3-碘喹啉-8-胺 | 497084-47-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 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: 3-碘喹啉-8-胺
• 中文别名: 3-碘-8-氨基喹啉
• 英文名称: 8-amino-3-iodoquinoline
• 英文别名: 3-iodoquinolin-8-amine；3-iodo-8-aminoquinoline
• CAS: 497084-47-6
• 化学式: C₉H₇IN₂
• 分子量: 270.072
• InChiKey: DXMKBPNVNXDMHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-碘喹啉-8-胺 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Effect of 3-subsitution of quinolinehydroxamic acids on selectivity of histone deacetylase isoforms

  摘要：

  A series of 3-subsituted quinolinehydroxamic acids has been synthesised and evaluated for their effect on human lung cancer cell line (A549), human colorectal cancer cell line (HCT116) and HDAC isoforms 1, 2, 6, and 8. The results indicated that substitution at C3 of quinoline is favoured for HDAC6 selectivity. Two compounds (25 and 26) were also found to be potent anti-proliferative compounds with IC50 values ranging from 1.29 to 2.13 mu M against A549 and HCT116 cells. These compounds displayed remarkable selectivity for HDAC6 over other HDAC isoforms with nanomolar IC50 values. Western blot analysis revealed that compounds of this series activate apoptotic caspase pathway as indicated by cleavage of caspase 3, 8, and 9 and also increase phosphorylated H2AX thus inducing DNA double strand fragmentation in a concentration dependent manner. Flow cytometric analysis also displayed a dose dependent increase of cell population in sub G1 phase.

  DOI：

  10.1080/14756366.2020.1839446
• 作为产物：
  描述：

  3-I碘-8-硝基喹啉 在 铁粉 作用下， 以 甲醇 为溶剂， 生成 3-碘喹啉-8-胺
  参考文献：
  名称：

  Effect of 3-subsitution of quinolinehydroxamic acids on selectivity of histone deacetylase isoforms

  摘要：

  A series of 3-subsituted quinolinehydroxamic acids has been synthesised and evaluated for their effect on human lung cancer cell line (A549), human colorectal cancer cell line (HCT116) and HDAC isoforms 1, 2, 6, and 8. The results indicated that substitution at C3 of quinoline is favoured for HDAC6 selectivity. Two compounds (25 and 26) were also found to be potent anti-proliferative compounds with IC50 values ranging from 1.29 to 2.13 mu M against A549 and HCT116 cells. These compounds displayed remarkable selectivity for HDAC6 over other HDAC isoforms with nanomolar IC50 values. Western blot analysis revealed that compounds of this series activate apoptotic caspase pathway as indicated by cleavage of caspase 3, 8, and 9 and also increase phosphorylated H2AX thus inducing DNA double strand fragmentation in a concentration dependent manner. Flow cytometric analysis also displayed a dose dependent increase of cell population in sub G1 phase.

  DOI：

  10.1080/14756366.2020.1839446

文献信息

• Site-selective C5–H and <i>N</i>–H alkylation of unprotected 8-aminoquinolines
  作者：Ozge Turbedaroglu、Ferruh Lafzi、Haydar Kilic

  DOI：10.1039/d2cc00780k

  日期：——

  We report a highly site-selective direct C5–H and N–H alkylation of free amine group-bearing 8-aminoquinolines in high to excellent yields.

  我们报道了一种高度位点选择性的直接C5-H和N-H烷基化自由胺基8-氨基喹啉的方法，产率高至极好。
• Ruthenium-Catalyzed Difluoroalkylation of 8-Aminoquinoline Amides at the C5-Position
  作者：Changpeng Chen、Runsheng Zeng、Jingyu Zhang、Yingsheng Zhao

  DOI：10.1002/ejoc.201701150

  日期：2017.12.15

  A ruthenium‐catalyzed highly selective difluoromethylation of 8‐aminoquinoline amides at the C5 position has been developed. It tolerates a broad range of functional groups, providing the corresponding difluoromethylated products in moderate to good yields. Preliminary experimental results indicate that the tricoordinate ruthenium intermediate is the key factor in achieving the C5‐position selectivity.
• Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway
  作者：Chiranjit Sen、Tapan Sahoo、Harshvardhan Singh、Eringathodi Suresh、Subhash Chandra Ghosh

  DOI：10.1021/acs.joc.9b00942

  日期：2019.8.16

  An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ^•CBr₃ radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.
• Preparation and Antifungal Activity of 3-Iodo- and 6-Iodo-8-quinolinols
  作者：Herman Gershon、Donald D. Clarke、John J. McMahon、Muriel Gershon

  DOI：10.1007/s00706-002-0495-6

  日期：2002.9.1

  3-Iodo- and 6-Iodo-8-quinolinols were prepared and tested against six fungi: Aspergillus niger, A. oryzae, Myrothecium verrucaria, Trichoderma viride, Mucor cirinelloides, and Trichopkyton mentagrophytes in Sabouraud dextrose broth. A comparison with the previously known 5-iodo- and 7-iodo-8-quinolinols showed that the 6-iodo isomer was the most active.
• Effect of 3-subsitution of quinolinehydroxamic acids on selectivity of histone deacetylase isoforms
  作者：Samir Mehndiratta、Mei-Chuan Chen、Yuh-Hsuan Chao、Cheng-Hsin Lee、Jing-Ping Liou、Mei-Jung Lai、Hsueh-Yun Lee

  DOI：10.1080/14756366.2020.1839446

  日期：2021.1.1

  A series of 3-subsituted quinolinehydroxamic acids has been synthesised and evaluated for their effect on human lung cancer cell line (A549), human colorectal cancer cell line (HCT116) and HDAC isoforms 1, 2, 6, and 8. The results indicated that substitution at C3 of quinoline is favoured for HDAC6 selectivity. Two compounds (25 and 26) were also found to be potent anti-proliferative compounds with IC50 values ranging from 1.29 to 2.13 mu M against A549 and HCT116 cells. These compounds displayed remarkable selectivity for HDAC6 over other HDAC isoforms with nanomolar IC50 values. Western blot analysis revealed that compounds of this series activate apoptotic caspase pathway as indicated by cleavage of caspase 3, 8, and 9 and also increase phosphorylated H2AX thus inducing DNA double strand fragmentation in a concentration dependent manner. Flow cytometric analysis also displayed a dose dependent increase of cell population in sub G1 phase.