Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents.
By introducing various aromatic groups in 13-C of berberine and berberrubine, a series of 13-(substituted benzyl) berberine and berberrubine derivatives were synthesized and examined for antifungal activities against various human pathogenic fungi. The synthesized compounds exhibited more potent antifungal activities than berberine and berberrubine. Among them, 13-(4-isopropyl benzyl) berberine (6e) exerted the most potent antifungal activities against Candida species (MIC=1-8 microg/ml) and a 4-fold stronger activity than 13-(4-isopropyl benzyl) berberrubine (7e) synthesized by pyrolysis of compound 6e.
Park
Ki Duk
KD
Division of Biomaterials Science, Korea Research Institute of Bioscience and Biotechnology, Daejeon 305-333, Republic of Korea.
Lee
Jong Hun
JH
Kim
Sung Han
SH
Kang
Tae Hoon
TH
Moon
Jae Sun
JS
Kim
Sung Uk
SU
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001230:Aspergillus / Q000187:drug effects; D001599:Berberine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects; D003455:Cryptococcus neoformans / Q000187:drug effects; D008826:Microbial Sensitivity Tests
D000935:Antifungal Agents; D001599:Berberine; C115958:berberrubine