2-(3-(benzyloxy)-2-ethyl-4-oxopyridin-1(4H)-yl)ethyl 5-(((benzyloxy)carbonyl)amino)-4-oxopentanoate | 1574379-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-(benzyloxy)-2-ethyl-4-oxopyridin-1(4H)-yl)ethyl 5-(((benzyloxy)carbonyl)amino)-4-oxopentanoate
• 英文别名: 2-(3-(Benzyloxy)-2-ethyl-4-oxopyridin-1(4H)-yl)ethyl 5-(benzyloxycarbonylamino)-4-oxopentanoate；2-(2-ethyl-4-oxo-3-phenylmethoxypyridin-1-yl)ethyl 4-oxo-5-(phenylmethoxycarbonylamino)pentanoate
• CAS: 1574379-22-8
• 化学式: C₂₉H₃₂N₂O₇
• 分子量: 520.582
• InChiKey: GRTYJFQHNBDOTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(3-(benzyloxy)-2-ethyl-4-oxopyridin-1(4H)-yl)ethyl 5-(((benzyloxy)carbonyl)amino)-4-oxopentanoate 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以96%的产率得到1-(2-(5-amino-4-oxoientanoyloxy)ethyl)-2-ethyl-3,4-dihydroxyiyridinium chloride hydrochloride
  参考文献：
  名称：

  [EN] PYRIDINONE COMPOUNDS FOR USE IN PHOTODYNAMIC THERAPY
  [FR] COMPOSÉS DE PYRIDINONE DESTINÉS À ÊTRE UTILISÉS EN THÉRAPIE PHOTODYNAMIQUE

  摘要：

  一种化合物，其化学式为（I）或其任何盐：其中R1是一种碳原子数为1至6的烷基基团，R2是氢或一种碳原子数为1至6的烷基基团，R3是氢或一种碳原子数为1至6的烷基基团，n为0至5之间的整数。

  公开号：

  WO2014033477A1
• 作为产物：
  描述：

  5-氨基乙酰丙酸 在 4-二甲氨基吡啶 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 18.83h， 生成 2-(3-(benzyloxy)-2-ethyl-4-oxopyridin-1(4H)-yl)ethyl 5-(((benzyloxy)carbonyl)amino)-4-oxopentanoate
  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。
• PYRIDINONE COMPOUNDS FOR USE IN PHOTODYNAMIC THERAPY
  申请人：UNIVERSITY OF EXETER

  公开号：US20150210642A1

  公开（公告）日：2015-07-30

  A compound which is a compound of formula (I) or any salt thereof: wherein R1 is a Ci-C6 alkyl group, R2 is H or a Ci-C6 alkyl group, R3 is H or a Ci-C6 alkyl group, and n is an integer from 0 to 5.

  一种化合物，其化学式为（I）或其任何盐：其中R1为Ci-C6烷基基团，R2为H或Ci-C6烷基基团，R3为H或Ci-C6烷基基团，n为0至5之间的整数。
• Pyridinone compounds for use in photodynamic therapy
  申请人：UNIVERSITY OF EXETER

  公开号：US09346758B2

  公开（公告）日：2016-05-24

  A compound which is a compound of formula (I) or any salt thereof: wherein R1 is a Ci-C6 alkyl group, R2 is H or a Ci-C6 alkyl group, R3 is H or a Ci-C6 alkyl group, and n is an integer from 0 to 5.

  一种化合物，其化学式为（I）或其任何盐：其中R1是C1-C6烷基，R2是氢或C1-C6烷基，R3是氢或C1-C6烷基，n是0到5之间的整数。
• US9346758B2
  申请人：——

  公开号：US9346758B2

  公开（公告）日：2016-05-24
• 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.