3-(benzyloxy)-N-methyl-4-oxo-4H-pyran-2-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(benzyloxy)-N-methyl-4-oxo-4H-pyran-2-carboxamide
• 英文别名: N-methyl-4-oxo-3-phenylmethoxypyran-2-carboxamide
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: CWWOVAYTIHBDBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(benzyloxy)-N-methyl-4-oxo-4H-pyran-2-carboxamide 在 4-二甲氨基吡啶 、 5%-palladium/activated carbon 、 氢气 、 氯化苄 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 19.0h， 生成 5-((6-(3-hydroxy-2-(methylcarbamoyl)-4-oxopyridin-1(4H)-yl)hexyl)oxy)-2,5-dioxopentan-1-aminium chloride
  参考文献：
  名称：

  5-氨基酮戊酸/3-羟基吡啶酮缀合物及其制备 法和用途

  摘要：

  本发明公开了5‑氨基酮戊酸与3‑羟基吡啶‑4‑酮的缀合物，该缀合物是5‑氨基酮戊酸与铁螯合剂3‑羟基吡啶‑4‑酮的缀合物，分别为ALA‑HPO缀合物1‑4。本发明还同时公开了上述5‑氨基酮戊酸与3‑羟基吡啶‑4‑酮的缀合物的制备方法及其用途，其能用作制备光动力学治疗药物，也能用于制备治疗皮肤癌、肺癌或尖锐湿疣的药物。

  公开号：

  CN106478493B
• 作为产物：
  描述：

  度鲁特韦中间体-3 在 sodium hypochlorite 、 氨基磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 3-(benzyloxy)-N-methyl-4-oxo-4H-pyran-2-carboxamide
  参考文献：
  名称：

  Hydroxypyridinone and 5-Aminolaevulinic Acid Conjugates for Photodynamic Therapy

  摘要：

  Photodynamic therapy (PDT) is a promising treatment strategy for malignant and nonmalignant lesions. 5-Aminolaevulinic acid (ALA) is used as a precursor of the photosensitizer, protoporphyrin IX (PpIX), in dermatology and urology. However, the effectiveness of ALA-PDT is limited by the relatively poor bioavailability of ALA. and rapid conversion of PpIX to haem. The main goal of this study was to prepare and investigate a library of single conjugates designed to coadminister the bioactive agents. ALA and hydroxypyridinone (HPO) iron chelators. A significant increase in intracellular PpIX levels was observed in all cell lines tested when compared to the administration of ALA alone. The higher PpIX levels observed using the conjugates correlated well with the observed phototoxicity following exposure of cells to light. Passive diffusion appears to be the main mechanism for the majority of ALA-HPOs investigated. This study demonstrates that ALA-HPOs significantly enhance phototherapeutic metabolite foiniation and phototoxicity.

  DOI：

  10.1021/acs.jmedchem.7b00346

文献信息

• 5-氨基酮戊酸/3-羟基吡啶酮缀合物及其制备 法和用途
  申请人：浙江工商大学

  公开号：CN106478493B

  公开（公告）日：2018-12-11

  本发明公开了5‑氨基酮戊酸与3‑羟基吡啶‑4‑酮的缀合物，该缀合物是5‑氨基酮戊酸与铁螯合剂3‑羟基吡啶‑4‑酮的缀合物，分别为ALA‑HPO缀合物1‑4。本发明还同时公开了上述5‑氨基酮戊酸与3‑羟基吡啶‑4‑酮的缀合物的制备方法及其用途，其能用作制备光动力学治疗药物，也能用于制备治疗皮肤癌、肺癌或尖锐湿疣的药物。
• METALLOPROTEIN INHIBITORS
  申请人：Puerta T. David

  公开号：US20070117848A1

  公开（公告）日：2007-05-24

  The present invention relates to metalloprotein inhibitors comprising: a. an organic substituent and at least one zinc binding group (ZBG) covalently attached thereto; or b. a ZBG substituted by a side chain wherein the ZBG is of formula (I): wherein X is O or S and each R 1 , R 2 , R 3 , and R 4 is individually hydrogen or an organic radical. The metalloprotein inhibitors are useful for preventing or treating a pathological disease, condition, or symptom that is associated with pathological metalloprotein activity and/or that is alleviated by inhibition of said activity.

  本发明涉及金属蛋白酶抑制剂，包括：a. 有机取代基和至少一个锌结合基团（ZBG）共价连接在一起；或者b. 通过侧链取代的ZBG，其中ZBG的公式为（I）：其中X为O或S，每个R1、R2、R3和R4分别为氢或有机基团。这些金属蛋白酶抑制剂可用于预防或治疗与病理性金属蛋白酶活性相关的病理性疾病、状况或症状，或者通过抑制该活性缓解的病理性疾病、状况或症状。
• US7579486B2
  申请人：——

  公开号：US7579486B2

  公开（公告）日：2009-08-25
• US7786316B2
  申请人：——

  公开号：US7786316B2

  公开（公告）日：2010-08-31
• Hydroxypyridinone and 5-Aminolaevulinic Acid Conjugates for Photodynamic Therapy
  作者：Sinan Battah、Robert C. Hider、Alexander J. MacRobert、Paul S. Dobbin、Tao Zhou

  DOI：10.1021/acs.jmedchem.7b00346

  日期：2017.4.27

  Photodynamic therapy (PDT) is a promising treatment strategy for malignant and nonmalignant lesions. 5-Aminolaevulinic acid (ALA) is used as a precursor of the photosensitizer, protoporphyrin IX (PpIX), in dermatology and urology. However, the effectiveness of ALA-PDT is limited by the relatively poor bioavailability of ALA. and rapid conversion of PpIX to haem. The main goal of this study was to prepare and investigate a library of single conjugates designed to coadminister the bioactive agents. ALA and hydroxypyridinone (HPO) iron chelators. A significant increase in intracellular PpIX levels was observed in all cell lines tested when compared to the administration of ALA alone. The higher PpIX levels observed using the conjugates correlated well with the observed phototoxicity following exposure of cells to light. Passive diffusion appears to be the main mechanism for the majority of ALA-HPOs investigated. This study demonstrates that ALA-HPOs significantly enhance phototherapeutic metabolite foiniation and phototoxicity.