Synthesis and antibacterial evaluation of hamacanthin B analogues.
Hamacanthins are a class of antibacterial bisindole alkaloids isolated from marine sponges. Based on structure-activity relationships and in silico MRSA PK binding analysis of these bisindole alkaloids, the authors designed new hamacanthin B derivatives and evaluated their antibacterial activities against drug-resistant pathogens. Racemates of the synthetic products were resolved into their enantiomers by chiral separation using a cellulose column, and antibacterial activities were compared. Unsaturation of the central heterocyclic ring structure and bromine substitution at the indole moiety were found to enhance the antibacterial activities of hamacanthin B analogues.
College of Pharmacy, Pusan National University, Busan 609-735, Republic of Korea.
Ahhyun
A
Kim
College of Pharmacy, Pusan National University, Busan 609-735, Republic of Korea.
Min Jeong
MJ
Kim
College of Pharmacy, Pusan National University, Busan 609-735, Republic of Korea.
Tae Hwan
TH
Noh
College of Pharmacy, Kyung Hee University, Seoul 130-701, Republic of Korea.
Jongki
J
Hong
South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510-650, PR China.
Yonghong
Y
Liu
South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510-650, PR China.
Xiaoyi
X
Wei
College of Pharmacy, Pusan National University, Busan 609-735, Republic of Korea. Electronic address: jhjung@pusan.ac.kr.
Jee H
JH
Jung
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D013293:Enterococcus faecalis / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D066244:Proton Magnetic Resonance Spectroscopy; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D026121:Indole Alkaloids; D011719:Pyrazines; C091314:hamacanthine B
Bisindole alkaloids; Chiral separation; Hamacanthin B; MRSA pyruvate kinase