N-methyl-5-nitroquinoline methanesulfonate | 236093-03-1

• 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: N-methyl-5-nitroquinoline methanesulfonate
• 英文别名: Quinolinium, 1-methyl-5-nitro-, methanesulfonate；methanesulfonate;1-methyl-5-nitroquinolin-1-ium
• CAS: 236093-03-1
• 化学式: CH₃O₃S*C₁₀H₉N₂O₂
• 分子量: 284.293
• InChiKey: GWTNLXRMKFRSSG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲磺酸甲酯 、 5-硝基喹啉 反应 24.0h， 以64%的产率得到N-methyl-5-nitroquinoline methanesulfonate
  参考文献：
  名称：

  Substituent effect of a fluorine atom on the mutagenicity of nitroquinolines

  摘要：

  Some 16 nitroquinolines (NQs) and their fluorinated derivatives were tested for mutagenicity in Salmonella typhimurium TA100 without S9 mix to investigate the effect of fluorine-substitution on the mutagenicity. These NQs consist of 5-NQs, 5-nitroquinoline N-oxides (5-NQOs), N-methyl-5-nitroquinolinium methanesulfonates (N-Me-5-NQs) and 8-NQs, including three ortho-F-NQs, one meta-F-NQ, four para-F-NQs and four 3-F-NQs. For this purpose, eight F-NQs were newly synthesized. The data indicated that the ratio of the mutagenic activities (revertants/plate/nmol) of fluorinated NQs to those of the corresponding parent non-fluorinated compounds ranged from 0.6- to 119-fold. The fluorine atom located para to the nitro group markedly enhanced the mutagenicity (24-fold and more), while three ortho-fluorinated derivatives showed no significant increase in mutagenicity (enhancement ratio were 0.6, 0.8 and 1.7). With respect to 8-NQs, its meta-fluorinated derivative also had an enhanced mutagenicity over the parent compound (53-fold). In addition, although N-Me-5-NQ was less mutagenic than 5-NQ and 5-NQO, the mutagenicity of N-Me-5-NQ was most significantly enhanced by fluorine-substitution. These results suggest that introduction of a fluorine atom to the molecule in question may be a useful tool to modify their mutagenic potency and to better understand the mechanism of mutation. (C) 1999 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1383-5718(99)00049-2

文献信息

• Substituent effect of a fluorine atom on the mutagenicity of nitroquinolines
  作者：Ken-ichi Saeki、Ryuichi Murakami、Arihiro Kohara、Naoaki Shimizu、Hiroshi Kawai、Yutaka Kawazoe、Atsushi Hakura

  DOI：10.1016/s1383-5718(99)00049-2

  日期：1999.5

  Some 16 nitroquinolines (NQs) and their fluorinated derivatives were tested for mutagenicity in Salmonella typhimurium TA100 without S9 mix to investigate the effect of fluorine-substitution on the mutagenicity. These NQs consist of 5-NQs, 5-nitroquinoline N-oxides (5-NQOs), N-methyl-5-nitroquinolinium methanesulfonates (N-Me-5-NQs) and 8-NQs, including three ortho-F-NQs, one meta-F-NQ, four para-F-NQs and four 3-F-NQs. For this purpose, eight F-NQs were newly synthesized. The data indicated that the ratio of the mutagenic activities (revertants/plate/nmol) of fluorinated NQs to those of the corresponding parent non-fluorinated compounds ranged from 0.6- to 119-fold. The fluorine atom located para to the nitro group markedly enhanced the mutagenicity (24-fold and more), while three ortho-fluorinated derivatives showed no significant increase in mutagenicity (enhancement ratio were 0.6, 0.8 and 1.7). With respect to 8-NQs, its meta-fluorinated derivative also had an enhanced mutagenicity over the parent compound (53-fold). In addition, although N-Me-5-NQ was less mutagenic than 5-NQ and 5-NQO, the mutagenicity of N-Me-5-NQ was most significantly enhanced by fluorine-substitution. These results suggest that introduction of a fluorine atom to the molecule in question may be a useful tool to modify their mutagenic potency and to better understand the mechanism of mutation. (C) 1999 Elsevier Science B.V. All rights reserved.