Synthesis and Antifungal Activity of Some Novel (E)-2, 3-Dihydro-3- [(phenylamino) methylene]-4H-1-benzothiopyran-4-ones

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.

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