86293-40-5Relevant academic research and scientific papers
Synthesis and in vitro antibacterial activity of quaternized 10-methoxycanthin-6-one derivatives
Li, Na,Liu, Dan,Dai, Jiang-Kun,Wang, Jin-Yi,Wang, Jun-Ru
, (2019/05/02)
Background: Based on our previous work, we found that 10-methoxycanthin-6-one displayed potential antibacterial activity and quaternization was an available method for increasing the antibacterial activity. Here, we explored the antibacterial activity of quaternized 10-methoxy canthin-6-one derivatives. Methods and Results: Twenty-two new 3-N-benzylated 10-methoxy canthin-6-ones were designed and synthesized through quaternization reaction. The in vitro antibacterial activity against three bacteria was evaluated by the double dilution method. Moreover, the structure–activity relationships (SARs) were carefully summarized in order to guide the development of antibacterial canthin-6-one agents. Two highly active compounds (6p and 6t) displayed 8-fold superiority (MIC = 3.91 μg/mL) against agricultural pathogenic bacteria R. solanacearum and P. syringae compared to agrochemical streptomycin sulfate, and showed potential activity against B. cereus. Moreover, these two compounds exhibited good “drug-like” properties, low cytotoxicity, and no inhibition on seed germination. Conclusions: This work provides two new effective quaternized canthin-6-one derivatives as candidate bactericide, promoting the development of natural-sourced bactericides and preservatives.
Design and synthesis of C10 modified and ring-truncated canthin-6-one analogues as effective membrane-active antibacterial agents
Dai, Jiangkun,Dan, Wenjia,Zhang, Yunyun,He, Mengfan,Wang, Junru
supporting information, p. 3123 - 3128 (2018/08/11)
A series of canthin-6-one analogues were designed and synthesized in order to study their antibacterial activity and structure–activity relationships. Compound 22 showed a broad spectrum of antibacterial activity and exhibited better bactericidal effect (
Synthesis and evaluation of ester derivatives of 10-hydroxycanthin-6-one as potential antimicrobial agents
Zhao, Fei,Dai, Jiang-Kun,Liu, Dan,Wang, Shi-Jun,Wang, Jun-Ru
, (2016/04/20)
As part of our continuing research on canthin-6-one antimicrobial agents, a new series of ester derivatives of 10-hydroxycanthin-6-one were synthesized using a simple and effective synthetic route. The structure of each compound was characterized by NMR, ESI-MS, FT-IR, UV, and elemental analysis. The antimicrobial activity of these compounds against three phytopathogenic fungi (Alternaria solani, Fusarium graminearum, and Fusarium solani) and four bacteria (Bacillus cereus, Bacillus subtilis, Ralstonia solanacearum, and Pseudomonas syringae) were evaluated using the mycelium linear growth rate method and micro-broth dilution method, respectively. The structure-activity relationship is discussed. Of the tested compounds, 4 and 7s displayed significant antifungal activity against F. graminearum, with inhibition rates of 100% at a concentration of 50 μg/mL. Compounds 5, 7s, and 7t showed the best inhibitory activity against all the tested bacteria, with minimum inhibitory concentrations (MICs) between 3.91 and 31.25 μg/mL. Thus, 7s emerged as a promising lead compound for the development of novel canthine-6-one antimicrobial agents.
USE OF CANTHIN-6-ONE AND ITS ANALOGS IN THE TREATMENT OF MYCOBACTERIA-LINKED PATHOLOGIES ( amended
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Page/Page column 8, (2011/04/18)
The present invention relates to the use, for the preparation of a medicament intended for the treatment or the prevention of pathologies linked to, or caused by mycobacteria, of at least one of the compounds of the following formula (I): in which B represents in particular a nitrogen atom, and R1, R2, R3, R4, R5, R6, R7 and R8 represent in particular a hydrogen atom.
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities
Soriano-Agaton, Flor,Lagoutte, Delphine,Poupon, Erwan,Roblot, Francois,Fournet, Alain,Gantier, Jean-Charles,Hocquemiller, Reynald
, p. 1581 - 1587 (2008/09/17)
Zanthoxylum chiloperone var. angustifolium was investigated. Alkaloids 1-3 from the canthin-6-one series were characterized. Derivatives 7-28 were prepared by hemisynthesis or total synthesis. All compounds were tested for in vitro antifungal activities against five pathogenic fungal strains. Analogues of canthin-6-one did not show better antifungal activities. 2005 American Chemical Society and American Society of Pharmacognosy.
Selective Oxidation of Canthines to Canthin-6-ones with Triethylbenzylammonium Permanganate
Li, Jia-He,Snyder, John K.
, p. 1485 - 1488 (2007/10/02)
Oxidation of canthines, prepared from intramolecular inverse electron demand Diels-Alder reactions of indole with tethered triazines, produced the corresponding canthin-6-ones regiospecifically, with no detected canthin-4-ones.
