伪石蒜碱 | 29429-03-6

• 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
• 中文名称: 伪石蒜碱
• 英文名称: pseudolycorine
• 英文别名: Pseudolycorin；(1S,14S,15S,16S)-5-methoxy-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-2,4,6,12-tetraene-4,14,15-triol
• CAS: 29429-03-6
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: CKAHWDNDUGDSLE-ARLBYUKCSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  伪石蒜碱 在 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以5 mg的产率得到zefbetaine
  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

• Natural compounds and fibrosis
  申请人：MEDIZINISCHE HOCHSCHULE HANNOVER (MHH)

  公开号：US11185539B2

  公开（公告）日：2021-11-30

  The present invention relates to an inhibitor of miR-671-5p for use in a method of preventing or treating fibrosis. Further, the present invention encompasses a kit comprising said inhibitor of miR-671-5p. The present invention also relates to an in vitro method for identifying a compound for preventing or treating fibrosis.

  本发明涉及一种用于预防或治疗纤维化方法的 miR-671-5p 抑制剂。此外，本发明还包括一种包含所述 miR-671-5p 抑制剂的试剂盒。本发明还涉及一种用于鉴定预防或治疗纤维化的化合物的体外方法。
• NATURAL COMPOUNDS AND FIBROSIS
  申请人：MEDIZINISCHE HOCHSCHULE HANNOVER (MHH)

  公开号：US20190350923A1

  公开（公告）日：2019-11-21

  The present invention relates to an inhibitor of miR-671-5p for use in a method of preventing or treating fibrosis. Further, the present invention encompasses a kit comprising said inhibitor of miR-671-5p. The present invention also relates to an in vitro method for identifying a compound for preventing or treating fibrosis.
• [EN] NATURAL COMPOUNDS AND FIBROSIS<br/>[FR] COMPOSÉS NATURELS ET FIBROSE
  申请人：MEDIZINISCHE HOCHSCHULE HANNOVER MHH

  公开号：WO2018141678A1

  公开（公告）日：2018-08-09

  The present invention relates to an inhibitor of miR-671-5p for use in a method of preventing or treating fibrosis. Further, the present invention encompasses a kit comprising said inhibitor of miR-671-5p. The present invention also relates to an in vitro method for identifying a compound for preventing or treating fibrosis.