6-(2-azidoethoxy)-3-(bromomethyl)-2-chloroquinoline | 1453254-74-4

• 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: 6-(2-azidoethoxy)-3-(bromomethyl)-2-chloroquinoline
• CAS: 1453254-74-4
• 化学式: C₁₂H₁₀BrClN₄O
• 分子量: 341.595
• InChiKey: FHDODEFNKADBSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.88
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-(2-azidoethoxy)-3-(bromomethyl)-2-chloroquinoline 在 bis(triphenylphosphine) palladium (Il) acetate 、 potassium tert-butylate 、 氢气 、 potassium acetate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 57.5h， 生成 N-[2-[[(19S)-19-ethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-7-yl]oxy]ethyl]-1-[2-(3-hydroxy-6-oxoxanthen-9-yl)benzoyl]piperidine-4-carboxamide
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and in Vivo Imaging of the first Camptothecin–Fluorescein Conjugate

  摘要：

  The first synthesis and photophysical properties of a fluorecently labeled camptothecin derivative, namely, camptothecin-FI (CPT-FI), an antitumoral agent that targets topoisomerase I, are reported. The preparation of this fluorescent conjugate is based on a highly convergent and flexible approach which enables the rapid chemical modification of the AB ring system of this fragile pentacyclic alkaloid, aimed at introducing an anchoring point to graft the fluorophore. The selection of a fluorescein analogue as the reporter group has enabled us to get the first green-emitting CPT conjugate exhibiting valuable spectral properties and retaining biological properties of native CPT. Indeed, in biological models, i.e., glioma cell lines U87 and/or T98, the kinetics of cell endocytosis, as well as the efficacy of CPT-FI were compared to those of CPT. CPT-FI fluorescence was measured in the cytosolic compartment of T98 glioma cells from 5 min treatment and remained detectable until 48 h. As CPT, CPT-FI drastically inhibited glioma growth and cell cycle but exhibited a reduced affinity as compared to the native CPT. In vivo and ex vivo imaging studies of CPT-FI intratumoraly injected into a model of NIH-3T3 marine tumor xenografts in nude mice, showed accumulation around the injected site area, which is very promising to target tumors and follow biodistribution in vivo.

  DOI：

  10.1021/bc3005304
• 作为产物：
  描述：

  6-(2-azidoethoxy)-2-chloro-quinolin-3-carbaldehyde 在 sodium tetrahydroborate 、 三溴化磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 6-(2-azidoethoxy)-3-(bromomethyl)-2-chloroquinoline
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and in Vivo Imaging of the first Camptothecin–Fluorescein Conjugate

  摘要：

  The first synthesis and photophysical properties of a fluorecently labeled camptothecin derivative, namely, camptothecin-FI (CPT-FI), an antitumoral agent that targets topoisomerase I, are reported. The preparation of this fluorescent conjugate is based on a highly convergent and flexible approach which enables the rapid chemical modification of the AB ring system of this fragile pentacyclic alkaloid, aimed at introducing an anchoring point to graft the fluorophore. The selection of a fluorescein analogue as the reporter group has enabled us to get the first green-emitting CPT conjugate exhibiting valuable spectral properties and retaining biological properties of native CPT. Indeed, in biological models, i.e., glioma cell lines U87 and/or T98, the kinetics of cell endocytosis, as well as the efficacy of CPT-FI were compared to those of CPT. CPT-FI fluorescence was measured in the cytosolic compartment of T98 glioma cells from 5 min treatment and remained detectable until 48 h. As CPT, CPT-FI drastically inhibited glioma growth and cell cycle but exhibited a reduced affinity as compared to the native CPT. In vivo and ex vivo imaging studies of CPT-FI intratumoraly injected into a model of NIH-3T3 marine tumor xenografts in nude mice, showed accumulation around the injected site area, which is very promising to target tumors and follow biodistribution in vivo.

  DOI：

  10.1021/bc3005304