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Synthesis of novel antibacterial and antifungal dithiocarbamate-containing piperazine derivatives via re-engineering multicomponent approach.

ABSTRACT: A metal-free multicomponent synthetic route for the diverse preparation of dithiocarbamate-containing piperazine derivatives was developed through the C-N bond cleavage of DABCO ring. This multicomponent re-engineering approach proceeds via the reaction of amines, CS₂ and DABCO salts in one pot. Various DABCO salts and secondary amines are tolerated well in this protocol to afford a broad spectrum of dithiocarbamate-containing piperazines in good to high yields. Then, the selected compounds have been deployed against some critical types of bacteria and fungi. A certain number of synthesized compounds revealed not only appropriate antibacterial activity as investigated by disc fusion and minimum inhibitory concentration methods against bacteria (Gram-positive and Gram-negative), but also depicted good to excellent antifungal activity.

SUBMITTER: Halimehjani AZ

PROVIDER: S-EPMC9163505 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Synthesis of novel antibacterial and antifungal dithiocarbamate-containing piperazine derivatives via re-engineering multicomponent approach.

Halimehjani Azim Ziyaei AZ Dehghan Faezeh F Tafakori Vida V Amini Elaheh E Hooshmand Seyyed Emad SE Nosood Yazdanbkhsh Lotfi YL

Heliyon 20220530 6

A metal-free multicomponent synthetic route for the diverse preparation of dithiocarbamate-containing piperazine derivatives was developed through the C-N bond cleavage of DABCO ring. This multicomponent re-engineering approach proceeds <i>via</i> the reaction of amines, CS<sub>2</sub> and DABCO salts in one pot. Various DABCO salts and secondary amines are tolerated well in this protocol to afford a broad spectrum of dithiocarbamate-containing piperazines in good to high yields. Then, the selec ...[more]

PMID: 35669544

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Project description:BackgroundPlant fungi (e.g., Pellicularia sasakii, Gibberella zeae, Fusarium oxysporum, and Cytospora mandshurica and Phytophthora infestans) and bacteria (e.g., Ralstonia solanacearum) are extremely difficult to manage in agricultural production. The high incidence of plant mortality and the lack of effective control methods make P. sasakii and R. solanacearum two of the world's most destructive plant pathogens. Pathogenic fungi and bacteria are responsible for billions of dollars in economic losses worldwide each year. Thus, we designed an active amide structure and synthesized a series of novel amide derivatives containing a triazole moiety to discover new bioactive molecules and pesticides that can act against fungi and bacteria.ResultsA series of amide derivatives containing a triazole moiety were synthesized. All the obtained compounds were characterized through proton and carbon nuclear magnetic resonance spectroscopy, infrared spectroscopy, and elemental analysis. Preliminary antifungal activity test showed that some of the synthesized compounds exhibited moderate antifungal activity against P. sasakii, G. azeae, F. oxysporum, C. mandshurica, and P. infestans at 50 mg/L. Compound 4u displayed more potent antifungal activity against P. sasakii and G. azeae than hymexazol. Preliminary antibacterial activity results showed that some of the synthesized compounds exhibited high anti-bacterial activity against R. solanacearum at 200 mg/L. Compounds 4m and 4q displayed high antibacterial activity against R. solanacearum, with 71% and 65% inhibitory rates, respectively.ConclusionsA series of novel amide derivatives containing 1,2,4-triazole moiety were synthesized through the reaction of intermediate 3 with different acyl chlorides and anhydrous potassium carbonates in anhydrous tetrahydrofuran at 50°C, using 2,4-dichloroacetophenoneas as a starting material. The title compounds exhibited high inhibitory effects against P. sasakii, R. solanacearum, and G. azeae.

Dataset Information

Synthesis of novel antibacterial and antifungal dithiocarbamate-containing piperazine derivatives via re-engineering multicomponent approach.

Publications

Synthesis of novel antibacterial and antifungal dithiocarbamate-containing piperazine derivatives via re-engineering multicomponent approach.

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