Abstract
A series of novel (E)-2,3-dihydro-3-[(phenylamino)methylene]-4H-1-benzothiopyran-4-ones has been synthesized by using 2,3-dihydro-4H-1-benzothiopyran-4-ones as the starting material. The structures of the new compounds are characterized by UV-vis, IR, HRMS, 1H NMR, and 13C NMR. 2D NMR spectroscopic studies revealed that at room temperature, these compounds rather exist in the keto-enamine than in the Schiff base form. The synthesized compounds were evaluated against two species of fungi in vitro by agar double dilution method. The results of antifungal screening revealed that the MIC value of (E)-8-chloro-2,3-dihydro-3-[(4-nitrophenylamino)methylene]-4H-1-benzothiopyran-4-one (4j) against Candida albicans is 32 μg·ml-1 while the control Fluconazole is 64 μg·ml-1.
Keywords: Antifungal activity, benzothiopyran-4-one, enaminones, NMR, synthesis, thiochromanone
Letters in Organic Chemistry
Title:Synthesis and Antifungal Activity of Some Novel (E)-2, 3-Dihydro-3- [(phenylamino) methylene]-4H-1-benzothiopyran-4-ones
Volume: 10 Issue: 3
Author(s): Liu Xiao-Ming, Yang Geng-Liang, Song Ya-Li, Liu Jie-Jie, Wang Yang and Zhang Dong- Nuan
Affiliation:
Keywords: Antifungal activity, benzothiopyran-4-one, enaminones, NMR, synthesis, thiochromanone
Abstract: A series of novel (E)-2,3-dihydro-3-[(phenylamino)methylene]-4H-1-benzothiopyran-4-ones has been synthesized by using 2,3-dihydro-4H-1-benzothiopyran-4-ones as the starting material. The structures of the new compounds are characterized by UV-vis, IR, HRMS, 1H NMR, and 13C NMR. 2D NMR spectroscopic studies revealed that at room temperature, these compounds rather exist in the keto-enamine than in the Schiff base form. The synthesized compounds were evaluated against two species of fungi in vitro by agar double dilution method. The results of antifungal screening revealed that the MIC value of (E)-8-chloro-2,3-dihydro-3-[(4-nitrophenylamino)methylene]-4H-1-benzothiopyran-4-one (4j) against Candida albicans is 32 μg·ml-1 while the control Fluconazole is 64 μg·ml-1.
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Cite this article as:
Xiao-Ming Liu, Geng-Liang Yang, Ya-Li Song, Jie-Jie Liu, Yang Wang and Dong- Nuan Zhang, Synthesis and Antifungal Activity of Some Novel (E)-2, 3-Dihydro-3- [(phenylamino) methylene]-4H-1-benzothiopyran-4-ones, Letters in Organic Chemistry 2013; 10 (3) . https://dx.doi.org/10.2174/1570178611310030016
DOI https://dx.doi.org/10.2174/1570178611310030016 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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