ungeremine hydrochloride | 2121-16-6

• 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: ungeremine hydrochloride
• 英文别名: Lycobetaine chloride；5,7-dioxa-12-azoniapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9,11,15(19),16-heptaen-17-ol;chloride
• CAS: 2121-16-6
• 化学式: C₁₆H₁₂NO₃*Cl
• 分子量: 301.729
• InChiKey: FYVINXPNJCVJEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ungeremine hydrochloride 在 sodium tetrahydroborate 、 水 作用下， 生成 4,5-dihydro-7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-2-ol
  参考文献：
  名称：

  Alkaloids of the Amaryllidaceae. VI. The Action of Oxidizing Agents on Lycorine and Caranine¹

  摘要：

  DOI：

  10.1021/ja01627a032
• 作为产物：
  描述：

  ungeremine 在 盐酸 作用下， 以 水 为溶剂， 以15 mg的产率得到ungeremine hydrochloride
  参考文献：
  名称：

  Ungeremine and Its Hemisynthesized Analogues as Bactericides against Flavobacterium columnare

  摘要：

  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.

  DOI：

  10.1021/jf304586j

文献信息

• Alkaloids of the Amaryllidaceae. VI. The Action of Oxidizing Agents on Lycorine and Caranine¹
  作者：H. M. Fales、E. W. Warnhoff、W. C. Wildman

  DOI：10.1021/ja01627a032

  日期：1955.11
• 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.