21080-31-9Relevant articles and documents
Structural modification of sanguinarine and chelerythrine and their in vitro acaricidal activity against Psoroptes cuniculi
Miao, Fang,Yang, Xin-Juan,Ma, Yan-Ni,Zheng, Feng,Song, Xiao-Ping,Zhou, Le
, p. 1508 - 1513 (2013/02/23)
Sanguinarine (1) and chelerythrine (2) are two quaternary benzo[c]phenanthridine alkaloids (QBAs). Eighteen derivatives of 1 and 2 were synthesized by modification of C=N+ bond and evaluated for their in vitro acaricidal activity against Psoroptes cuniculi , a mange mite. A new method was developed to prepare 6-alkoxy dihydro derivatives of 1 and 2 (1a-e, 2a-e). Among all the compounds, only 6-alkoxy dihydrosanguinarines (1a-e) showed significant acaricidal activity at 5.0 mg/mL and 1a possessed the strongest activity (50% lethal concentrations (LC50)=339.70±0.75 mg/L, 50% lethal time ( LT50)=6.53±0.04 h), comparable with a standard drug ivermectin (LC50=168.19±11.79 mg/L, LT 50=16.54±0.11 h). The iminium moiety in 1 and 2 was proven to be the determinant for their acaricidal properties. 6-Alkoxy dihydro derivatives (1a-e, 2a-e) were prodrugs of 1 and 2. Compared with 7,8-dimethoxy groups, 7,8-methylenedioxy group was able to significantly improve the bioactivity. The present results suggested that QBAs are promising candidates or lead compounds for the development of new isoquinoline acaricidal agents.
Structural modification of sanguinarine and chelerythrine and their antibacterial activity
Miao, Fang,Yang, Xin-Juan,Zhou, Le,Hu, Hai-Jun,Zheng, Feng,Ding, Xu-Dong,Sun, Dong-Mei,Zhou, Chun-Dong,Sun, Wei
experimental part, p. 863 - 875 (2011/07/08)
In this study, five derivatives of sanguinarine (1) and chelerythrine (2) were prepared, with 1 and 2 as starting materials, by reduction, oxidation and nucleophilic addition to the iminium bond C=N+. The structures of all compounds were elucidated on account of their MS, 1H-NMR and 13C-NMR data. The antibacterial activities of all compounds were screened, using Staphylococcus aureus, Escherichia coli, Aeromonas hydrophila and Pasteurella multocida as test bacteria. The minimum bacteriostatic concentration and minimum bactericidal concentration of the active compounds were determined by the turbidity method. The structure-activity relationships of 1 and 2 were discussed. The results showed that 1, 2 and their pseudoalcoholates were found to be potent inhibitors to S. aureus, E. coli and A. hydrophila, while the other derivatives were found to be inactive. The pseudoalcoholates might be the prodrugs of 1 and 2. The iminium bond in the molecules of 1 or 2 was the determinant for antibacterial activity, and the substituents at the 7 and 8 positions influenced the antibacterial activities of 1 and 2 against different bacteria.
Chemical Transformation of Protoberberines. Part 9. A Biomimetic Synthesis of Oxychelerythrine, Dihydrochelerythrine, and Chelerythrine from Berberine
Hanaoka, Miyoji,Motonishi, Toshio,Mukai, Chisato
, p. 2253 - 2256 (2007/10/02)
Fully aromatised benzophenanthridine alkaloids, oxychelerythrine (4), dihydrochelerythrine (9), and chelerythrine (10) have been efficiently synthesized from berberine (1), a protoberberine alkaloid, via oxidative C(6)-N bond cleavage, followed by recyclisation betwen the C-6 and C-13 positions of (1) by a biogenetic process.
