4-Azido-3-(2-chloroethyl)-6,8-dimethoxy-2-methylquinoline | 200932-42-9

• 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: 4-Azido-3-(2-chloroethyl)-6,8-dimethoxy-2-methylquinoline
• CAS: 200932-42-9
• 化学式: C₁₄H₁₅ClN₄O₂
• 分子量: 306.752
• InChiKey: PUZURBOENOZAST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Azido-3-(2-chloroethyl)-6,8-dimethoxy-2-methylquinoline 在 三苯基膦 作用下， 以 丙酮 为溶剂， 以53.3%的产率得到6,8-Dimethoxy-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline
  参考文献：
  名称：

  Potential antineoplastics. Synthesis and cytotoxicity of certain 4-chloro-3-(2-chloroethyl)-2-methylquinolines and related derivatives

  摘要：

  In an extension of our work in the field of nitrogen heterocycles with potential cytotoxic activity, the synthesis of some substituted 4-chloro-3-(2-chloroethyl)-2-methylquinolines (10-13) from their parent 3-[1-(phenylamino)ethylidene]-dihydro-2(3H)furanones (6-9) is reported. The conversion of 10-13 to some thieno-, furo- and pyrrolo[3,2-c]quinolines (14-27, 31-33) is also described. The compounds were evaluated for their toxicity in brine shrimp (Artemia salina), and their cytotoxicity against some clinically isolated human tumors in vitro. Several compounds exhibited good toxic activity against Artemia salina, while the furanone (6, NSC 680781) displayed good antineoplastic activity and high selectivity against some cell lines from leukemia, lung cancer, colon and melanoma panels. This compound has been selected by the NCI for further testing in a new in vivo anticancer hollow fiber assay.

  DOI：

  10.1016/s0223-5234(99)80067-1
• 作为产物：
  描述：

  4-chloro-3-(2-chloroethyl)-6,8-dimethoxy-2-methylquinoline 在 sodium azide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以80%的产率得到4-Azido-3-(2-chloroethyl)-6,8-dimethoxy-2-methylquinoline
  参考文献：
  名称：

  Potential antineoplastics. Synthesis and cytotoxicity of certain 4-chloro-3-(2-chloroethyl)-2-methylquinolines and related derivatives

  摘要：

  In an extension of our work in the field of nitrogen heterocycles with potential cytotoxic activity, the synthesis of some substituted 4-chloro-3-(2-chloroethyl)-2-methylquinolines (10-13) from their parent 3-[1-(phenylamino)ethylidene]-dihydro-2(3H)furanones (6-9) is reported. The conversion of 10-13 to some thieno-, furo- and pyrrolo[3,2-c]quinolines (14-27, 31-33) is also described. The compounds were evaluated for their toxicity in brine shrimp (Artemia salina), and their cytotoxicity against some clinically isolated human tumors in vitro. Several compounds exhibited good toxic activity against Artemia salina, while the furanone (6, NSC 680781) displayed good antineoplastic activity and high selectivity against some cell lines from leukemia, lung cancer, colon and melanoma panels. This compound has been selected by the NCI for further testing in a new in vivo anticancer hollow fiber assay.

  DOI：

  10.1016/s0223-5234(99)80067-1

文献信息

• Potential antineoplastics. Synthesis and cytotoxicity of certain 4-chloro-3-(2-chloroethyl)-2-methylquinolines and related derivatives
  作者：E-Sam Badawey、T Kappe

  DOI：10.1016/s0223-5234(99)80067-1

  日期：1997.10

  In an extension of our work in the field of nitrogen heterocycles with potential cytotoxic activity, the synthesis of some substituted 4-chloro-3-(2-chloroethyl)-2-methylquinolines (10-13) from their parent 3-[1-(phenylamino)ethylidene]-dihydro-2(3H)furanones (6-9) is reported. The conversion of 10-13 to some thieno-, furo- and pyrrolo[3,2-c]quinolines (14-27, 31-33) is also described. The compounds were evaluated for their toxicity in brine shrimp (Artemia salina), and their cytotoxicity against some clinically isolated human tumors in vitro. Several compounds exhibited good toxic activity against Artemia salina, while the furanone (6, NSC 680781) displayed good antineoplastic activity and high selectivity against some cell lines from leukemia, lung cancer, colon and melanoma panels. This compound has been selected by the NCI for further testing in a new in vivo anticancer hollow fiber assay.