Tert-butyl 4-[3-bromo-1-cyclopropyl-6-fluoro-2-(hydroxymethyl)-4-oxoquinolin-7-yl]piperazine-1-carboxylate | 1421641-25-9

• 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: Tert-butyl 4-[3-bromo-1-cyclopropyl-6-fluoro-2-(hydroxymethyl)-4-oxoquinolin-7-yl]piperazine-1-carboxylate
• 英文别名: tert-butyl 4-[3-bromo-1-cyclopropyl-6-fluoro-2-(hydroxymethyl)-4-oxoquinolin-7-yl]piperazine-1-carboxylate
• CAS: 1421641-25-9
• 化学式: C₂₂H₂₇BrFN₃O₄
• 分子量: 496.376
• InChiKey: PJWIZQCIYDSUDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-[3-bromo-1-cyclopropyl-6-fluoro-2-(hydroxymethyl)-4-oxoquinolin-7-yl]piperazine-1-carboxylate 在 盐酸 、 lithium chloro-isopropyl-magnesium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.83h， 生成 4-cyclopropyl-7-fluoro-1-hydroxy-6-piperazin-1-yl-3H-oxaborolo[4,3-b]quinolin-9-one
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of a novel tricyclic oxaborole-fused fluoroquinolone

  摘要：

  We have designed and synthesized a novel class of compounds based on fluoroquinolone antibacterial prototype. The design concept involved the replacement of the 3-carboxylic acid in ciprofloxacin with an oxaborole-fused ring as an acid-mimicking group. The synthetic method employed in this work provides a good example of incorporating boron atom in complex molecules with multiple functional groups. The antibacterial activity of the newly synthesized compounds has been evaluated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.045
• 作为产物：
  描述：

  环丙沙星 在 盐酸 、 selenium(IV) oxide 、 sodium tetrahydroborate 、 copper(l) iodide 、 硫酸 、 双氧水 、 sodium hydride 、 pyridinium hydrobromide perbromide 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 47.5h， 生成 Tert-butyl 4-[3-bromo-1-cyclopropyl-6-fluoro-2-(hydroxymethyl)-4-oxoquinolin-7-yl]piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of a novel tricyclic oxaborole-fused fluoroquinolone

  摘要：

  We have designed and synthesized a novel class of compounds based on fluoroquinolone antibacterial prototype. The design concept involved the replacement of the 3-carboxylic acid in ciprofloxacin with an oxaborole-fused ring as an acid-mimicking group. The synthetic method employed in this work provides a good example of incorporating boron atom in complex molecules with multiple functional groups. The antibacterial activity of the newly synthesized compounds has been evaluated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.045

文献信息

• Synthesis and antibacterial evaluation of a novel tricyclic oxaborole-fused fluoroquinolone
  作者：Xianfeng Li、Yong-Kang Zhang、Jacob J. Plattner、Weimin Mao、M.R.K. Alley、Yi Xia、Vincent Hernandez、Yasheen Zhou、Charles Z. Ding、Jinpeng Li、Zhijun Shao、Hongwei Zhang、Musheng Xu

  DOI：10.1016/j.bmcl.2012.12.045

  日期：2013.2

  We have designed and synthesized a novel class of compounds based on fluoroquinolone antibacterial prototype. The design concept involved the replacement of the 3-carboxylic acid in ciprofloxacin with an oxaborole-fused ring as an acid-mimicking group. The synthetic method employed in this work provides a good example of incorporating boron atom in complex molecules with multiple functional groups. The antibacterial activity of the newly synthesized compounds has been evaluated. (C) 2012 Elsevier Ltd. All rights reserved.