Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold

Xiaobin Wang,Qin Li,Juping Zhang,Xianghui Ruan,Lijuan Chen,Zhuo Chen,Wei Xue,Xinmin Zhong

doi:10.1186/s13065-017-0336-7

Xiaobin Wang, Qin Li

Open Access

https://doi.org/10.1186/s13065-017-0336-7

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Abstract

BackgroundMyricetin and 1,3,4-thiadiazole derivatives were reported to exhibit favorable antiviral and antibacterial activities. Aiming to discover novel myricetin analogues with potent activities, a series of novel myricetin derivatives containing 1,3,4-thiadiazole moiety were synthesized, and their antibacterial and antiviral activities were evaluated.ResultBioassay results indicated that some target compounds exhibited potential antibacterial and antiviral activities. Among them, compounds 2, 3a, 3b, 3d, 3f, 3i, 3m and 3p exhibited excellent antibacterial activities against Xanthomonas oryzae pv. Oryzae (Xoo), with EC50 values of 42.7, 38.6, 20.8, 12.9, 22.7, 27.3, 18.3 and 29.4 μg/mL, respectively, which were better than that of thiadiazole-copper (94.9 μg/mL). Compounds 3b, 3d, 3e, 3f, 3i and 3o showed good antibacterial activities against Ralstonia solanacearum (Rs), with EC50 values of 37.9, 72.6, 43.6, 59.6, 60.6 and 39.6 μg/mL, respectively, which were superior to that of thiadiazole-copper (131.7 μg/mL). In addition, compounds 3d, 3f, 3i and 3m showed better curative activities against tobacco mosaic virus (TMV), with EC50 values of 152.8, 99.7, 127.1, and 167.3 μg/mL, respectively, which were better than that of ningnanmycin (211.1 μg/mL).ConclusionsA series of myricetin derivatives containing 1,3,4-thiadiazole scaffold were synthesized, and their antibacterial activities against Xoo and Rs and their antiviral activity against TMV were evaluated. Bioassays indicated that some target compounds exhibited potential antibacterial and antiviral activities. These results indicated this kind of myricetin analogues could be further studied as potential alternative templates in the search for novel antibacterial and antiviral agents.

Highlights

Myricetin and 1,3,4-thiadiazole derivatives were reported to exhibit favorable antiviral and antibacterial activities
Bioassays indicated that some target compounds exhibited potential antibacterial and antiviral activities
These results indicated this kind of myricetin analogues could be further studied as potential alternative templates in the search for novel antibacterial and antiviral agents

Summary

Introduction

Myricetin and 1,3,4-thiadiazole derivatives were reported to exhibit favorable antiviral and antibacterial activities. Aiming to discover novel myricetin analogues with potent activities, a series of novel myricetin derivatives containing 1,3,4-thiadiazole moiety were synthesized, and their antibacterial and antiviral activities were evaluated. As one of important natural products in medicinal chemistry, myricetin was reported to exhibit extensive bioactivities including antibacterial [7], antiviral [8], anticancer [9], anti-inflammatory [10], antioxidant [11], and hypoglycemic activities [12]. Oryzae (Xoo) and Ralstonia solanacearum (Rs) of myricetin derivatives containing acidamide moiety were recently reported by us [15]. Myricetin derivatives as possible active ingredients play a key role in the searching for novel agrochemicals and pharmaceuticals (Fig. 1)

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