Synthesis, biological and molecular modelling for 1,3,4-thiadiazole sulfonyl thioureas: bacterial and fungal activity

Dinh Thanh, Nguyen; Ngoc Toan, Vu; Thi Kim Giang, Nguyen; Thi Kim Van, Hoang; Son Hai, Do; Minh Tri, Nguyen; Ngoc Toan, Duong

doi:10.1039/d3md00508a

RSC Med. Chem.

2023

DOI: 10.1039/d3md00508a

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Synthesis, biological and molecular modelling for 1,3,4-thiadiazole sulfonyl thioureas: bacterial and fungal activity

Nguyen Dinh Thanh,

Vu Ngoc Toan,

Nguyen Thi Kim Giang

et al.

Abstract: Some substituted thioureas 6a-i containing 1,3,4-thiadiazole ring were synthesized by reaction of corresponding different substituted 2-amino-1,3,4-thiadiazoles 3a-i with p-toluenesulfonyl isocyanate in one-pot procedure. The antibacterial as well as antifungal activities...

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Pinonic Acid Derivatives Containing Thiourea Motif: Promising Antifungal Lead Compound Targeting Cellular Barrier of Colletotrichum fructicola

Wang,

Duan,

et al. 2024

J. Agric. Food Chem.

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In order to explore novel antifungal lead compounds from plant essential oil, thirty-two pinonic acid derivatives containing thiourea groups were designed and synthesized using α-pinene as a raw material. One of these pinonic acid derivatives compound 3a exhibited noteworthy in vitro antifungal activity against Colletotrichum fructicola (EC 50 = 9.22 mg/L), which was comparable to that of the positive control kresoxim-methyl (EC 50 = 9.69 mg/L). Structure−activity relationship (SAR) studies demonstrated that the introduction of thiourea groups, F atoms, and Cl atoms into the structure of pinonic acid derivatives significantly improved their antifungal activity. The in vivo antifungal test revealed that compound 3a could effectively control pear anthracnose. It also proved that compound 3a showed low acute oral toxicity to honeybees (LD 50 > 100 μg/bee) and low or no cytotoxicity to LO2 and HEK293 cell lines. The preliminary mechanism of action studies revealed that compound 3a caused mycelium deformity, increased cell membrane permeability, blocked the normal process of phospholipase C on the cell membrane, and reduced mycelium protein content. The results of molecular docking studies demonstrated the stable binding of compound 3a to phospholipase C and chitin synthetase. This study suggested that compound 3a could be used as a promising lead compound for the development of novel antifungal agents targeting the cellular barrier of C. fructicola.

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Pinonic Acid Derivatives Containing Thiourea Motif: Promising Antifungal Lead Compound Targeting Cellular Barrier of Colletotrichum fructicola

Wang,

Duan,

et al. 2024

J. Agric. Food Chem.

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Synthesis and biological evaluation of new naphthalimide–thiourea derivatives as potent antimicrobial agents active against multidrug-resistant Staphylococcus aureus and Mycobacterium tuberculosis

Rana,

Parupalli,

Akhir

et al. 2024

RSC Med. Chem.

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Synthesis, biological and molecular modelling for 1,3,4-thiadiazole sulfonyl thioureas: bacterial and fungal activity

Abstract: Some substituted thioureas 6a-i containing 1,3,4-thiadiazole ring were synthesized by reaction of corresponding different substituted 2-amino-1,3,4-thiadiazoles 3a-i with p-toluenesulfonyl isocyanate in one-pot procedure. The antibacterial as well as antifungal activities...

Cited by 2 publications

References 55 publications

Pinonic Acid Derivatives Containing Thiourea Motif: Promising Antifungal Lead Compound Targeting Cellular Barrier of Colletotrichum fructicola

Pinonic Acid Derivatives Containing Thiourea Motif: Promising Antifungal Lead Compound Targeting Cellular Barrier of Colletotrichum fructicola

Synthesis and biological evaluation of new naphthalimide–thiourea derivatives as potent antimicrobial agents active against multidrug-resistant Staphylococcus aureus and Mycobacterium tuberculosis

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