2-(4-acetyl-2-methoxy-5-nitro-phenoxy)-N-(2-{2-[2-(2-azido-ethoxy)ethoxy]ethoxy}ethyl)acetamide | 1425485-68-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-acetyl-2-methoxy-5-nitro-phenoxy)-N-(2-{2-[2-(2-azido-ethoxy)ethoxy]ethoxy}ethyl)acetamide
• 英文别名: AP-DMNPE amide；2-(4-acetyl-2-methoxy-5-nitrophenoxy)-N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl]acetamide
• CAS: 1425485-68-2
• 化学式: C₁₉H₂₇N₅O₉
• 分子量: 469.451
• InChiKey: SKQJUNINLWZYBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  33
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(4-acetyl-2-methoxy-5-nitro-phenoxy)-N-(2-{2-[2-(2-azido-ethoxy)ethoxy]ethoxy}ethyl)acetamide 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 copper(ll) sulfate pentahydrate 、 1-羟基苯并三唑 、 sodium ascorbate 、 三乙胺 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 水 、 叔丁醇 为溶剂， 反应 67.25h， 生成 3-[1-[2-[2-[2-[2-[[2-[4-[1-[(3aS,4S,6R,7aS)-4-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-2,3a,4,6,7,7a-hexahydropyrano[4,3-d][1,3]oxazole-1-carbonyl]oxyethyl]-2-methoxy-5-nitrophenoxy]acetyl]amino]ethoxy]ethoxy]ethoxy]ethyl]triazol-4-yl]propanoic acid
  参考文献：
  名称：

  [EN] ANTHRACYCLINE PRODRUGS AND METHODS OF MAKING AND USING THE SAME
  [FR] PROMÉDICAMENTS D'ANTHRACYNE ET PROCÉDÉS DE PRODUCTION ET D'UTILISATION DE CES DERNIERS

  摘要：

  用于预防和治疗癌症的具有治疗效果的前药化合物，以及含有这些化合物的药物组合物，以及制备和使用这些化合物的方法。

  公开号：

  WO2016176332A1
• 作为产物：
  描述：

  tert-butyl 2-(4-acetyl-2-methoxyphenoxy)acetate 在 硝酸 、 乙酸酐 、 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 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 生成 2-(4-acetyl-2-methoxy-5-nitro-phenoxy)-N-(2-{2-[2-(2-azido-ethoxy)ethoxy]ethoxy}ethyl)acetamide
  参考文献：
  名称：

  [EN] ANTHRACYCLINE PRODRUGS AND METHODS OF MAKING AND USING THE SAME
  [FR] PROMÉDICAMENTS D'ANTHRACYNE ET PROCÉDÉS DE PRODUCTION ET D'UTILISATION DE CES DERNIERS

  摘要：

  用于预防和治疗癌症的具有治疗效果的前药化合物，以及含有这些化合物的药物组合物，以及制备和使用这些化合物的方法。

  公开号：

  WO2016176332A1

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。
• Construction of a Photoactivated Insulin Depot
  作者：Piyush K. Jain、Dipu Karunakaran、Simon H. Friedman

  DOI：10.1002/anie.201207264

  日期：2013.1.28

  Light controlled: A material that allows for insulin to be released in a controlled fashion by using light was prepared. A subcutaneous reservoir of such materials could allow for the non‐invasive control of blood sugar. Insulin (blue in picture) was linked to an insoluble resin (green) through a photocleavable linker (red). Native insulin is released following a first‐order process in response to

  光控：制备了允许通过使用光以受控方式释放胰岛素的材料。这种材料的皮下储存器可允许无创控制血糖。胰岛素（图中蓝色）通过光可裂解的连接物（红色）与不溶性树脂（绿色）连接。一阶过程之后，天然胰岛素会释放出来，以响应来自LED的光脉冲。
• Photocleavable drug conjugates
  申请人：THE CURATORS OF THE UNIVERSITY OF MISSOURI

  公开号：US10159735B2

  公开（公告）日：2018-12-25

  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.

  用于形成药物储藏库的新型光可溶解药物共轭物由附着在光可溶解基团上的药物组成。在一个实施方案中，药物通过可光裂解基团与聚合物链连接，形成可光裂解的药物-聚合物共轭物，一般形成药库基质。在另一个实施方案中，药物通过可光裂解基团与自身交联，形成可光裂解的药物共轭物，一般形成药库。
• 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.
• 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.