(6-甲氧基-2-甲基喹啉-4-基)肼盐酸盐 | 1171611-95-2

• 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: (6-甲氧基-2-甲基喹啉-4-基)肼盐酸盐
• 英文名称: 4-hydrazino-6-methoxy-2-methylquinoline hydrochloride
• 英文别名: (6-methoxy-2-methylquinolin-4-yl)hydrazine;hydrochloride
• CAS: 1171611-95-2
• 化学式: C₁₁H₁₃N₃O*ClH
• 分子量: 239.705
• InChiKey: HNGXRBUDVCLNOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6-甲氧基-2-甲基喹啉-4-基)肼盐酸盐 在 水 作用下， 以97%的产率得到4-肼基-6-甲氧基-2-甲基喹啉
  参考文献：
  名称：

  Synthesis and some transformations of 6(8)-substituted 4-hydrazino-2-methylquinolines

  摘要：

  6(8)-Substituted 4-hydrazino-2-methylquinolines were synthesized by reaction of the corresponding 4-chloro-2-methylquinolines with hydrazine hydrate. Reactions of the title compounds with ethyl acetoacetate and acetone gave 2,4-dimethyl-1H-pyrrolo[3,2-c]quinolines and 4-(5-ethoxy-3-methyl-1H-pyrazol-1-yl)-2-methylquinolines.

  DOI：

  10.1134/s107042801003022x
• 作为产物：
  描述：

  4-氯-6-甲氧基-2-甲基喹啉 在 一水合肼 作用下， 以 乙醇 为溶剂， 以75%的产率得到(6-甲氧基-2-甲基喹啉-4-基)肼盐酸盐
  参考文献：
  名称：

  Potent DNA-directed alkylating agents: Synthesis and biological activity of phenyl N-mustard–quinoline conjugates having a urea or hydrazinecarboxamide linker

  摘要：

  A series of N-mustard-quinoline conjugates bearing a urea or hydrazinecarboxamide linker was synthesized for antitumor evaluation. The in vitro cytotoxicity studies revealed that compounds with hydrazinecarboxamide linkers were generally more cytotoxic than the corresponding urea counterparts in inhibiting human lymphoblastic leukemia and various solid tumor cell growths in culture. The therapeutic efficacy against human tumor xenografts in animal model was studied. It was shown that complete tumor remission in nude mice bearing human breast carcinoma MX-1 xenograft by 17a, i and 18c, d was achieved. In the present study, it was revealed that both linkers are able to lower the chemically reactive N-mustard pharmacophore and thus the newly synthesized conjugates possess a long half-life in rat plasma. Moreover, the new N-mustard derivatives are able to induce DNA cross-linking either by modified comet assay or by alkaline agarose gel shift assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.061

文献信息

• Potent DNA-directed alkylating agents: Synthesis and biological activity of phenyl N-mustard–quinoline conjugates having a urea or hydrazinecarboxamide linker
  作者：Rajesh Kakadiya、Huajin Dong、Amit Kumar、Dodia Narsinh、Xiuguo Zhang、Ting-Chao Chou、Te-Chang Lee、Anamik Shah、Tsann-Long Su

  DOI：10.1016/j.bmc.2010.01.061

  日期：2010.3

  A series of N-mustard-quinoline conjugates bearing a urea or hydrazinecarboxamide linker was synthesized for antitumor evaluation. The in vitro cytotoxicity studies revealed that compounds with hydrazinecarboxamide linkers were generally more cytotoxic than the corresponding urea counterparts in inhibiting human lymphoblastic leukemia and various solid tumor cell growths in culture. The therapeutic efficacy against human tumor xenografts in animal model was studied. It was shown that complete tumor remission in nude mice bearing human breast carcinoma MX-1 xenograft by 17a, i and 18c, d was achieved. In the present study, it was revealed that both linkers are able to lower the chemically reactive N-mustard pharmacophore and thus the newly synthesized conjugates possess a long half-life in rat plasma. Moreover, the new N-mustard derivatives are able to induce DNA cross-linking either by modified comet assay or by alkaline agarose gel shift assay. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and some transformations of 6(8)-substituted 4-hydrazino-2-methylquinolines
  作者：A. A. Avetisyan、I. L. Aleksanyan、L. P. Ambartsumyan

  DOI：10.1134/s107042801003022x

  日期：2010.3

  6(8)-Substituted 4-hydrazino-2-methylquinolines were synthesized by reaction of the corresponding 4-chloro-2-methylquinolines with hydrazine hydrate. Reactions of the title compounds with ethyl acetoacetate and acetone gave 2,4-dimethyl-1H-pyrrolo[3,2-c]quinolines and 4-(5-ethoxy-3-methyl-1H-pyrazol-1-yl)-2-methylquinolines.