(4R)-2-(2-((1S,2S,6R,8S)-8-((2,2-ddimethylbutanoyl)oxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)-6-oxotetrahydro-2H-pyran-4-yl 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: (4R)-2-(2-((1S,2S,6R,8S)-8-((2,2-ddimethylbutanoyl)oxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)-6-oxotetrahydro-2H-pyran-4-yl 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanoate
• 英文别名: [(2R,4R)-2-[2-[(1S,2S,6R,8S,8aR)-8-(2,2-dimethylbutanoyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-6-oxooxan-4-yl] 6-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]hexanoate
• 化学式: C₃₇H₅₀N₄O₉
• 分子量: 694.825
• InChiKey: GMJARLIANZAZRD-SPOZBLIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  176
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  4-氯-7-硝基苯并-2-氧杂-1,3-二唑 在 2,4,6-三氯苯甲酰氯 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 0.58h， 生成 (4R)-2-(2-((1S,2S,6R,8S)-8-((2,2-ddimethylbutanoyl)oxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)-6-oxotetrahydro-2H-pyran-4-yl 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanoate
  参考文献：
  名称：

  One-Pot Fluorescent Labeling Protocol for Complex Hydroxylated Bioactive Natural Products

  摘要：

  Tagging of small bioactive molecules with a fluorophore is a highly sensitive method to trace their cellular activities through real-time visual information. Here we disclose a 7-nitrobenzo-2-oxa-1,3-diazole (NBD)-based, high-yielding, one-pot labeling protocol for hydroxylated molecules using Yamaguchi coupling as the key reaction. This methodology was successfully applied on several sensitive and complex hydroxylated bioactive compounds including 7-deacetylazadiradione, simvastatin, camptothecin, andrographolide, cinchonine, beta-dihydroartemisinin, and azadirachtin A. Further, utility of this protocol was illustrated on the cytotoxic activity of azadiradione derivatives against several cancer cell lines through cell imaging of two qualified fluorescent probes.

  DOI：

  10.1021/jo401559t

文献信息

• One-Pot Fluorescent Labeling Protocol for Complex Hydroxylated Bioactive Natural Products
  作者：Saikat Haldar、Santosh Kumar、Swati P. Kolet、Harshal S. Patil、Dhiraj Kumar、Gopal C. Kundu、Hirekodathakallu V. Thulasiram

  DOI：10.1021/jo401559t

  日期：2013.10.18

  Tagging of small bioactive molecules with a fluorophore is a highly sensitive method to trace their cellular activities through real-time visual information. Here we disclose a 7-nitrobenzo-2-oxa-1,3-diazole (NBD)-based, high-yielding, one-pot labeling protocol for hydroxylated molecules using Yamaguchi coupling as the key reaction. This methodology was successfully applied on several sensitive and complex hydroxylated bioactive compounds including 7-deacetylazadiradione, simvastatin, camptothecin, andrographolide, cinchonine, beta-dihydroartemisinin, and azadirachtin A. Further, utility of this protocol was illustrated on the cytotoxic activity of azadiradione derivatives against several cancer cell lines through cell imaging of two qualified fluorescent probes.