2-甲氧基乙基5-氨基-4-氧代戊酸酯盐酸盐(1:1) | 321837-75-6

• 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
• 中文名称: 2-甲氧基乙基5-氨基-4-氧代戊酸酯盐酸盐(1:1)
• 英文名称: 2-Methoxyethyl 5-amino-4-oxopentanoate Hydrochloride
• 英文别名: 2-methoxyethyl 5-amino-4-oxopentanoate;hydrochloride
• CAS: 321837-75-6
• 化学式: C₈H₁₅NO₄*ClH
• 分子量: 225.672
• InChiKey: IXKYKGMDWDAILY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.23
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氨基乙酰丙酸盐酸盐 以 乙二醇甲醚 为溶剂， 以1.25 g (93%)的产率得到2-甲氧基乙基5-氨基-4-氧代戊酸酯盐酸盐(1:1)
  参考文献：
  名称：

  Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy

  摘要：

  该发明提供了用于光化疗或诊断的化合物，所述化合物为5-氨基丙酸的支链烷基酯或取代烷基酯，或其衍生物或药用可接受的盐。具体而言，该发明提供了式(I)的化合物：R2N—CH2COCH2CH2CO—OR1（其中R1代表可选择取代的支链烷基（例如C5-30烷基）基团，或取代烷基基团；R2，每个可能相同或不同，代表氢原子或可选择取代的烷基基团，优选为基团R1；其中所述取代基被选择自羟基、烷氧基、酰氧基、烷氧羰氧基、氨基、芳基、硝基、氧代、氟代、—SR3、—NR32和PR32基团，每个烷基基团可选择地被一个或多个O—、—NR3—、—S—或—PR3—基团中断；R3代表氢原子或C1-6烷基基团）及其盐，用于诊断和治疗身体外部或内部表面的异常或疾病的光化疗，以及执行该发明的产品和工具包。

  公开号：

  US20040106679A1

文献信息

• Ethylene Glycol and Amino Acid Derivatives of 5-Aminolevulinic Acid as New Photosensitizing Precursors of Protoporphyrin IX in Cells
  作者：Yann Berger、Alain Greppi、Olivier Siri、Reinhard Neier、Lucienne Juillerat-Jeanneret

  DOI：10.1021/jm000981q

  日期：2000.12.1

  of cancer and is synthesized intracellularly from aminolevulinic acid (ALA) precursors. To evaluate means to specifically target ALA derivatives to defined cells, we have synthesized and characterized ethylene glycol esters and amino acid pseudodipeptide derivatives of ALA as potential specific substrates for cellular esterases and aminopeptidases, respectively. The PpIX formation induced by these

  原卟啉IX（PpIX）在癌症的光动力检测和治疗（PDT）中用作光敏剂，由氨基乙酰丙酸（ALA）前体在细胞内合成。为了评估将ALA衍生物特异性靶向特定细胞的方法，我们合成并表征了ALA的乙二醇酯和氨基酸假二肽衍生物分别作为细胞酯酶和氨基肽酶的潜在特异性底物。使用人类和大鼠的癌细胞系和内皮细胞培养物研究了由这些产物诱导的PpIX形成。这些化合物在没有光照的情况下的细胞毒性也得到了控制。结果表明，乙二醇酯可以诱导高水平的PpIX，并在低于其细胞毒性阈值的浓度下有用。
• NEW ESTERS OF 5-AMINOLEVULINIC ACID AND THEIR USE AS PHOTOSENSITIZING COMPOUNDS IN PHOTOCHEMOTHERAPY
  申请人：Gierskcky E. Karl

  公开号：US20050107471A1

  公开（公告）日：2005-05-19

  The present invention relates to compounds being esters of 5-aminolevulinic acids or pharmaceutically acceptable salts thereof, including compounds of formula (I) R 2 2 N—CH 2 COCH 2 —CH 2 CO—OR 1 (wherein R 1 may represent alkyl optionally substituted by hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, amino, aryl, oxo or fluoro groups and optionally interrupted by oxygen, nitrogen, sulphur or phosphorus atoms; and R 2 represents a hydrogen atom or a group R 1 , and both R 2 groups may be the identical or different), and their use in diagnosis and photochemotherapy of disorders or abnormalities of external or internal surfaces of the body, and products and kits for performing the invention.

  本发明涉及5-氨基戊酸酯化合物或其药学上可接受的盐，包括式(I)的化合物R22N-CH2COCH2-CH2CO-OR1（其中R1可能代表烷基，可选地被羟基，烷氧基，酰氧基，烷氧羰氧基，氨基，芳基，氧化物或氟基取代，并可由氧，氮，硫或磷原子中断; R2表示氢原子或R1基团，且两个R2基团可以相同或不同），以及它们在诊断和光化学治疗身体内外表面的疾病或异常中的应用，以及用于执行本发明的产品和工具包。
• New 5-Aminolevulinic Acid Esters—Efficient Protoporphyrin Precursors for Photodetection and Photodynamic Therapy¶
  作者：H. Brunner、F. Hausmann、R. Knuechel

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

  日期：——

  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.
• ESTERS OF 5-AMINOLEVULINIC ACID AS PHOTOSENSITIZING AGENTS IN PHOTOCHEMOTHERAPY
  申请人：Photocure ASA

  公开号：EP1313695B1

  公开（公告）日：2006-12-27
• US6992107B1
  申请人：——

  公开号：US6992107B1

  公开（公告）日：2006-01-31