zefbetaine | 105708-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: zefbetaine
• 英文别名: 10-Hydroxy-9-methoxy-4,5-dihydropyrrolo[3,2,1-de]phenanthridin-6-ium-2-olate；14-hydroxy-5-methoxy-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,5,7,12(16),13-hexaen-4-one
• CAS: 105708-78-9
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: KAEIXCUGLNXMQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Pseudolycorine 在 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 zefbetaine
  参考文献：
  名称：

  Two betaine-type alkaloids from Egyptian Pancratium maritimum

  摘要：

  Two 2-oxyphenanthridinium alkaloids have been isolated from Egyptian Pancratium maritimum and identified as ungeremine and zefbetaine using spectroscopic and chemical methods. The identification of zefbetaine was supported by its partial synthesis from pseudolycorine and by comparison with its unnatural isomer, isozefbetaine, which was in turn prepared from sternbergine.

  DOI：

  10.1016/0031-9422(92)80381-n

文献信息

• Ungeremine and Its Hemisynthesized Analogues as Bactericides against Flavobacterium columnare
  作者：Kevin K. Schrader、Fabiana Avolio、Anna Andolfi、Alessio Cimmino、Antonio Evidente

  DOI：10.1021/jf304586j

  日期：2013.2.13

  The Gram-negative bacterium Flavobacterium columnare is the cause of columnaris disease, which can occur in channel catfish (Ictalurus punctatus). In a previous study, the betaine-type alkaloid ungeremine, 1, obtained from Pancratium maritimum L. was found to have strong antibacterial activity against F. columnare. In this study, analogues of 1 were evaluated using a rapid bioassay for activity against F. columnare to determine if the analogues might provide greater antibacterial activity and to determine structure-activity relationships of the test compounds. Several ungeremine analogues were prepared by hydrochlorination of the alkaloid and by selenium dioxide oxidation of both lycorine, 7, and pseudolycorine, 8, which yielded the isomer of ungeremine, 3, and zefbetaine, 4, respectively. The treatment of lycorine with phosphorus oxychloride allowed the synthesis of an anhydrolycorine lactam, 5, showing, with respect to 1, the deoxygenation and oxygenation of C-2 and C-7 of the C and B rings, respectively. The results of the structure-activity relationship studies showed that the aromatization of the C ring and the oxidation to an azomethine group of C-7 of the B ring are structural features important for antibacterial activity. In addition, the position of the oxygenation of the C ring as well as the presence of the 1,3-dioxole ring joined to the A ring of the pyrrolo[de]phenanthridine skeleton also plays a significant role in imparting antibacterial activity. On the basis of 24-h 50% inhibition concentration (IC50) results, ungeremine hydrochloride, 2, was similar in toxicity to 1, whereas 5 had the lowest activity. Analogue 2 is soluble in water, which may provide the benefit for use as an effective feed additive or therapeutant compared to ungeremine.