4-[(氰基甲基)氨基]-苯甲酸乙酯 | 22433-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(氰基甲基)氨基]-苯甲酸乙酯
• 英文名称: -acetonitril
• 英文别名: p-Cyanomethylaminobenzoesaeureethylester；p-Carbethoxyanilinoacetonitril；[p-(Ethoxycarbonyl)-anilino]-acetonitril；Ethyl 4-(cyanomethylamino)benzoate
• CAS: 22433-08-5
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD16171449
• 分子量: 204.228
• InChiKey: MZLDXEMKLYQPIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  4-[(氰基甲基)氨基]-苯甲酸乙酯 在 sodium hydroxide 作用下， 生成 4-(carbamoylmethyl-amino)-benzoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of an isomer of pteroic acid, 4-[(2-amino-4-hydroxyprimido[5,4-d]pyrimidin-6-ylmethyl)amino]benzoic acid

  摘要：

  DOI：

  10.1021/jo00827a036
• 作为产物：
  描述：

  苯佐卡因 生成 4-[(氰基甲基)氨基]-苯甲酸乙酯
  参考文献：
  名称：

  Synthesis of an isomer of pteroic acid, 4-[(2-amino-4-hydroxyprimido[5,4-d]pyrimidin-6-ylmethyl)amino]benzoic acid

  摘要：

  DOI：

  10.1021/jo00827a036

文献信息

• Fluorogenic sydnonimine probes for orthogonal labeling
  作者：Wenyuan Xu、Zhuzhou Shao、Cheng Tang、Chun Zhang、Yinghan Chen、Yong Liang

  DOI：10.1039/d2ob00159d

  日期：——

  A FRET-based fluorescence turn-on probe is designed, which employs a sydnonimine as the linker to match specific fluorophore and quencher pairs and releases the fluorescence after the “click-and-release” reaction. Furthermore, we realized selective fluorescence labeling by exploiting the mutual orthogonality between sydnonimine–DIBAC and tetrazine–1,3-Cp cycloaddition pairs.

  设计了一种基于 FRET 的荧光开启探针，它采用 sydnonimine 作为连接子来匹配特定的荧光基团和猝灭剂对，并在“点击释放”反应后释放荧光。此外，我们通过利用 sydnonimine-DIBAC 和四嗪-1,3-Cp 环加成对之间的相互正交性实现了选择性荧光标记。
• Bioorthogonal “Click and Release” Reaction‐Triggered Aggregation of Gold Nanoparticles Combined with Released Lonidamine for Enhanced Cancer Photothermal Therapy
  作者：Xiao Yan、Ke Li、Tian‐Qiu Xie、Xiao‐Kang Jin、Cheng Zhang、Qian‐Ru Li、Jun Feng、Chuan‐Jun Liu、Xian‐Zheng Zhang

  DOI：10.1002/anie.202318539

  日期：2024.3.22

  Cancer has been the most deadly disease, and 13 million cancer casualties are estimated to occur each year by 2030. Gold nanoparticles (AuNPs)‐based photothermal therapy (PTT) has attracted great interest due to its high spatiotemporal controllability and noninvasiveness. Due to the trade‐off between particle size and photothermal efficiency of AuNPs, rational design is needed to realize aggregation of AuNPs into larger particles with desirable NIR adsorption in tumor site. Exploiting the bioorthogonal “Click and Release” (BCR) reaction between iminosydnone and cycloalkyne, aggregation of AuNPs can be achieved and attractively accompanied by the release of chemotherapeutic drug purposed to photothermal synergizing. We synthesize iminosydnone‐lonidamine (ImLND) as a prodrug and choose dibenzocyclooctyne (DBCO) as the trigger of BCR reaction. A PEGylated AuNPs‐based two‐component nanoplatform consisting of prodrug‐loaded AuNPs‐ImLND and tumor‐targeting peptide RGD‐conjugated AuNPs‐DBCO‐RGD is designed. In the therapeutic regimen, AuNPs‐DBCO‐RGD are intravenously injected first for tumor‐specific enrichment and retention. Once the arrival of AuNPs‐ImLND injected later at tumor site, highly photothermally active nanoaggregates of AuNPs are formed via the BCR reaction between ImLND and DBCO. The simultaneous release of lonidamine further enhanced the therapeutic performance by sensitizing cancer cells to PTT.
• Synthesis of an isomer of pteroic acid, 4-[(2-amino-4-hydroxyprimido[5,4-d]pyrimidin-6-ylmethyl)amino]benzoic acid
  作者：Dong Han Kim、Robert L. McKee

  DOI：10.1021/jo00827a036

  日期：1970.2