3-methyl-6,7-methylenedioxy-1-(4-nitrophenyl)isoquinoline | 433716-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-methyl-6,7-methylenedioxy-1-(4-nitrophenyl)isoquinoline
• 英文别名: 7-methyl-5-(4-nitro-phenyl)-[1,3]dioxolo[4,5-g]isoquinoline；7-Methyl-5-(4-nitro-phenyl)-[1,3]dioxolo[4,5-g]isochinolin；1-(4-Nitrophenyl)-3-methyl-6,7-methylenedioxy-isoquinoline；7-methyl-5-(4-nitrophenyl)-[1,3]dioxolo[4,5-g]isoquinoline
• CAS: 433716-68-8
• 化学式: C₁₇H₁₂N₂O₄
• 分子量: 308.293
• InChiKey: BHVKBVYLGQUKEY-UHFFFAOYSA-N

物化性质

• 沸点：
  474.0±40.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  77.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyl-6,7-methylenedioxy-1-(4-nitrophenyl)isoquinoline 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以85%的产率得到1-(4-aminophenyl)-3-methyl-6,7-methylenedioxy-isoquinoline
  参考文献：
  名称：

  Synthesis and antitumor activity of 1,3-benzodioxole derivatives

  摘要：

  A series of 1,3-benzodioxoles (5-19) was synthesized and evaluated for their in vitro antitumor activity against human tumor cell lines. Some derivatives exhibited tumor growth inhibition activity. In particular, 6-(4-aminobenzoyl)-1,3-benzodioxole-5-acetic acid methyl ester 8, the most active compound of the series, possesses a significant growth inhibitory activity on 52 cell lines at concentrations ranging from 10(-7) to 10(-5) M. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01276-4
• 作为产物：
  描述：

  alpha-甲基-1,3-苯并二氧代-5-乙醇 在 phosphorus pentoxide 、 一水合肼 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 3-methyl-6,7-methylenedioxy-1-(4-nitrophenyl)isoquinoline
  参考文献：
  名称：

  A SIMPLE AND EFFICIENT SYNTHESIS OF GYKI 52466 AND GYKI 52895

  摘要：

  The synthesis of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (GYKI 52466. 1), the prototype of a series of noncompetitive AMPA receptor antagonists, and its 3,4-dihydroderivative (GYKI 52895, 2) is described. The title compounds have been prepared starting from safrole through a quite effective procedure.

  DOI：

  10.1081/scc-120002397

文献信息

• Synthesis of 2,3-Benzodiazepines and 2,3-Benzodiazepin-4-ones from Arynes and β-Diketones
  作者：Kentaro Okuma、Yukiko Tanabe、Noriyoshi Nagahora、Kosei Shioji

  DOI：10.1246/bcsj.20150064

  日期：2015.8.15

  2,3-Benzodiazepines were synthesized by two-step or one-pot reactions from aryne precursors. Reaction of 2-(trimethylsilyl)aryl triflates with β-diketones in the presence of CsF gave ortho-substitu...

  2,3-苯二氮卓类化合物是通过芳炔前体的两步或一锅反应合成的。在 CsF 存在下，2-（三甲基甲硅烷基）芳基三氟甲磺酸酯与 β-二酮反应得到邻位取代基...
• Yoshida, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 633,635, 639
  作者：Yoshida

  DOI：——

  日期：——
• A SIMPLE AND EFFICIENT SYNTHESIS OF GYKI 52466 AND GYKI 52895
  作者：Maria Zappalà、Silvana Grasso、Nicola Micale、Santina Polimeni、Carlo De Micheli

  DOI：10.1081/scc-120002397

  日期：2002.1.1

  The synthesis of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (GYKI 52466. 1), the prototype of a series of noncompetitive AMPA receptor antagonists, and its 3,4-dihydroderivative (GYKI 52895, 2) is described. The title compounds have been prepared starting from safrole through a quite effective procedure.
• Synthesis and antitumor activity of 1,3-benzodioxole derivatives
  作者：Nicola Micale、Maria Zappalà、Silvana Grasso

  DOI：10.1016/s0014-827x(02)01276-4

  日期：2002.9

  A series of 1,3-benzodioxoles (5-19) was synthesized and evaluated for their in vitro antitumor activity against human tumor cell lines. Some derivatives exhibited tumor growth inhibition activity. In particular, 6-(4-aminobenzoyl)-1,3-benzodioxole-5-acetic acid methyl ester 8, the most active compound of the series, possesses a significant growth inhibitory activity on 52 cell lines at concentrations ranging from 10(-7) to 10(-5) M. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.