8,8-Dimethyldihydroberberine | 1244023-77-5

• 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: 8,8-Dimethyldihydroberberine
• 英文别名: 16,17-dimethoxy-14,14-dimethyl-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,15(20),16,18-heptaene;chloride
• CAS: 1244023-77-5
• 化学式: C₂₂H₂₄NO₄*Cl
• 分子量: 401.89
• InChiKey: MDVUKRMJFRYYIF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  8,8-Dimethyldihydroberberin 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.02h， 以207.6 mg的产率得到8,8-Dimethyldihydroberberine
  参考文献：
  名称：

  8,8-Dialkyldihydroberberines with Potent Antiprotozoal Activity

  摘要：

  Semisynthetic 8,8-dialkyldihydroberberines (8,8-DDBs) were found to possess mid- to low-nanomolar potency against Plasmodium falciparum blood-stage parasites, Leishmania donovani intracellular amastigotes, and Trypanosoma brucei brucei bloodstream forms. For example, 8,8-diethyldihydroberberine chloride (5b) exhibited in vitro IC50 values of 77, 100, and 5.3 nM against these three parasites, respectively. In turn, two 8,8-dialkylcanadines, obtained by reduction of the corresponding 8,8-DDBs, were much less potent against these parasites in vitro. While the natural product berberine is a weak DNA binder, the 8,8-DDBs displayed no affinity for DNA, as assessed by changes in the melting temperature of poly(dA.dT) DNA. Selected 8,8-DDBs showed efficacy in mouse models of visceral leishmaniasis and African trypanosomiasis, with 8,8-dimethyldihydroberberine chloride (5a) reducing liver parasitemia by 46% in L. donovani-infected BALB/c mice when given at an intraperitoneal dose of 10 mg/kg/day for five days. The 8,8-DDBs may thus serve as leads for discovering new antimalarial, antileishmanial, and antitrypanosomal drug candidates.

  DOI：

  10.1021/np300638f