5-tert-Butoxycarbonylamino-4-oxo-pentanoic acid 2,2,3,3,4,4,4-heptafluoro-butyl ester | 769137-39-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 5-tert-Butoxycarbonylamino-4-oxo-pentanoic acid 2,2,3,3,4,4,4-heptafluoro-butyl ester
• CAS: 769137-39-5
• 化学式: C₁₄H₁₈F₇NO₅
• 分子量: 413.289
• InChiKey: UCSRDMXYJVAKMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-tert-Butoxycarbonylamino-4-oxo-pentanoic acid 2,2,3,3,4,4,4-heptafluoro-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 2,2,3,3,4,4,4-Heptafluorobutyl 5-amino-4-oxopentanoate;hydrochloride
  参考文献：
  名称：

  New 5-Aminolevulinic Acid Esters—Efficient Protoporphyrin Precursors for Photodetection and Photodynamic Therapy¶

  摘要：

  Photodetection (PD) and photodynamic therapy (PDT) with 5-aminolevulinic acid (ALA)-induced protoporphyrin IX (PPIX) accumulation are approaches to detect and treat dysplasia and early cancer in the gastrointestinal tract and in the urinary bladder. Because ALA-induced PPIX production is limited, we synthesized ALA ester hydrochlorides 3-22 and tested them in two different in vitro models (gastrointestinal tract: HT29-CCD18; urinary bladder: J82-UROTSA). PPIX accumulation after incubation with 0.12 mmol/L for 3 h and PPIX accumulation as a function of different incubation times were measured using flow cytometry. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assays were performed to check cellular dark toxicity. Phototoxicity after irradiation was tested. ALA nonafluorolhexylester hydrochloride 11, ALA thiolhexylester hydrochloride 13 and ALA dibenzyldiester dihydrochloride 19 induced appreciably increased PPIX levels and showed improved phototoxicity compared with the references ALA hydrochloride 1, ALA hexylester hydrochloride 3 and ALA benzylester hydrochloride 4. Thus, the new compounds 11, 13 and 19 are promising compounds for PD and PDT.

  DOI：

  10.1562/0031-8655(2003)078<0481:naaepp>2.0.co;2
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 68.0h， 生成 5-tert-Butoxycarbonylamino-4-oxo-pentanoic acid 2,2,3,3,4,4,4-heptafluoro-butyl ester
  参考文献：
  名称：

  New 5-Aminolevulinic Acid Esters—Efficient Protoporphyrin Precursors for Photodetection and Photodynamic Therapy¶

  摘要：

  Photodetection (PD) and photodynamic therapy (PDT) with 5-aminolevulinic acid (ALA)-induced protoporphyrin IX (PPIX) accumulation are approaches to detect and treat dysplasia and early cancer in the gastrointestinal tract and in the urinary bladder. Because ALA-induced PPIX production is limited, we synthesized ALA ester hydrochlorides 3-22 and tested them in two different in vitro models (gastrointestinal tract: HT29-CCD18; urinary bladder: J82-UROTSA). PPIX accumulation after incubation with 0.12 mmol/L for 3 h and PPIX accumulation as a function of different incubation times were measured using flow cytometry. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assays were performed to check cellular dark toxicity. Phototoxicity after irradiation was tested. ALA nonafluorolhexylester hydrochloride 11, ALA thiolhexylester hydrochloride 13 and ALA dibenzyldiester dihydrochloride 19 induced appreciably increased PPIX levels and showed improved phototoxicity compared with the references ALA hydrochloride 1, ALA hexylester hydrochloride 3 and ALA benzylester hydrochloride 4. Thus, the new compounds 11, 13 and 19 are promising compounds for PD and PDT.

  DOI：

  10.1562/0031-8655(2003)078<0481:naaepp>2.0.co;2