1-(4-硝基苯磺酰基)-1,2,3,4-四氢喹啉 | 182565-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 1-(4-硝基苯磺酰基)-1,2,3,4-四氢喹啉
• 英文名称: 1-(4-nitrobenzenesulfonyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-[(4-Nitrophenyl)sulfonyl]-1,2,3,4-tetrahydroquinoline；1-(4-nitrophenyl)sulfonyl-3,4-dihydro-2H-quinoline
• CAS: 182565-33-9
• 化学式: C₁₅H₁₄N₂O₄S
• 分子量: 318.353
• InChiKey: ZIGIWEQTIQZFBN-UHFFFAOYSA-N

物化性质

• 熔点：
  116.5-117.5 °C
• 沸点：
  505.3±60.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-硝基苯磺酰基)-1,2,3,4-四氢喹啉 在 potassium carbonate 、 苯硫酚 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以99%的产率得到1,2,3,4-四氢喹啉
  参考文献：
  名称：

  Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo)arenes

  摘要：

  Sulfonamides of primary amines bearing an aromatic ring at the gamma-position were treated with (diacyloxyiodo)arenes and:iodine under irradiation conditions with;a tungsten-lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields. Here, the reactivity depends on the Z-group (protecting group) of the starting amides. Under the same reaction conditions, some sulfonamides were treated with (diacetoxyiodo)benzene and iodine in the presence of aromatics to give the corresponding N-arylated amides. These reactions proceed through the intramolecular and intermolecular amidations onto aromatic rings via the sulfonamidyl radicals formed.

  DOI：

  10.1021/jo980450y
• 作为产物：
  描述：

  N-[3-(2-Iodo-phenyl)-propyl]-4-nitro-benzenesulfonamide 在 copper(l) iodide 、 cesium acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以99%的产率得到1-(4-硝基苯磺酰基)-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  芳基卤化物的温和铜介导的分子内胺化

  摘要：

  发现碘化铜和醋酸铯的独特组合在温和条件下介导芳基卤化物的分子内胺化。该反应在室温下用伯胺或 N-苄基胺进行，在适度升高的温度下用其他胺衍生物进行。该反应已应用于形成 5、6 和 7 元环。值得注意的是，保留了间位的卤素，提供了优于钯催化系统的决定性优势。

  DOI：

  10.1055/s-2002-19782

文献信息

• Aromatic Sulfonamides Containing a Condensed Piperidine Moiety as Potential Oxidative Stress-Inducing Anticancer Agents
  作者：Ramóna Madácsi、Iván Kanizsai、Liliána Fehér、Márió Gyuris、Béla Ózsvári、András Erdélyi、János Wölfling、László Puskás

  DOI：10.2174/1573406411309070004

  日期：2013.8.1

  A 30-membered piperidine ring-fused aromatic sulfonamide library was synthetized, including N-arylsulfonyl 1,2,3,4-tetrahydroquinolines, 1,2,3,4-tetrahydroisoquinolines and 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoles. The compounds induced oxidative stress and glutathione depletion in HT168 melanoma and K562 leukemia cells and in micromolar concentrations exerted cytotoxic effects. Among the tested sulfonamides, compounds 21, 22, 23, 35 and 41 exhibited 100% cytotoxic effects with low (< 10 µM) EC50 values on K562 cells. The cytotoxicity of lead compound 22 was investigated in 24 different cancer cell lines, and it was found to be active against leukemia, melanoma, glioblastoma, and liver, breast and lung cancer cells, as confirmed by classical biochemical and holographic microscopic analyses.

  合成了一组包含30个成员的哌啶环融合芳香磺酰胺库，包括N-芳基磺酰基的1,2,3,4-四氢喹啉、1,2,3,4-四氢异喹啉和2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚。该化合物在HT168黑色素瘤细胞和K562白血病细胞中诱导了氧化应激和谷胱甘肽耗竭，并在微摩尔浓度下表现出细胞毒性效应。在测试的磺酰胺中，化合物21、22、23、35和41在K562细胞上表现出100%的细胞毒性效应，且EC50值较低（< 10 µM）。在24种不同癌细胞系中研究了主要化合物22的细胞毒性，结果发现其对白血病、黑色素瘤、胶质母细胞瘤，以及肝癌、乳腺癌和肺癌细胞均具有活性，这一点通过经典的生化和全息显微镜分析得到了确认。
• Design, Synthesis and 3-D Characterization of 1-Benzenesulfonyl-1,2,3,4- Tetrahydroquinolines as Lead Scaffold for Antiparasitic Drug
  作者：R.J. Pagliero、A.B. Pierini、R. Brun、M.R. Mazzieri

  DOI：10.2174/157018010791306614

  日期：2010.7.1

  Ten 1-benzenesulfonyl-1,2,3,4-tetrahydroquinoline (BSTHQ) were synthesized and characterized and their antiprotozoal activities were investigated. This small library was designed by combining two chemical moieties that are known to be biologically active by itself. The BS group seems to be favorable for the antiparasitic activity, since the derivatives presented lower IC50 value than the precursor heterocycle. Most compounds were moderately active against T cruzi, but 3 showed a promising IC50 value (9.76μM) with low cytotoxicity (L6). Also, 3, 6 and 9 showed interesting activity and reasonable selectivity against P. falciparum. These derivatives are considered as lead scaffolds and merit further exploration through structure optimization.

  合成并表征了十种1-苯磺酰基-1,2,3,4-四氢喹啉（BSTHQ），并研究了它们的抗原虫活性。这个小型化合物库是通过结合两种已知具有生物活性的化学基团设计的。BS基团似乎对抗寄生虫活性是有利的，因为这些衍生物的IC50值低于前体杂环化合物。大多数化合物对T. cruzi表现出中等活性，但3呈现出有希望的IC50值（9.76μM）且细胞毒性较低（L6）。此外，3、6和9对P. falciparum表现出有趣的活性和合理的选择性。这些衍生物被认为是先导骨架，值得通过结构优化进行进一步探索。
• Facile Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxides and Related Reaction with 1,3-Diiodo-5,5-dimethylhydantoin under Photochemical Conditions
  作者：Hideo Togo、Atsushi Moroda、Shusuke Furuyama

  DOI：10.1055/s-0028-1216725

  日期：——

  3,4-Dihydro-2,1-benzothiazine 2,2-dioxides were easily obtained in good yields by the reaction of N-methyl 2-arylethane-sulfonamides with 1,3-diiodo-5,5-dimethylhydantoin (D1H) under irradiation with a tungsten lamp. When N-benzyl 2-phenylethane-sulfonamide was treated with DIH under the same conditions, the corresponding N-benzyl 3,4-dihydro-2,1-benzothiazine 2,2-dioxide was obtained in good yield

  通过 N-甲基 2-芳基乙烷-磺酰胺与 1,3-二碘-5,5-二甲基乙内酰脲 (D1H) 在下反应，3,4-二氢-2,1-苯并噻嗪 2,2-二氧化物很容易以良好的收率获得用钨灯照射。N-苄基2-苯基乙磺酰胺在相同条件下用DIH处理，以良好的收率得到相应的N-苄基3,4-二氢-2,1-苯并噻嗪2,2-二氧化物，N-苄基在 Pd(OH) 2 存在下用氢气处理很容易去除基团。另一方面，在钨灯照射下用 DIH 处理 N-3-芳基丙基三氟甲磺酰胺以良好的产率提供相应的 N-三氟甲磺酰基-1,2,3,4-四氢喹啉。
• Cyclic amination onto aromatic ring of sulfonamides with (diacetoxyiodo)arenes: Effect of sulfonyl group
  作者：Hideo Togo、Yoichiro Hoshina、Masataka Yokoyama

  DOI：10.1016/0040-4039(96)01292-0

  日期：1996.8

  Sulfonamides of primary amine bearing an aromatic ring at γ-position were treated with (diacetoxyiodo)arene and iodine under irradiation conditions with a tungsten lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields. The present reaction proceeded under mild and neutral conditions.

  用（二乙酰氧基碘）芳烃和碘在钨丝灯的照射条件下，用γ-二芳氧基碘处理伯胺在γ位带有芳环的磺酰胺，以中等至良好的产率得到相应的1,2,3,4-四氢喹啉衍生物。本反应在温和和中性条件下进行。
• Cyclic Amination onto Aromatic Ring via Radical Pathway with (Diacetoxyiodo)arenes
  作者：Hideo Togo、Yoichiro Hoshina、Masataka Yokoyama

  DOI：10.1080/10426509708545592

  日期：1997.1.1

  Sulfonamides of primary amine bearing an aromatic ring at γ-position were treated with (diacetoxyiodo)arene and iodine under irradiation conditions with a tungsten lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields.

  在用钨灯照射条件下，用（二乙酰氧基碘）芳烃和碘处理γ-位带有芳环的伯胺磺酰胺，以中等至良好的产率得到相应的1,2,3,4-四氢喹啉衍生物。