7-chloro-N-(trimethylsilylmethyl)quinolin-4-amine | 1416711-37-9

• 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
• 英文名称: 7-chloro-N-(trimethylsilylmethyl)quinolin-4-amine
• CAS: 1416711-37-9
• 化学式: C₁₃H₁₇ClN₂Si
• 分子量: 264.83
• InChiKey: IGZBJVHMYKHOJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-(trimethylsilylmethyl)quinolin-4-amine 以 二氯甲烷 为溶剂， 反应 2.0h， 以53.9%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 、 氨甲基三甲基硅烷 以 neat (no solvent) 为溶剂， 反应 6.0h， 以79.2%的产率得到7-chloro-N-(trimethylsilylmethyl)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
• 作为试剂：
  描述：

  hematin 在 7-chloro-N-(trimethylsilylmethyl)quinolin-4-amine 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 β-hematin
  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

• DMSO-Mediated Ligand Dissociation: Renaissance for Biological Activity of<i>N</i>-Heterocyclic-[Ru(η⁶-arene)Cl₂] Drug Candidates
  作者：Malay Patra、Tanmaya Joshi、Vanessa Pierroz、Katrin Ingram、Marcel Kaiser、Stefano Ferrari、Bernhard Spingler、Jennifer Keiser、Gilles Gasser

  DOI：10.1002/chem.201303341

  日期：2013.10.25

  spectroscopic examination revealed that [Ru(η6‐arene)Cl2(L)] (L=N‐heterocyclic ligands) complexes readily undergo a ligand exchange reaction in DMSO (see scheme), a popular medium for preparing stock solutions for biological screening. It is therefore highly important for researchers to study the stability in DMSO before reporting on the biological activity of such complexes.

  在雷达下滑倒？ 1 1 H NMR光谱检查发现的[Ru（η 6 -arene）氯2（L）]（L = N-杂环配位体）配合物容易经历在DMSO（参见方案），一个流行的介质中的配位体交换反应制备储备溶液用于生物筛选。因此，对于研究人员而言，在报道此类复合物的生物活性之前研究其在DMSO中的稳定性非常重要。