[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(4-iodo-2,5-dimethoxyphenyl)prop-2-ynoxy]oxan-2-yl]methyl acetate | 1609475-77-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(4-iodo-2,5-dimethoxyphenyl)prop-2-ynoxy]oxan-2-yl]methyl acetate
• CAS: 1609475-77-5
• 化学式: C₂₅H₂₉IO₁₂
• 分子量: 648.403
• InChiKey: JKLATWYGMKBTRM-NHTNDUFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(4-iodo-2,5-dimethoxyphenyl)prop-2-ynoxy]oxan-2-yl]methyl acetate 在 四(三苯基膦)钯 、 三乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-[4-[4-[2,5-dimethoxy-4-[3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyprop-1-ynyl]phenyl]buta-1,3-diynyl]-2,5-dimethoxyphenyl]prop-2-ynoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Oligo(phenylene ethynylene) Glucosides: Modulation of Cellular Uptake Capacity Preserving Light ON

  摘要：

  A new family of oligo(phenylene ethynylene) (OPE) glucosides has been prepared and characterized. Our results demonstrate that fine-tuning of their photophysical properties can be obtained by acting on the electronics of the core and molecular skeleton. Modulation of the hydrophobic chain length and substituents on the central moieties influences the bioaffinity too. In particular, introducing a NMe2 group on the aromatic central core affords a highly efficient biocompatible fluorescent probe that can be taken up in cytoplasmic vesicles of HEp-2 cells (cells from epidermoid carcinoma larynx tissue). The photophysical behavior, high quantum yield, and stability open the way to the use of the OPE family as stains for cellular imaging analysis by fluorescence microscopy.

  DOI：

  10.1021/jo500661u
• 作为产物：
  描述：

  1,4-二碘-2,5-二甲氧基苯 、 2-炔丙基-四-O-乙酰基-β-D-吡喃葡萄糖苷 在 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(4-iodo-2,5-dimethoxyphenyl)prop-2-ynoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  通过亚磺酸合成氨基官能化两亲分子的双位点反应平台

  摘要：

  描述了一些bolaamphiphiles的合成。这是一种聚合方法，允许将葡糖基衍生物连接到双功能化平台，通过无铜 Sonogashira 交叉耦合。中心核由适当取代的双亚砜与二乙炔基苯的反应获得。这种反应的中间体是容易加到不饱和分子的一个三键上的亚磺基官能团。通过将氨或哌啶亲核加成到分子骨架中已经存在的两个乙烯基磺酰基上，中心核心的功能化为制备更复杂的衍生物开辟了道路。初步理论计算证明并支持了观察到具有意想不到的显着高非对映选择性的新立体碳的形成。两个末端葡糖基部分被有利地去保护以提供氨基官能化的双亲分子。

  DOI：

  10.1039/d2ob01266a

文献信息

• Glucose-functionalized amino-OPEs as biocompatible photosensitizers in PDT
  作者：Elisa Deni、Alicia Zamarrón、Paola Bonaccorsi、M. Carmen Carreño、Ángeles Juarranz、Fausto Puntoriero、Maria Teresa Sciortino、María Ribagorda、Anna Barattucci

  DOI：10.1016/j.ejmech.2016.01.041

  日期：2016.3

  Photodynamic therapy (PDT) is a minimally invasive procedure that can provide a selective eradication of neoplastic diseases by the combined effect of a photosensitizer, light and oxygen. New amino oligo(phenylene-ethynylene)s (OPEs), bearing hydrophilic glucoside terminations, have been prepared, characterized and tested as photosensitizers in PDT. The effectiveness of these compounds in combination with UVA light has been checked on two tumor cell lines (HEp-2 and HeLa cells, derived from a larynx carcinoma and a cervical carcinoma, respectively). The compounds triggered a mitotic blockage that led to the cell death, being the effect active up to 3 mu m concentration. The photophysical properties of OPEs, such as high quantum yield, stability, singlet oxygen production, biocompatibility, easy cell internalization and very good response even at low concentration, make them promising photosensitizers in the application of PDT. (C) 2016 Elsevier Masson SAS. All rights reserved.