3-(2,6-bis(ethoxycarbonyl)-4,4-difluoro-1,3,5,7-tetramethyl-3a,4a-diaza-4-bora-s-indacen-8-yl)-4-methoxyphenyl azide | 1617498-64-2

• 英文名称: 3-(2,6-bis(ethoxycarbonyl)-4,4-difluoro-1,3,5,7-tetramethyl-3a,4a-diaza-4-bora-s-indacen-8-yl)-4-methoxyphenyl azide
• 英文别名: 8-(5-azido-2-methoxyphenyl)-2,6-diethoxycarbonyl-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene；8-(5-azido-2-methoxyphenyl)-2,6-diethoxycarbonyl-4,4-difluoro-1,3,5,7-tetraethyl-4-bora-3a,4a-diaza-s-indacene；AzBOCEt
• CAS: 1617498-64-2
• 化学式: C₂₆H₂₈BF₂N₅O₅
• 分子量: 539.347
• InChiKey: SHWJNAXQBIRMAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  4-戊炔-1-醇 、 3-(2,6-bis(ethoxycarbonyl)-4,4-difluoro-1,3,5,7-tetramethyl-3a,4a-diaza-4-bora-s-indacen-8-yl)-4-methoxyphenyl azide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 以90%的产率得到2,6-diethoxycarbonyl-4,4-difluoro-8-{3-[4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl]-2-methoxyphenyl}-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  An Azido-BODIPY Probe for Glycosylation: Initiation of Strong Fluorescence upon Triazole Formation

  摘要：

  We have designed a low fluorescent azido-BODIPY-based probe AzBOCEt (Az10) that undergoes copper(I)-catalyzed 1,3-dipolar cycloadditions with alkynes to yield strongly fluorescent triazole derivatives. The fluorescent quantum yield of a triazole product T10 is enhanced by 52-fold as compared to AzBOCEt upon excitation at a wavelength above SOO nm. Quantum mechanical calculations indicate that the increase in fluorescence upon triazole formation is due to the lowering of the HOMO energy level of the aryl moiety to reduce the process of acceptor photoinduced electron transfer. AzBOCEt is shown to label alkyne-functionalized proteins in vitro and glycoproteins in cells with excellent selectivity, and enables cell imaging and visualization of glycoconjugates in alkynyl-saccharide-treated cells at extremely low concentration (0.1 mu M). Furthermore, the alkyne-tagged glycoproteins from cell lysates can be directly detected with AzBOCEt in gel electrophoresis.

  DOI：

  10.1021/ja5010174
• 作为产物：
  描述：

  8-(5-amino-2-methoxyphenyl)-2,6-diethoxycarbonyl-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 在 triflic azide 、 copper(II) sulfate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 3-(2,6-bis(ethoxycarbonyl)-4,4-difluoro-1,3,5,7-tetramethyl-3a,4a-diaza-4-bora-s-indacen-8-yl)-4-methoxyphenyl azide
  参考文献：
  名称：

  An Azido-BODIPY Probe for Glycosylation: Initiation of Strong Fluorescence upon Triazole Formation

  摘要：

  We have designed a low fluorescent azido-BODIPY-based probe AzBOCEt (Az10) that undergoes copper(I)-catalyzed 1,3-dipolar cycloadditions with alkynes to yield strongly fluorescent triazole derivatives. The fluorescent quantum yield of a triazole product T10 is enhanced by 52-fold as compared to AzBOCEt upon excitation at a wavelength above SOO nm. Quantum mechanical calculations indicate that the increase in fluorescence upon triazole formation is due to the lowering of the HOMO energy level of the aryl moiety to reduce the process of acceptor photoinduced electron transfer. AzBOCEt is shown to label alkyne-functionalized proteins in vitro and glycoproteins in cells with excellent selectivity, and enables cell imaging and visualization of glycoconjugates in alkynyl-saccharide-treated cells at extremely low concentration (0.1 mu M). Furthermore, the alkyne-tagged glycoproteins from cell lysates can be directly detected with AzBOCEt in gel electrophoresis.

  DOI：

  10.1021/ja5010174

文献信息

• A facile preparation of functional cycloalkynes <i>via</i> an azide-to-cycloalkyne switching approach
  作者：Suguru Yoshida、Tomoko Kuribara、Harumi Ito、Tomohiro Meguro、Yoshitake Nishiyama、Fumika Karaki、Yasutomo Hatakeyama、Yuka Koike、Isao Kii、Takamitsu Hosoya

  DOI：10.1039/c9cc01113g

  日期：——

  incorporated with a cycloalkyne moiety, from the corresponding azides is developed. Treatment of diynes bearing strained and terminal alkyne moieties with a copper salt enabled terminal alkyne-selective click conjugation with azides, whereas a more azidophilic strained alkyne moiety was transiently protected from the click reaction via complexation with copper.

  开发了一种从相应的叠氮化物制备各种功能性环炔烃的简便方法，包括与环炔烃部分结合的蛋白质。用铜盐处理带有应变和末端炔烃部分的二炔，可实现叠氮化物对末端炔烃的选择性点击共轭作用，而通过与铜的络合，暂时保护了更多具有亲氮性的应变炔烃部分，使其免受点击反应的影响。
• Synthesis, distribution analysis and mechanism studies of N-acyl glucosamine-bearing oleanolic saponins
  作者：Yu-Pu Juang、You-Yu Lin、She-Hung Chan、Chun-Kai Chang、Jiun-Jie Shie、Yves S.Y. Hsieh、Jih-Hwa Guh、Pi-Hui Liang

  DOI：10.1016/j.bioorg.2020.103835

  日期：2020.6

  A series of N-acyl glucosamine-bearing triterpenoid saponins has been synthesized with cytotoxic activities evaluated against HL-60, PC-3, HCT-116, and CT-26 tumor cells. Saponins incorporated an oleanolic acid (OA) triterpenoidal core exhibited the highest cytotoxic activity. To study the influence of the lengths of acyl-carbon chain on N-position of glucosamine, cells were treated with 28-propargylamides and then reacted with an azidofluorogenic probe under CuAAC click reactions to visualize the intact distributions of these compounds by confocal microscopy and flow cytometry; it was found that cytotoxic-active compounds (30-32) located in the cytosol and inactive compounds bearing longer carbon chains (33-35) were impenetrable across cell membranes. Our study demonstrated the defined lipophilic acyl-carbon chain length can precisely regulate the cytotoxic activity of saponins, which is useful for the future development of cytotoxic agents. Furthermore, using quantitative proteomics and immunolabeling, the mechanism of cytotoxicity induced by the synthetic saponin after membrane penetration could be a result of activation of death receptor pathway and inhibition of PI3K/Akt/mTOR pathway.