7-(4-(3-(1H-benzo[d]imidazol-2-ylthio)-2-hydroxypropyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid | 1453858-90-6

• 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-(4-(3-(1H-benzo[d]imidazol-2-ylthio)-2-hydroxypropyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid
• 英文别名: 7-[4-[3-(1H-benzimidazol-2-ylsulfanyl)-2-hydroxypropyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
• CAS: 1453858-90-6
• 化学式: C₂₈H₃₀FN₅O₅S
• 分子量: 567.641
• InChiKey: LALOYDJCGQKTTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  7-(4-(3-(1H-benzo[d]imidazol-2-ylthio)-2-hydroxypropyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid 在 双氧水 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到7-(4-(3-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-hydroxypropyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and Antimicrobial Evaluation of Novel N-Substituted β-Hydroxy Benzimidazole Sulfone Fluoroquinolones by Selective Oxidation Using Ticl₄-H₂O₂

  摘要：

  The synthesis of N-substituted -hydroxy benzimidazole sulfones containing 8-methoxy fluoroquinolone has been described and they were evaluated for antimicrobial activities. The compounds of N-substituted -hydroxy benzimidazole sulfides (4a-e) and N-substituted -hydroxy benzimidazole sulfones (5a-e) at C-7 of fluoroquinoline exhibited superior activity in vitro. 8-Methoxy fluoroquinolone carboxylic acid (1), reaction with piperizine in acetonitrile in presence of triethylamine under reflux gives 7-piperazinyl-8-methoxyfluoroquinolone (2). The latter is reacted with epichlorohydrine in presence of NaOH in acetone yielded N-substituted epoxide (3), which on treatment with 5-substituted-2-mercaptobenzimidazoles gives N-substituted -hydroxy benzimidazole sulfides (4). Further, 4 on treatment with TiCl4-H2O2 and in DCM yielded the corresponding N-substituted -hydroxy benzimidazole sulfone (5).

  DOI：

  10.1080/10426507.2012.740702
• 作为产物：
  描述：

  1-环丙基-6,7-二氟-1,4-二氢-8-甲氧基-4-氧代-3-喹啉羧酸 在 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 10.0h， 生成 7-(4-(3-(1H-benzo[d]imidazol-2-ylthio)-2-hydroxypropyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and Antimicrobial Evaluation of Novel N-Substituted β-Hydroxy Benzimidazole Sulfone Fluoroquinolones by Selective Oxidation Using Ticl₄-H₂O₂

  摘要：

  The synthesis of N-substituted -hydroxy benzimidazole sulfones containing 8-methoxy fluoroquinolone has been described and they were evaluated for antimicrobial activities. The compounds of N-substituted -hydroxy benzimidazole sulfides (4a-e) and N-substituted -hydroxy benzimidazole sulfones (5a-e) at C-7 of fluoroquinoline exhibited superior activity in vitro. 8-Methoxy fluoroquinolone carboxylic acid (1), reaction with piperizine in acetonitrile in presence of triethylamine under reflux gives 7-piperazinyl-8-methoxyfluoroquinolone (2). The latter is reacted with epichlorohydrine in presence of NaOH in acetone yielded N-substituted epoxide (3), which on treatment with 5-substituted-2-mercaptobenzimidazoles gives N-substituted -hydroxy benzimidazole sulfides (4). Further, 4 on treatment with TiCl4-H2O2 and in DCM yielded the corresponding N-substituted -hydroxy benzimidazole sulfone (5).

  DOI：

  10.1080/10426507.2012.740702