berberine bromide | 57231-67-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: berberine bromide
• 英文别名: 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinylium; bromide；Berberinbromid；16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;bromide
• CAS: 57231-67-1
• 化学式: Br*C₂₀H₁₈NO₄
• 分子量: 416.271
• InChiKey: GGWPMWVZFWDNKK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  berberine bromide 在 四氯苯醌 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 22.0~180.0 ℃ 、4.0 kPa 条件下， 反应 1.0h， 生成 19-methoxy-8,10,21-trioxa-22λ⁶-thia-2-azahexacyclo[14.7.1.₀^2,14.0⁵,¹³.0^7,11.0^20,24]tetracosa-1(23),5,7(11),12,14,16,18,20(24)-octaene-22,22-dione
  参考文献：
  名称：

  发现新型磺内酯小Ber碱衍生物作为有希望的Tdp1抑制剂。

  摘要：

  小ber红素与脂肪族磺酰氯反应制得了一种新型的小ine碱衍生物。新的多环化合物具有磺基环缩合到原小ber碱核心的C和D环上。开发了反应条件以促进高产率的磺内酯的形成而没有副产物的形成。因此，显示出试剂的添加顺序会影响反应产物的组成：将硫代氯化物添加到小ine红素中时，其相应的9- O-主要形成磺酸盐；当将小ber红素添加到预生成的亚砜中时，磺内酯是唯一的产品。该反应显示为立体选择性进行，并且通过2D NMR光谱法确认了循环构型。研究了合成的磺内酯及其12个溴代类似物对DNA修复酶酪氨酰DNA磷酸二酯酶1（Tdp1）（潜在的抗肿瘤治疗的重要靶标）的抑制活性。与无环类似物和9- O相比，所有衍生物在微摩尔和亚微摩尔范围内均具有活性-磺酸盐，它是不活泼的。使用分子模型确定了磺内酯循环和溴取代基与酶结合的重要性。活性抑制剂对HeLa癌细胞系大多无毒，几种配体与拓扑替康（一种拓扑异构酶1毒物）在临床

  DOI：

  10.3390/molecules26071945
• 作为产物：
  描述：

  四氢小檗碱 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 生成 berberine bromide
  参考文献：
  名称：

  Rao,K.V.; Kapicak,L.S., Journal of Heterocyclic Chemistry, 1976, vol. 13, p. 1073 - 1077

  摘要：

  DOI：

文献信息

• 8,13a-Propanoberbines. III. Reaction of acetoneberberine type enamine with alkyl halide.
  作者：SHUNSUKE NARUTO、HARUKI NISHIMURA、HIDEHIKO KANEKO

  DOI：10.1248/cpb.23.1271

  日期：——

  The reaction of acetoneberberine (I) with methyl iodide was found to give 8, 13a-(2'-oxopropano)-13, 13-dimethylberbine derivative (IV) and 8, 13a-(2'-oxopropano)-13-methylberbine derivative (V) as side products together with the expected 13-methyl-berberinium (II) and berberinium iodide (III). Analogous reaction of I with allyl bromide gave rise to 8, 13a-(2'-oxopropano)-13, 13-diallylberbine derivative (XI). The structures of products were deduced from chemical and spectral data.

  丙酮小檗碱(I)与碘甲烷反应生成8, 13a-(2'-氧代丙烷)-13, 13-二甲基小檗碱衍生物(IV)和8, 13a-(2'-氧代丙烷)-13-甲基小檗碱衍生物(V) 与预期的 13-甲基-小檗 (II) 和碘化小檗 (III) 一起作为副产物。 I与烯丙基溴的类似反应产生8, 13a-(2'-氧代丙烷)-13, 13-二烯丙基小檗碱衍生物(XI)。从化学和光谱数据推导出产物的结构。
• A composition for preventing plant diseases resulted from infection of plant pathogens and a method for preparing the same
  申请人：Kang Hoon Serg

  公开号：US20060228428A1

  公开（公告）日：2006-10-12

  The present invention relates to a composition for preventing at least one plant disease resulted from infection of plant pathogens and a method for preparing the same. Particularly, the composition contains extract of at least one plant selected from the group consisting of Coptis chinensis Franch., Phellodendron genus plant, Sanguinaria canadensis and Chelidonium majus var. asiaticum which are natural plants having anti-plant pathogen activity or berberine which is purified therefrom. The composition of the present invention can be effectively used for preventing disease pathogens such as plant powdery mildew, anthracnose of pepper, damping-off of cucumber and gray mold rot of strawberry resulted from infection of plant pathogens such as Colletrotrichum gloeosporiodes, Pythium ultimum or Botrytis cinerea . For an alternative method for preparing the composition comprising berberine and/or derivatives thereof, the present invention provides various optimal culture condition and two phases cultivation methods using Phellodendron genus plant.

  本发明涉及一种用于预防植物病原体感染导致的至少一种植物病害的组合物及其制备方法。特别是，该组合物含有至少一种选自以下组别的植物的提取物 黄连 黄柏 黄柏 属植物 黄柏属植物 和 诃子 var. 小檗碱 或从中提纯的小檗碱。本发明的组合物可有效地用于预防植物白粉病、辣椒炭疽病、黄瓜受潮病和草莓灰霉病等病害病原体，这些病害病原体是由植物病原体感染引起的，如 球孢子菌、超微粉疫霉菌 或 灰霉病菌 .对于制备包含小檗碱和/或其衍生物的组合物的另一种方法，本发明提供了各种最佳培养条件和两阶段培养方法，使用的培养基包括 黄柏 属植物。
• IKEKAWA, TETSURO;SHIMADA, FUMITAKE;CYONG, JONG-CHOL;UEBABA, KAZUO
  作者：IKEKAWA, TETSURO、SHIMADA, FUMITAKE、CYONG, JONG-CHOL、UEBABA, KAZUO

  DOI：——

  日期：——
• METHOD FOR PREVENTING PLANT DISEASES
  申请人：KANG Hoon Serg

  公开号：US20080175927A1

  公开（公告）日：2008-07-24

  The present invention relates to a composition for preventing at least one plant disease resulted from infection of plant pathogens and a method for preparing the same. Particularly, the composition contains extract of at least one plant selected from the group consisting of Coptis chinensis Franch., Phellodendron genus plant, Sanguinaria canadensis and Chelidonium majus var. asiaticum which are natural plants having anti-plant pathogen activity or berberine which is purified therefrom. The composition of the present invention can be effectively used for preventing disease pathogens such as plant powdery mildew, anthracnose of pepper, damping-off of cucumber and gray mold rot of strawberry resulted from infection of plant pathogens such as Colletrotrichum gloeosporiodes, Pythium ultimum or Botrytis cinerea. For an alternative method for preparing the composition comprising berberine and/or derivatives thereof, the present invention provides various optimal culture condition and two phases cultivation methods using Phellodendron genus plant.
• Rao,K.V.; Kapicak,L.S., Journal of Heterocyclic Chemistry, 1976, vol. 13, p. 1073 - 1077
  作者：Rao,K.V.、Kapicak,L.S.

  DOI：——

  日期：——