4671-90-3Relevant academic research and scientific papers
Design, synthesis and biological evaluation of novel semicarbazone-selenochroman-4-ones hybrids as potent antifungal agents
Xu, Hang,Su, Xin,Liu, Xiao-qian,Zhang, Kai-peng,Hou, Zhuang,Guo, Chun
supporting information, (2019/10/19)
A series of novel 2,3-dihydro-4H-1-benzoselenin-4-one (thio)semicarbazone derivatives were designed and synthesized by using molecular hybridization approach. All the target compounds were characterized by HRMS and NMR and evaluated in vitro antifungal activity against five pathogenic strains. In comparison with precursor selenochroman-4-ones, the hybrid molecules in this study showed significant improvement in antifungal activities. Notably, compound B8 showed significant antifungal activity against other strains excluding Aspergillus fumigatus (0.25 μg/mL on Candida albicans, 2 μg/mL on Cryptococcus neoformans, 8 μg/mL on Candida zeylanoides and 2 μg/mL on fluconazole-sensitive strains of Candida albicans). Moreover, compounds B8, B9 and C2 also displayed most potent activities against four fluconazole-resistance strains. Especially the MIC values of the hybrid molecule B8 against fluconazole-resistant strains were in the range of 0.5–2 μg/mL. Therefore, the molecular hybridization approach in this study provided new ideas for the development of antifungal drug.
Design, synthesis and antifungal activity of novel selenochroman-4-one derivatives
Xu, Hang,Hu, Yu-Kun,Guo, Meng-Bi,Huang, Ai-Su,Su, Xin,Guo, Chun
, p. 2455 - 2463 (2017/10/06)
A series of novel selenochroman-4-one derivatives bearing semicarbazone or nitrogen heterocycle was designed, synthesized, tested antifungal activity and characterized via 1H-NMR, 13C-NMR, and HRMS. The design of the compounds is based on the principle of molecule hybrid and bioisosterism. We aimed at attaching semicarbazones or nitrogen heterocycle to the selenochroman-4-one for enhancing antifungal activity. The antifungal activity of target compounds was evaluated using the microdilution broth method in vitro test. Bioassay results indicated that some of the derivatives displayed good fungistatic activity on Candida zeylanoides, Candida albicans, Cryptococcus neoformans, resistant to fluconazole strain 103 (Candida albicans), resistant to fluconazole strain 100 (Candida albicans) and strain SC5314 (Candida albicans). All the compounds exhibit antifungal activities against the tested funguses in different levels, among them, 7 compounds of antifungal activity against several funguses is better than that of the control drug fluconazole. Based on the results, preliminary structure activity relationships (SARs) were summarized to serve as a foundation for further investigation.
Chalcogeno Morita-Baylis-Hillman Reaction of 2-(Methylchalcogeno)phenyl Vinyl Ketones with Aldehydes, Ketones, and α-Dicarbonyl Compounds
Kinoshita, Hironori,Kinoshita, Sayaka,Munechika, Yukari,Iwamura, Tatsunori,Watanabe, Shin-Ichi,Kataoka, Tadashi
, p. 4852 - 4861 (2007/10/03)
Reactions of 2-(methylchalcogeno)phenyl vinyl ketones 1 and 4 with aldehydes 5 were conducted in the presence of BF3·Et 2O. The reaction was quenched by addition of Et3N and gave the Morita-Baylis-Hillman adducts 6-7 in good yields. When the reaction mixture of 1 with 5a was worked up with saturated aqueous NaHCO3, the sulfonium salt 8a was obtained together with 6. Ketones 10, α-diketones, and α-oxo esters 13, which hardly react in the traditional Morita-Baylis-Hillman reaction, similarly reacted with 2-(methylchalcogeno)phenyl vinyl ketones 1 and 4 to give the Morita-Baylis-Hillman adducts 11-12 and 14-15. Selenochromanones 9 and 16 were obtained together with 7 and 15 from reactions of seleno derivative 4, with 5 and 13 as by-products. The formation mechanism for the sulfonium salt syn-trans-8a is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
