title: Synthesis and antimicrobial activity of 3-alkoxyjatrorrhizine derivatives.
abstract: The compounds 3-ethoxy- ( 2), 3-butoxy- ( 3), 3-hexyloxy- ( 4), 3-octyloxy- ( 5), 3-decyloxy- ( 6) and 3-dodecyloxyjatrorrhizine chlorides ( 7) were synthesized and tested for their antimicrobial activity in vitro to evaluate structure-activity relationships. Substitution of the H with alkyl groups at C-3-OH led to significant changes in the antimicrobial activity. The antimicrobial activity of the substituted derivatives was 32 - 1000 times higher than that of jatorrhizine ( 1), which increased as the aliphatic chain was elongated and then decreased slightly when the alkyl chain exceeded eight carbon atoms. 3-Octyloxyjatrorrhizine ( 5) displayed the highest antimicrobial activity of all compounds. The LD (50) values of compounds 1 - 7 were more than 6000 mg/kg body weight, showing a low toxicity. The toxicities of compounds 2 - 7 were slightly lower than that of ( 1).
authors.affiliation: Chemistry Institute of Pharmaceutical resources, School of Pharmaceutical Science, Southwest University, Chongqing, P. R. China.
authors.forename: Li-jun
authors.initials: LJ
authors.lastname: Wang
authors.forename: Xiao-li
authors.initials: XL
authors.lastname: Ye
authors.forename: Xue-gang
authors.initials: XG
authors.lastname: Li
authors.forename: Qing-lei
authors.initials: QL
authors.lastname: Sun
authors.forename: Gang
authors.initials: G
authors.lastname: Yu
authors.forename: Xiao-gang
authors.initials: XG
authors.lastname: Cao
authors.forename: Yan-ting
authors.initials: YT
authors.lastname: Liang
authors.forename: Hua-san
authors.initials: HS
authors.lastname: Zhang
authors.forename: Jia-zhou
authors.initials: JZ
authors.lastname: Zhou
mesh_terms: D000890:Anti-Infective Agents / Q000032:analysis*; D001599:Berberine / Q000031:analogs & derivatives* / Q000032:analysis; D039323:Coptis / Q000737:chemistry; D004365:Drugs, Chinese Herbal / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D018675:Toxicity Tests
chemical_list: D000890:Anti-Infective Agents; D004365:Drugs, Chinese Herbal; C055785:jatrorrhizine; D001599:Berberine