(S)-N-(4-methyl-3-pentenyl)-1,2,3,4-tetrahydroisoquinoline-3-carbaldehyde | 189081-05-8

• 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: (S)-N-(4-methyl-3-pentenyl)-1,2,3,4-tetrahydroisoquinoline-3-carbaldehyde
• 英文别名: (3S)-2-(4-methylpent-3-enyl)-3,4-dihydro-1H-isoquinoline-3-carbaldehyde
• CAS: 189081-05-8
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: WREISAVRCJCHKW-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-(4-methyl-3-pentenyl)-1,2,3,4-tetrahydroisoquinoline-3-carbaldehyde 在 氢氧化钾 、 4 A molecular sieve 、 二氯乙基铝 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 (8aR,14aS,14bS)-9,9-dimethyl-7,8,8a,9,14,14a,14b,15-octahydro-5H-benzo[b]isoquino[2,3-h]-1,7-naphthyridine-11-carboxylic acid
  参考文献：
  名称：

  Synthesis and DNA binding properties of novel benzo[b]isoquino[2,3-h]-naphthyridines

  摘要：

  作为一个关键步骤，通过 N-芳基亚胺的正式杂 Diels Alder 反应制备出了多种苯并[b]异喹啉并[2,3-h]萘啶类化合物。这些化合物在 C-11 处有不同的侧链，在 C-8a,C-14a 环交界处有顺式或反式构型。与寡核苷酸和多核苷酸相互作用的结合常数是通过紫外线吸收和熔化实验测定的。核磁共振实验（NOE）显示，顺式异构体显示出轻微的折叠结构，优先与富含 AT 的寡核苷酸的小沟结合。与此相反，反式异构体更倾向于富含 CG 的序列，从而形成异喹啉分子堆叠在双螺旋顶端的帽状复合物，这与扁平的形状一致，并且更倾向于喜树碱的 3′-末端。通过分子动力学（MD）计算，利用从 NOE 值得出的质子间距离建立了复合物的模型。对人类尤文肉瘤细胞系 RD-ES 和 CAD-ES1 进行了细胞毒性试验。

  DOI：

  10.1039/b503281d

文献信息

• Synthesis and in vitro cytotoxic activity of novel hexahydro-2H-pyrido[1,2-b]isoquinolines against human brain tumor cell lines
  作者：Axel Monsees、Sabine Laschat、Marc Hotfilder、Johannes Wolff、Klaus Bergander、Lothar Terfloth、Roland Fröhlich

  DOI：10.1016/s0960-894x(97)10114-7

  日期：1997.12

  1-Hetero-substituted hexahydro-2H-pyrido[1,2-b]isoquinolines 8 - 12 were prepared with varying diastereoselectivities in 6 steps from L-phenylalanine employing a Pictet-Spengler reaction and a Lewis acid-catalyzed cyclization of imines 7 as the key steps. Compounds 6, 8a,c, 9b and 12a,b were tested in vitro against human medulloblastoma D283 Med and glioblastoma A-172 and T98G cell lines. The largest cytotoxicities were observed for 8a (LC50 = 55, 29 and 42 mu mol l(-1)). (C) 1997 Elsevier Science Ltd.
• Synthesis and DNA binding properties of novel benzo[b]isoquino[2,3-h]-naphthyridines
  作者：Oliver Koepler、Stefania Mazzini、Maria Cristina Bellucci、Rosanna Mondelli、Angelika Baro、Sabine Laschat、Marc Hotfilder、Christophle Viseur、Wolfgang Frey

  DOI：10.1039/b503281d

  日期：——

  Several benzo[b]isoquino[2,3-h]-naphthyridines have been prepared via formal hetero-Diels Alder reaction of N-aryl imines as a key step. These compounds have different side chains at C-11, and a cis or trans configuration at the C-8a,C-14a ring junction. Binding constants for the interaction with oligonucleotides and polynucleotides were determined by UV absorption and melting experiments. NMR experiments (NOE) revealed that the cis isomers, showing a slightly folded structure, preferentially bind to the minor groove of AT-rich oligomers. In contrast, the trans isomers prefer the CG-rich sequences, leading to cap-complexes with the isoquinoline moiety stacked at the top of the double helix, in agreement with the flatter shape, and with a preference for the 3′-terminals, as found for camptothecins. Models of the complexes were built up by molecular dynamics (MD) calculations, by using the inter-proton distances derived from the NOE values. Cytotoxicity assays against human Ewing sarcoma cell lines RD-ES and CAD-ES1 were performed.

  作为一个关键步骤，通过 N-芳基亚胺的正式杂 Diels Alder 反应制备出了多种苯并[b]异喹啉并[2,3-h]萘啶类化合物。这些化合物在 C-11 处有不同的侧链，在 C-8a,C-14a 环交界处有顺式或反式构型。与寡核苷酸和多核苷酸相互作用的结合常数是通过紫外线吸收和熔化实验测定的。核磁共振实验（NOE）显示，顺式异构体显示出轻微的折叠结构，优先与富含 AT 的寡核苷酸的小沟结合。与此相反，反式异构体更倾向于富含 CG 的序列，从而形成异喹啉分子堆叠在双螺旋顶端的帽状复合物，这与扁平的形状一致，并且更倾向于喜树碱的 3′-末端。通过分子动力学（MD）计算，利用从 NOE 值得出的质子间距离建立了复合物的模型。对人类尤文肉瘤细胞系 RD-ES 和 CAD-ES1 进行了细胞毒性试验。