ungeremine | 97438-92-1

• 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
• 英文别名: 2-hydroxy-4,5-dihydro-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridinium；2-oxyphenanthridinium betaine；Ungerimine；2-hydroxy-4,5-dihydro-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridinylium betaine；2-Hydroxy-4,5-dihydro-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridinylium-betain；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-olate
• CAS: 97438-92-1
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: DFQOXFIPAAMFAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 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：
  45.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 selenium(IV) oxide 、 乙醇 作用下， 生成 ungeremine
  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

文献信息

• Concise syntheses of the amaryllidaceae alkaloids ungerimine and hippadine via the suzuki aryl-aryl cross coupling reaction
  作者：M.A. Siddiqui、V. Snieckus

  DOI：10.1016/0040-4039(90)80006-8

  日期：1990.1

  Short syntheses of the betaine alkaloid ungerimine (1) and the lactam alkaloid hippadine (4) based on aryl boronic acid - aryl halide cross coupling methodology are described.

  描述了基于芳基硼酸-芳基卤化物交叉偶合方法的甜菜碱生物碱非甾体胺（1）和内酰胺生物碱河马碱（4）的短合成。
• Total synthesis of the amaryllidaceae alkaloid ungeremine
  作者：Urs Lauk、Doris Dürst、Walter Fischer

  DOI：10.1016/s0040-4039(00)71219-6

  日期：1991.1

  The synthesis of the aromatic Amaryllidaceae alkaloid ungeremine 1 with a new type of radical cyclisation as the key step is reported.

  报道了以新型自由基环化为关键步骤的芳基芳科植物生物碱紫菜碱1的合成。
• Occurrence of two epimeric alkaloids and metabolism compared with lycorine in Crinum latifolium
  作者：Shibnath Ghosal、Sankara Unnikrishnan、Sushil K. Singh

  DOI：10.1016/s0031-9422(00)98030-0

  日期：1989.1
• Alkaloids of zephyranthes flava
  作者：Shibnath Ghosal、Sushil K. Singh、Radhey S. Srivastava

  DOI：10.1016/s0031-9422(00)81187-5

  日期：1986.7
• An application of the photocyclization reaction of schiff bases to the synthesis of a phenanthridine alkaloid
  作者：Tadamasa Onaka、Yoshihiro Kanda、Mitsutaka Natsume

  DOI：10.1016/s0040-4039(01)82438-2

  日期：1974.1