7-chloro-N-(3-trimethylsilylpropyl)quinolin-4-amine | 1416711-38-0

• 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
• 英文名称: 7-chloro-N-(3-trimethylsilylpropyl)quinolin-4-amine
• CAS: 1416711-38-0
• 化学式: C₁₅H₂₁ClN₂Si
• 分子量: 292.884
• InChiKey: JPNZNDXHZYIVKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [η⁶-(2-phenoxyethanol)RuCl₂]₂ 、 7-chloro-N-(3-trimethylsilylpropyl)quinolin-4-amine 以 二氯甲烷 为溶剂， 反应 2.0h， 以61.4%的产率得到
  参考文献：
  名称：

  Synthesis, Characterization, and Pharmacological Evaluation of Silicon-Containing Aminoquinoline Organometallic Complexes As Antiplasmodial, Antitumor, and Antimycobacterial Agents

  摘要：

  Two silicon-containing analogues (1, 2) of chloroquine, modified in the lateral side chain with organosilicon moieties, were synthesized. Compounds 1 and 2 were further reacted with dinuclear half-sandwich transition metal precursors [Ru(Ar)(mu-Cl)Cl](2) (Ar = eta(6)-p-(PrC6H4Me)-Pr-i; eta(6)-C6H6; eta(6)-C6H5OCH2CH2OH), [Rh(COD)(mu-Cl)](2), and [RhCp*(mu-Cl)Cl](2), to yield a series of neutral mononuclear Ru(II), Rh(I), and Rh(III) silicon-aminoquinoline complexes (3-12). Compounds 1 and 2 act as monodentate donors that coordinate to the transition metals via the quinoline nitrogen of the aminoquinoline scaffold. All the compounds were characterized using various analytical and spectroscopic techniques, and the molecular structures of compounds 2 and 11 were elucidated by single-crystal X-ray diffraction analysis. Furthermore, the in vitro pharmacological activities of compounds 1-12 were established against chloroquine-sensitive (NF54) and chloroquine-resistant (Dd2) strains of the malarial parasite Plasmodium falciparum and against the pathogenic bacterium Mycobacterium tuberculosis H37Rv, as well as an esophageal (WHCO1) cancer cell line.

  DOI：

  10.1021/om300945c
• 作为产物：
  描述：

  4,7-二氯喹啉 、 3-氨基丙基三甲基硅烷 以 neat (no solvent) 为溶剂， 反应 6.0h， 以63%的产率得到7-chloro-N-(3-trimethylsilylpropyl)quinolin-4-amine
  参考文献：
  名称：

  Synthesis, Characterization, and Pharmacological Evaluation of Silicon-Containing Aminoquinoline Organometallic Complexes As Antiplasmodial, Antitumor, and Antimycobacterial Agents

  摘要：

  Two silicon-containing analogues (1, 2) of chloroquine, modified in the lateral side chain with organosilicon moieties, were synthesized. Compounds 1 and 2 were further reacted with dinuclear half-sandwich transition metal precursors [Ru(Ar)(mu-Cl)Cl](2) (Ar = eta(6)-p-(PrC6H4Me)-Pr-i; eta(6)-C6H6; eta(6)-C6H5OCH2CH2OH), [Rh(COD)(mu-Cl)](2), and [RhCp*(mu-Cl)Cl](2), to yield a series of neutral mononuclear Ru(II), Rh(I), and Rh(III) silicon-aminoquinoline complexes (3-12). Compounds 1 and 2 act as monodentate donors that coordinate to the transition metals via the quinoline nitrogen of the aminoquinoline scaffold. All the compounds were characterized using various analytical and spectroscopic techniques, and the molecular structures of compounds 2 and 11 were elucidated by single-crystal X-ray diffraction analysis. Furthermore, the in vitro pharmacological activities of compounds 1-12 were established against chloroquine-sensitive (NF54) and chloroquine-resistant (Dd2) strains of the malarial parasite Plasmodium falciparum and against the pathogenic bacterium Mycobacterium tuberculosis H37Rv, as well as an esophageal (WHCO1) cancer cell line.

  DOI：

  10.1021/om300945c

文献信息

• Synthesis, Characterization, and Pharmacological Evaluation of Silicon-Containing Aminoquinoline Organometallic Complexes As Antiplasmodial, Antitumor, and Antimycobacterial Agents
  作者：Yiqun Li、Carmen de Kock、Peter J. Smith、Hajira Guzgay、Denver T. Hendricks、Krupa Naran、Valerie Mizrahi、Digby F. Warner、Kelly Chibale、Gregory S. Smith

  DOI：10.1021/om300945c

  日期：2013.1.14

  Two silicon-containing analogues (1, 2) of chloroquine, modified in the lateral side chain with organosilicon moieties, were synthesized. Compounds 1 and 2 were further reacted with dinuclear half-sandwich transition metal precursors [Ru(Ar)(mu-Cl)Cl](2) (Ar = eta(6)-p-(PrC6H4Me)-Pr-i; eta(6)-C6H6; eta(6)-C6H5OCH2CH2OH), [Rh(COD)(mu-Cl)](2), and [RhCp*(mu-Cl)Cl](2), to yield a series of neutral mononuclear Ru(II), Rh(I), and Rh(III) silicon-aminoquinoline complexes (3-12). Compounds 1 and 2 act as monodentate donors that coordinate to the transition metals via the quinoline nitrogen of the aminoquinoline scaffold. All the compounds were characterized using various analytical and spectroscopic techniques, and the molecular structures of compounds 2 and 11 were elucidated by single-crystal X-ray diffraction analysis. Furthermore, the in vitro pharmacological activities of compounds 1-12 were established against chloroquine-sensitive (NF54) and chloroquine-resistant (Dd2) strains of the malarial parasite Plasmodium falciparum and against the pathogenic bacterium Mycobacterium tuberculosis H37Rv, as well as an esophageal (WHCO1) cancer cell line.