7-(4-tert-butoxycarbonylpipirazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester | 952653-63-3

• 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-tert-butoxycarbonylpipirazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 7-(4-(tert-butoxycarbonyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate；Ethyl 7-(4-(tert-butoxycarbonyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate；ethyl 1-cyclopropyl-6-fluoro-7-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylate
• CAS: 952653-63-3
• 化学式: C₂₄H₃₀FN₃O₅
• 分子量: 459.518
• InChiKey: JHEUUENQNBZTHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  610.9±55.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-(4-tert-butoxycarbonylpipirazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 在 盐酸 、 selenium(IV) oxide 、 copper(l) iodide 、 双氧水 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 ciprofloxacin
  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：

  4-[4-(3-cyclopropylamino-2-ethoxycarbonylacryloyl)-2,5-difluorophenyl]piperazine-1-carboxylic acid tert-butyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到7-(4-tert-butoxycarbonylpipirazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Identification, biological activity, and mechanism of the anti-ischemic quinolone analog

  摘要：

  The quinolone analog SQ-4004 has been identified as a potentially excellent anti-ischemic agent, which exhibited highly potent efficacy in reducing infarct volume size in vivo rat MCAO model (32.1% at 0.01 mg/kg) and potent cardioprotective effect at myocardial infarction in vivo model (26.6% at 0.01 mg/kg) while it exhibited highly reduced anti-bacterial activity. The mechanistic study revealed that the anti-ischemic activity might exert via an anti-apoptotic pathway, which implies its therapeutic uses against the ischemic cell injuries including ischemic stroke and ischemic heart disease. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.009

文献信息

• Optimizing Solubility and Permeability of a Biopharmaceutics Classification System (BCS) Class 4 Antibiotic Drug Using Lipophilic Fragments Disturbing the Crystal Lattice
  作者：Ulrika Tehler、Jonas H. Fagerberg、Richard Svensson、Mats Larhed、Per Artursson、Christel A. S. Bergström

  DOI：10.1021/jm301721e

  日期：2013.3.28

  Esterification was used to simultaneously increase solubility and permeability of ciprofloxacin, a biopharmaceutics classification system (BCS) class 4 drug (low solubility/low permeability) with solid-state limited solubility. Molecular flexibility was increased to disturb the crystal lattice, lower the melting point, and thereby improve the solubility, whereas lipophilicity was increased to enhance the intestinal permeability. These structural changes resulted in BCS class 1 analogues (high solubility/high permeability) emphasizing that simple medicinal chemistry may improve both these properties.