receptor, have been shown to be potent IGF/IGFBP inhibitors, small molecule nonpeptide IGF/IGFBP inhibitors have the potential advantages of oral bioavailability and flexible dosing regimen. Here we report the discovery of several isoquinoline analogues, exemplified by I and 2, which bind IGFBP-3 as well as other IGFBPs at low nanomolar concentrations. More importantly, both compounds were shown to be able to release biologically active IGF-I from the IGF-I/IGFBP-3 complex. These results point to the feasibility of developing orally active therapeutics to treat IGF-responsive diseases by optimization of the lead molecules 1 and 2.
• US4015006A
  申请人：——

  公开号：US4015006A

  公开（公告）日：1977-03-29