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通过重新设计多组分方法合成新型含二硫代氨基甲酸盐的哌嗪衍生物用于抗菌和抗真菌

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

作者信息

Halimehjani Azim Ziyaei, Dehghan Faezeh, Tafakori Vida, Amini Elaheh, Hooshmand Seyyed Emad, Nosood Yazdanbkhsh Lotfi

机构信息

Faculty of Chemistry, Kharazmi University, 49 Mofateh St., 15719-14911, Tehran, Iran.

Department of Cell and Molecular Biology, Faculty of Biological Sciences, Kharazmi University, Tehran, Iran.

出版信息

Heliyon. 2022 May 30;8(6):e09564. doi: 10.1016/j.heliyon.2022.e09564. eCollection 2022 Jun.

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 the reaction of amines, CS 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.

摘要

通过1,4-二氮杂双环[2.2.2]辛烷(DABCO)环的C-N键裂解,开发了一种无金属多组分合成路线,用于多样地制备含二硫代氨基甲酸盐的哌嗪衍生物。这种多组分重新设计方法使胺、CS和DABCO盐在一锅反应中进行反应。各种DABCO盐和仲胺在该方案中耐受性良好,以良好至高产率得到了广泛的含二硫代氨基甲酸盐的哌嗪。然后,所选择的化合物已被用于对抗一些关键类型的细菌和真菌。通过纸片扩散法和最低抑菌浓度法对细菌(革兰氏阳性和革兰氏阴性)进行研究,一定数量的合成化合物不仅显示出适当的抗菌活性,而且还表现出良好至优异的抗真菌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c033/9163505/cb6eb092d39c/ga1.jpg

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