3,6-二氢-2,5-吡唑啉胆酸 | 77479-03-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 3,6-二氢-2,5-吡唑啉胆酸
• 英文名称: 2,5-(β-carboxyethyl)dihydropyrazine
• 英文别名: 3,6-dihydropyrazine-2,5-dipropanoic acid；2,5-dicarboxyethyl-3,6-dihydropyrazine；3,3'-(3,6-Dihydropyrazine-2,5-diyl)dipropanoic acid；3-[6-(2-carboxyethyl)-2,5-dihydropyrazin-3-yl]propanoic acid
• CAS: 77479-03-9
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: VYHCBAHHXCYDQC-UHFFFAOYSA-N

物化性质

• 沸点：
  469.7±45.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-二氢-2,5-吡唑啉胆酸 在 air 作用下， 生成 3-[5-(2-羧乙基)吡嗪-2-基]丙酸
  参考文献：
  名称：

  The nonenzymatic cyclic dimerisation of 5-aminolevulinic acid

  摘要：

  The nonenzymatic cyclic dimerisation of 5-aminolevulinic acid (5-ALA) leads to the formation of a pyrazine (3) and, under some circumstances, pseudo-porphobilinogen (1). On the other hand, the enzyme-catalysed process leads to porphobilinogen (PBG). The products of the former reaction were identified from their NMR spectra and mechanisms for their formation are proposed.

  DOI：

  10.1016/s0040-4020(01)80465-8
• 作为产物：
  描述：

  5-氨基乙酰丙酸盐酸盐 在 氮气 作用下， 以 sodium hydroxide 为溶剂， 以95%的产率得到3,6-二氢-2,5-吡唑啉胆酸
  参考文献：
  名称：

  Degradation mechanism and stability of 5‐aminolevulinic acid

  摘要：

  The physiological substance and precursor of the heme synthesis 5-aminolevulinic acid (ALA) is a promising prodrug for photodiagnosis and photodynamic therapy of epithelial tumors, particularly in urological and gynecological tissues. For the clinical use of this substance, a chemically stable and sterile drug formulation is required. In the present study, degradation mechanism of ALA in aqueous solution and possibilities to improve its stability were examined. A capillary electrophoretic method was developed that was suitable for the quantification of ALA and of two degradation products. The intermediate degradation product was 2, 5-dicarboxyethyl-3,6-dihydropyrazine, which was further oxidized to 2,5-dicarboxyethylpyrazine. The structures of the degradation products were proven by (1)H and (13)C nuclear magnetic resonance spectroscopy. ALA degradation was very efficiently inhibited by adjusting the pH of the aqueous solution to a value <5 and by purging with nitrogen. Additives such as antioxidants did not improve the ALA stability. These results demonstrated that low pH ALA aqueous solution may be one possible dosage form to be considered for market introduction.

  DOI：

  10.1002/1520-6017(200010)89:10<1335::aid-jps11>3.0.co;2-#

文献信息

• Reaction of Acetaldehyde with 5-Aminolevulinic Acid &lt;i&gt;via&lt;/i&gt; Dihydropyrazine Derivative
  作者：Toshinori Suzuki、Naoki Yasuhara、Takashi Ueda、Michiyo Inukai、Mitsunobu Mio

  DOI：10.1248/cpb.c14-00694

  日期：——

  (ALA) was incubated with acetaldehyde at neutral pH, a product was generated. This product was identified as 3-ethylpyrazine-2,5-dipropanoic acid (ETPY). ETPY was stable at neutral pH. It has been reported that ALA dimerizes at neutral pH generating 3,6-dihydropyrazine-2,5-dipropanoic acid (DHPY), and subsequently resulting in pyrazine-2,5-dipropanoic acid (PY) by autoxidation. In the present reaction

  当将5-氨基乙酰丙酸（ALA）溶液与乙醛在中性pH下孵育时，生成了产物。该产物被鉴定为3-乙基吡嗪-2，5-二丙酸（ETPY）。ETPY在中性pH下稳定。据报道，ALA在中性pH下二聚，生成3,6-二氢吡嗪-2,5-二丙酸（DHPY），随后通过自氧化反应生成吡嗪-2,5-二丙酸（PY）。在本反应中，由ALA产生的DHPY与乙醛反应，得到ETPY。乙醛注射前3分钟预先给予ALA抑制了乙醛对雄性小鼠的毒性。这些结果表明ALA可用作乙醛的清除剂。
• Degradation mechanism and stability of 5‐aminolevulinic acid
  作者：A. Bunke、O. Zerbe、H. Schmid、G. Burmeister、H. P. Merkle、B. Gander

  DOI：10.1002/1520-6017(200010)89:10<1335::aid-jps11>3.0.co;2-#

  日期：2000.10

  The physiological substance and precursor of the heme synthesis 5-aminolevulinic acid (ALA) is a promising prodrug for photodiagnosis and photodynamic therapy of epithelial tumors, particularly in urological and gynecological tissues. For the clinical use of this substance, a chemically stable and sterile drug formulation is required. In the present study, degradation mechanism of ALA in aqueous solution and possibilities to improve its stability were examined. A capillary electrophoretic method was developed that was suitable for the quantification of ALA and of two degradation products. The intermediate degradation product was 2, 5-dicarboxyethyl-3,6-dihydropyrazine, which was further oxidized to 2,5-dicarboxyethylpyrazine. The structures of the degradation products were proven by (1)H and (13)C nuclear magnetic resonance spectroscopy. ALA degradation was very efficiently inhibited by adjusting the pH of the aqueous solution to a value <5 and by purging with nitrogen. Additives such as antioxidants did not improve the ALA stability. These results demonstrated that low pH ALA aqueous solution may be one possible dosage form to be considered for market introduction.
• The nonenzymatic cyclic dimerisation of 5-aminolevulinic acid
  作者：Anthony R Butler、Sharon George

  DOI：10.1016/s0040-4020(01)80465-8

  日期：1992.1

  The nonenzymatic cyclic dimerisation of 5-aminolevulinic acid (5-ALA) leads to the formation of a pyrazine (3) and, under some circumstances, pseudo-porphobilinogen (1). On the other hand, the enzyme-catalysed process leads to porphobilinogen (PBG). The products of the former reaction were identified from their NMR spectra and mechanisms for their formation are proposed.