Tert-butyl 2-(4-acetyl-2-methoxy-5-nitrophenoxy)acetate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Tert-butyl 2-(4-acetyl-2-methoxy-5-nitrophenoxy)acetate
• 英文别名: tert-butyl 2-(4-acetyl-2-methoxy-5-nitrophenoxy)acetate
• 化学式: C₁₅H₁₉NO₇
• 分子量: 325.318
• InChiKey: MOLIOMFFVDNCPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-(4-acetyl-2-methoxy-5-nitrophenoxy)acetate 在 甲醇 、 sodium tetrahydroborate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-(2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}ethyl)-2-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]acetamide
  参考文献：
  名称：

  Photoactivatable Prodrug of Doxazolidine Targeting Exosomes

  摘要：

  Natural lipid nanocarriers, exosomes, carry cell-signaling materials such as DNA and RNA for intercellular communications. Exosomes derived from cancer cells contribute to the progression and metastasis of cancer cells by transferring oncogenic signaling molecules to neighboring and remote premetastatic sites. Therefore, applying the unique properties of exosomes for cancer therapy has been expected in science, medicine, and drug discovery fields. Herein, we report that an exosome-targeting prodrug system, designated MARCKS-ED-photodoxaz, could spatiotemporally control the activation of an exquisitely cytotoxic agent, doxazolidine (doxaz), with UV light. The MARCKS-ED peptide enters a cell by forming a complex with the exosomes in situ at its plasma membrane and in the media. MARCKS-ED-photodoxaz releases doxaz under near-UV irradiation to inhibit cell growth with low nanomolar IC50 values. The MARCKS-ED-photodoxaz system targeting exosomes and utilizing photochemistry will potentially provide a new approach for the treatment of cancer, especially for highly progressive and invasive metastatic cancers.

  DOI：

  10.1021/acs.jmedchem.8b01508
• 作为产物：
  描述：

  tert-butyl 2-(4-acetyl-2-methoxyphenoxy)acetate 在 硝酸 、 乙酸酐 作用下， 以65%的产率得到Tert-butyl 2-(4-acetyl-2-methoxy-5-nitrophenoxy)acetate
  参考文献：
  名称：

  Photoactivatable Prodrug of Doxazolidine Targeting Exosomes

  摘要：

  Natural lipid nanocarriers, exosomes, carry cell-signaling materials such as DNA and RNA for intercellular communications. Exosomes derived from cancer cells contribute to the progression and metastasis of cancer cells by transferring oncogenic signaling molecules to neighboring and remote premetastatic sites. Therefore, applying the unique properties of exosomes for cancer therapy has been expected in science, medicine, and drug discovery fields. Herein, we report that an exosome-targeting prodrug system, designated MARCKS-ED-photodoxaz, could spatiotemporally control the activation of an exquisitely cytotoxic agent, doxazolidine (doxaz), with UV light. The MARCKS-ED peptide enters a cell by forming a complex with the exosomes in situ at its plasma membrane and in the media. MARCKS-ED-photodoxaz releases doxaz under near-UV irradiation to inhibit cell growth with low nanomolar IC50 values. The MARCKS-ED-photodoxaz system targeting exosomes and utilizing photochemistry will potentially provide a new approach for the treatment of cancer, especially for highly progressive and invasive metastatic cancers.

  DOI：

  10.1021/acs.jmedchem.8b01508

文献信息

• [EN] PHOTOCLEAVABLE DRUG CONJUGATES<br/>[FR] CONJUGUÉS DE MÉDICAMENT PHOTOCLIVABLES
  申请人：UNIV MISSOURI

  公开号：WO2014004278A1

  公开（公告）日：2014-01-03

  Novel photocleavable drug conjugates for forming drug depots comprise drugs attached to photocleavable groups. In one embodiment, the drug is linked via photocleavable group(s) to a polymer chain to form a photocleavable drug-polymer conjugate that generally forms the depot matrix. In another embodiment, the drug is crosslinked via photocleavable group(s) to themselves to form a photocleavable drug conjugate that generally forms the depot.

  新型光解药物结合物用于形成药物库，包括将药物连接到光解基团。在一个实施例中，药物通过光解基团连接到聚合物链，形成光解药物-聚合物结合物，通常形成库基质。在另一个实施例中，药物通过光解基团交联到自身，形成光解药物结合物，通常形成库。
• PHOTOCLEAVABLE DRUG CONJUGATES
  申请人：THE CURATORS OF THE UNIVERSITY OF MISSOURI

  公开号：US20150328314A1

  公开（公告）日：2015-11-19

  Novel photocleavable drug conjugates for forming drug depots comprise drugs attached to photocleavable groups. In one embodiment, the drug is linked via photocleavable group(s) to a polymer chain to form a photocleavable drug-polymer conjugate that generally forms the depot matrix. In another embodiment, the drug is crosslinked via photocleavable group(s) to themselves to form a photocleavable drug conjugate that generally forms the depot.
• Photoactivatable Prodrug of Doxazolidine Targeting Exosomes
  作者：Ryo Tamura、Alla Balabanova、Samuel A. Frakes、Austin Bargmann、Jan Grimm、Tad H. Koch、Hang Yin

  DOI：10.1021/acs.jmedchem.8b01508

  日期：2019.2.28

  Natural lipid nanocarriers, exosomes, carry cell-signaling materials such as DNA and RNA for intercellular communications. Exosomes derived from cancer cells contribute to the progression and metastasis of cancer cells by transferring oncogenic signaling molecules to neighboring and remote premetastatic sites. Therefore, applying the unique properties of exosomes for cancer therapy has been expected in science, medicine, and drug discovery fields. Herein, we report that an exosome-targeting prodrug system, designated MARCKS-ED-photodoxaz, could spatiotemporally control the activation of an exquisitely cytotoxic agent, doxazolidine (doxaz), with UV light. The MARCKS-ED peptide enters a cell by forming a complex with the exosomes in situ at its plasma membrane and in the media. MARCKS-ED-photodoxaz releases doxaz under near-UV irradiation to inhibit cell growth with low nanomolar IC50 values. The MARCKS-ED-photodoxaz system targeting exosomes and utilizing photochemistry will potentially provide a new approach for the treatment of cancer, especially for highly progressive and invasive metastatic cancers.