2-(3-methoxypropyl)-6-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3-methoxypropyl)-6-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-(3-methoxypropyl)-6-nitrobenzo[de]isoquinoline-1,3-dione
• 化学式: C₁₆H₁₄N₂O₅
• 分子量: 314.298
• InChiKey: XRSFXXKSPNOGOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-methoxypropyl)-6-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以87%的产率得到6-amino-2-(3-methoxypropyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Incorporation of fluorophore–cholesterol conjugates into liposomal and mycobacterial membranes

  摘要：

  Fluorescently-labeled steroids that emit intense blue light in nonpolar solvent (lambda(em) (CH2Cl2) approximate to 440 nm, Phi(F) = 0.70) were prepared by treating cholesteryl chloroformate with 4-amino-1,8-naphthalimides. The lipid portion of the conjugates embeds into liposomal membrane bilayers in minutes, leaving the fluorophore exposed to the external aqueous environment. This causes a 40-nm red-shift in lambda(em) and significant quenching. DFT optimizations predict the conjugates to be about 30 angstrom long when fully extended, but rotation about the linker group can bring the compounds into an 'L'-shape. Such a conformation would allow the cholesteryl anchor to remain parallel to the acyl chains of a membrane while the fluorescent group resides in the interfacial region, instead of extending beyond it. When incubated with Mycobacterium smegmatis mc2 155, a bacterial species known to use natural cholesterol, the labeled steroids support growth and can be found localized in the membrane fraction of the cells using HPLC. These findings demonstrate stable integration of fluorescent cholesterols into bacterial membranes in vivo, indicating that these compounds may be useful for evaluating cholesterol uptake in prokaryotic organisms. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.01.030