6790-21-2Relevant academic research and scientific papers
ANTIBACTERIAL AGENTS AGAINST DRUG-RESISTANT STAPHYLOCOCCUS AUREUS OR VANCOMYCIN-RESISTANT ENTEROCOCCUS AND ANTIFUNGAL AGENTS COMPRISING STEPHANITIS SVENSONI-DERIVED POLYKETIDE OR SYNTHETIC ANALOGS THEREOF
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Paragraph 0043; 0045-0042, (2020/10/27)
PROBLEM TO BE SOLVED: To provide antibacterial or antifungal agents comprising a naturally occurring substance or synthetic analogs thereof having high antibacterial activity against methicillin-resistant Staphylococcus aureus or vancomycin-resistant Ente
Structural optimization and antibacterial evaluation of rhodomyrtosone B analogues against MRSA strains
Zhao, Liyun,Liu, Hongxin,Huo, Luqiong,Wang, Miaomiao,Yang, Bao,Zhang, Weimin,Xu, Zhifang,Tan, Haibo,Qiu, Sheng-Xiang
supporting information, p. 1698 - 1707 (2018/10/26)
Methicillin-resistant Staphylococcus aureus (MRSA) infections are well-known as a significant global health challenge. In this study, twenty-two congeners of the natural antibiotic rhodomyrtosone B (RDSB) were synthesized with the aim of specifically enhancing the structural diversity through modifying the pendant acyl moiety. The structure-activity relationship study against various MRSA strains revealed that a suitable hydrophobic acyl tail in the phloroglucinol scaffold is a prerequisite for antibacterial activity. Notably, RDSB analogue 11k was identified as a promising lead compound with significant in vitro and in vivo antibacterial activities against a panel of hospital mortality-relevant MRSA strains. Moreover, compound 11k possessed other potent advantages, including breadth of the antibacterial spectrum, rapidity of bactericidal action, and excellent membrane selectivity. The mode of action study of compound 11k at the biophysical and morphology levels disclosed that 11k exerted its MRSA bactericidal action by membrane superpolarization resulting in cell lysis and membrane disruption. Collectively, the presented results indicate that the novel modified RDSB analogue 11k warrants further exploration as a promising candidate for the treatment of MRSA infections.
Structure-activity relationships and optimization of acyclic acylphloroglucinol analogues as novel antimicrobial agents
Tan, Haibo,Liu, Hongxin,Zhao, Liyun,Yuan, Yao,Li, Bailin,Jiang, Yueming,Gong, Liang,Qiu, Shengxiang
supporting information, p. 492 - 499 (2016/10/04)
Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious threat to global public health, because it exhibits resistance to existing antibiotics and therefore high rates of morbidity and mortality. In this study, twenty-one natural product-based acylphloroglucinol congeners were synthesized, which possessed different side chains. Antibacterial screening against MRSA strains revealed that acyl moiety tailoring is a prerequisite for the antibacterial activity. Moreover, the lipophilicity, rather than the magnitude of the hydrophobic acyl tail dominates variability in activity potency. Compound 11j was identified as a promising lead for the generation of new anti-MRSA drug development. It was discovered by optimization of the side chain length in light of the potency, the breadth of the antibacterial spectrum, the rate of bactericidal action, as well as the membrane selectivity. Compound 11j exerted profound in?vitro antibacterial activity against the MRSA strain (JCSC 2172), and its MIC was 3-4 orders of magnitude lower than that of vancomycin. A preliminary mode of action study of compound 11j at the biophysical and morphology levels disclosed that the mechanism underlying its anti-MRSA activity included membrane depolarization and, to a lesser extent, membrane disruption and cell lysis.
Synthesis of novel 3-alkyl-3′,4′,5,7-tetrahydroxyflavones
Seixas, Raquel S. G. R.,Pinto, Diana C. G. A.,Silva, Artur M. S.,Cavaleiro, Jos A. S.
, p. 718 - 724 (2008/12/22)
Novel 3-alkyl-3′,4′,5,7-tetrahydroxyflavones have been prepared. The synthetic strategy involves the preparation of 1-(2-hydroxy-4,6-dimethoxyphenyl)alkan-1-ones from the FriedelCrafts acylation of phloroglucinol followed by methylation. These key compounds were submitted to the three-step BakerVenkataraman method, giving the 3-alkyl-3′,4′, 5,7-tetramethoxyflavones, which were demethylated with boron tribromide. CSIRO 2008.
Simplified YM-26734 inhibitors of secreted phospholipase A2 group IIA
Oslund, Rob C.,Cermak, Nathan,Verlinde, Christophe L.M.J.,Gelb, Michael H.
supporting information; experimental part, p. 5415 - 5419 (2009/05/30)
Simplified analogs of YM-26734, a known inhibitor of secreted phospholipase A2 (sPLA2) group IIA, were synthesized and found to also display potent inhibition at low nanomolar concentrations. Analogs were based on the didodecanoylphl
(+)-Myristinin A, a naturally occurring DNA polymerase β inhibitor and potent DNA-damaging agent
Maloney, David J.,Deng, Jing-Zhen,Starck, Shelley R.,Gao, Zhijie,Hecht, Sidney M.
, p. 4140 - 4141 (2007/10/03)
The first stereoselective total synthesis of the naturally occurring flavan myristinin A has been accomplished, as well as its biochemical evaluation. This synthesis verified the structural assignment and allowed for the determination of the absolute ster
Antifungal Activities of 2,4,6-Trihydroxyacylophenones and Related Compounds
Mizobuchi, Shigeyuki,Sato, Yuko
, p. 719 - 724 (2007/10/02)
The antifungal activities of sixty two 2,4,6-trihydroxyacylophenones and related compounds against Trichophyton spp. and other fungi were investigated to study their structure-activity relationship.It was found that the activities of these compounds were closely related to the length of the acyl and alkyl chains attached to the 1,3,5-trihydroxybenzene moiety.Among the compounds tested, 2,4,6-trihydroxy-3-nonylacetophenone (V-7) showed the highest activity against Trichophyton spp., with MICs being 1.57 μg/ml, and was more active than amphotericin B.
