Synthesis and bioactivity of 1,3-thiazolidine-2-thione derivatives against type III secretion system of Xanthomonas oryzae

Tao, Hui; Tian, Hao; Jiang, Shan; Xiang, Xuwen; Ahmed, Wasim; Tang, Ri‐Yuan; Cui, Zi‐Ning

doi:10.1016/j.bmc.2019.06.019

Cited by 9 publications

(12 citation statements)

References 35 publications

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“…In this study, we extended our previous work − to synthesize a new series of 1,3-thiazole derivatives. We have screened all compounds by using a flow cytometry analysis.…”

Section: Introductionmentioning

confidence: 88%

Novel S-Thiazol-2-yl-furan-2-carbothioate Derivatives as Potential T3SS Inhibitors Against Xanthomonas oryzae on Rice

Jiang

Xiang

et al. 2019

J. Agric. Food Chem.

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Bacterial leaf blight (BLB) caused by Xanthomonas oryzae pv oryzae (Xoo) is considered as the most destructive disease of rice. The use of bactericides is among the most widely used traditional methods to control this destructive disease. The excessive and repeated use of the same bactericides is also becoming the reason behind the development of bactericide resistance. The widely used method for finding the new antimicrobial agents often involves the bacterial virulence factors as a target without affecting bacterial growth. Type III secretion system (T3SS) is a protein appendage and is considered as having essential virulence factors in most Gram-negative bacteria. Due to the conserved construct, T3SS has been regarded as an important mark for the blooming of novel antimicrobial drugs. Toward the search of new T3SS inhibitors, an alternative series of 1,3-thiazole derivatives were designed and synthesized. Their structures were characterized and confirmed by 1 H NMR, 13 C NMR, MS, and elemental analysis. All the title compounds inhibited the promoter activity of hpa1 gene significantly. Eight of them showed better inhibition than our previous T3SS inhibitor TS006 (o-coumaric acid, OCA). The treatment of Xoo with eight compounds significantly attenuated HR without affecting bacterial growth. The mRNA levels of some representative genes (hrp/hrc genes) were reduced up to different extents. In vivo bioassay results showed that eight T3SS inhibitors could reduce bacterial leaf blight and bacterial leaf streak symptoms on rice, significantly.

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“…In this study, we extended our previous work − to synthesize a new series of 1,3-thiazole derivatives. We have screened all compounds by using a flow cytometry analysis.…”

Section: Introductionmentioning

confidence: 88%

Novel S-Thiazol-2-yl-furan-2-carbothioate Derivatives as Potential T3SS Inhibitors Against Xanthomonas oryzae on Rice

Jiang

Xiang

et al. 2019

J. Agric. Food Chem.

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“…X. oryzae pv. Oryzae (Xoo) is one of the main bacteria that causes rice leaf blight [ 118 , 119 ]. Xiang et al [ 120 ] have been working on Xoo T3SS inhibitors ( Figure 8 ).…”

Section: Synthesized Inhibitors Of T3sssmentioning

confidence: 99%

Research Progress on Small Molecular Inhibitors of the Type 3 Secretion System

Liu

Wei

et al. 2022

Molecules

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The overuse of antibiotics has led to severe bacterial drug resistance. Blocking pathogen virulence devices is a highly effective approach to combating bacterial resistance worldwide. Type three secretion systems (T3SSs) are significant virulence factors in Gram-negative pathogens. Inhibition of these systems can effectively weaken infection whilst having no significant effect on bacterial growth. Therefore, T3SS inhibitors may be a powerful weapon against resistance in Gram-negative bacteria, and there has been increasing interest in the research and development of T3SS inhibitors. This review outlines several reported small-molecule inhibitors of the T3SS, covering those of synthetic and natural origin, including their sources, structures, and mechanisms of action.

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“…Among them, some compounds showed higher PKM2 activation activity and also exhibited significant antiproliferative activities on human cancer cell lines (IC 50: furan. [153] The general synthetic route for the compounds is shown in Scheme 38. The key intermediate was synthesized using substituted aniline as the starting material via Meerwein arylation reaction.…”

Section: Thiazolidine Thionesmentioning

confidence: 99%

“…Tao et al designed and synthesized a series of 1,3thiazolidine-2-thione derivatives containing 5-phenyl-2furan. [153] The general synthetic route for the compounds is shown in Scheme 38. The key intermediate was synthesized using substituted aniline as the starting material via Meerwein arylation reaction.…”

Section: Thiazolidine Thionesmentioning

confidence: 99%

Thione Derivatives as Medicinally Important Compounds

2021

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Like nitrogen-containing heterocycles, sulfur-containing heterocyclic compounds also have a lot of significant applications. These sulfur heterocycles are mainly used as a core for the synthesis of different heterocyclic compounds with various biological applications. It also occupies a huge part of natural products. In this review, we focus on the thiones-the analogous of ketones. Syntheses of thiones as well as their applications as biologically active compounds are discussed in great detail. We have considered seven different classes of thiones such as Benzimidazole thiones, Triazole thiones, Pyrimidine thiones, Thiadiazine thiones, Thiazoline thiones, Thiazolidine thiones, and Quinazoline thiones.

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Synthesis and bioactivity of 1,3-thiazolidine-2-thione derivatives against type III secretion system of Xanthomonas oryzae

Cited by 9 publications

References 35 publications

Novel S-Thiazol-2-yl-furan-2-carbothioate Derivatives as Potential T3SS Inhibitors Against Xanthomonas oryzae on Rice

Novel S-Thiazol-2-yl-furan-2-carbothioate Derivatives as Potential T3SS Inhibitors Against Xanthomonas oryzae on Rice

Research Progress on Small Molecular Inhibitors of the Type 3 Secretion System

Thione Derivatives as Medicinally Important Compounds

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