1-cyclopropyl-6-fluoro-7-(4-((2-(((3-methyloxetan-3-yl)methyl)sulfinyl)ethoxy)carbonyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 1616892-19-3

• 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: 1-cyclopropyl-6-fluoro-7-(4-((2-(((3-methyloxetan-3-yl)methyl)sulfinyl)ethoxy)carbonyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6-fluoro-7-[4-[2-[(3-methyloxetan-3-yl)methylsulfinyl]ethoxycarbonyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-6-fluoro-7-[4-[2-[(3-methyloxetan-3-yl)methylsulfinyl]ethoxycarbonyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 1616892-19-3
• 化学式: C₂₅H₃₀FN₃O₇S
• 分子量: 535.594
• InChiKey: GWWFCIDKNKKBIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C (decomp)
• 沸点：
  792.0±60.0 °C(predicted)
• 密度：
  1.494±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-(((3-methyloxetan-3-yl)methyl)sulfinyl)ethanol 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 1-cyclopropyl-6-fluoro-7-(4-((2-(((3-methyloxetan-3-yl)methyl)sulfinyl)ethoxy)carbonyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  An Uncharged Oxetanyl Sulfoxide as a Covalent Modifier for Improving Aqueous Solubility

  摘要：

  Low aqueous solubility is a common challenge in drug discovery and development and can lead to inconclusive biological assay results. Attaching small, polar groups that do not interfere with the bioactivity of the pharmacophore often improves solubility, but there is a dearth of viable neutral moieties available for this purpose. We have modified several poorly soluble drugs or drug candidates with the oxetanyl sulfoxide moiety of the DMSO analog MMS-350 and noted in most cases a moderate to large improvement of aqueous solubility. Furthermore, the membrane permeability of a test sample was enhanced compared to the parent compound.

  DOI：

  10.1021/ml5001504

文献信息

• An Uncharged Oxetanyl Sulfoxide as a Covalent Modifier for Improving Aqueous Solubility
  作者：Erin M. Skoda、Joshua R. Sacher、Mustafa Z. Kazancioglu、Jaideep Saha、Peter Wipf

  DOI：10.1021/ml5001504

  日期：2014.8.14

  Low aqueous solubility is a common challenge in drug discovery and development and can lead to inconclusive biological assay results. Attaching small, polar groups that do not interfere with the bioactivity of the pharmacophore often improves solubility, but there is a dearth of viable neutral moieties available for this purpose. We have modified several poorly soluble drugs or drug candidates with the oxetanyl sulfoxide moiety of the DMSO analog MMS-350 and noted in most cases a moderate to large improvement of aqueous solubility. Furthermore, the membrane permeability of a test sample was enhanced compared to the parent compound.