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源自S-取代二硫代氨基甲酸盐的对映体席夫碱的合成、表征及抗登革热活性评估

Synthesis, characterization and evaluation of antidengue activity of enantiomeric Schiff bases derived from S-substituted dithiocarbazate.

作者信息

Maryam Maqsood, Tan Sang Loon, Crouse Karen Ann, Mohamed Tahir Mohamed Ibrahim, Chee Hui-Yee

机构信息

Faculty of Natural Sciences, Sardar Bahadur Khan Women University, Balochistan, Quetta Pakistan.

Department of Medical Microbiology and Parasitology, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, SerdangSelangor Malaysia.

出版信息

Turk J Chem. 2020 Oct 26;44(5):1395-1409. doi: 10.3906/kim-2006-22. eCollection 2020.

DOI:10.3906/kim-2006-22
PMID:33488239
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7751940/
Abstract

A series of Schiff bases have been successfully synthesized through the acid-catalyzed condensation of S-substituted dithiocarbazates and three enantiomerically pure monoterpenes, (1 )-(+)-camphor, (1 )-(-)-camphor, (1 )-(-)-camphorquinone, (1 )-(+)-camphorquinone, ( )-(-)-carvone and ( )-(+)-carvone. Spectroscopic results revealed that the Schiff bases containing camphor or carvone likely adopted an -configuration along the characteristic imine bond while those containing camphorquinone assumed a -configuration. The antidengue potential of these compounds was evaluated based on DENV 2 caused cytopathic effect (CPE) reduction-based in vitro evaluation. The compounds were validated through secondary foci forming unit reduction assay (FFURA). Compounds were also tested for their cytotoxicity against Vero cells. The compounds showed variable degrees of antiviral activity with the camphor compounds displaying the highest antidengue potential. The enantiomers of the compounds behaved almost similarly during the antiviral evaluation.

摘要

通过酸催化S-取代二硫代氨基甲酸盐与三种对映体纯的单萜((1 )-(+)-樟脑、(1 )-(-)-樟脑、(1 )-(-)-樟脑醌、(1 )-(+)-樟脑醌、( )-(-)-香芹酮和( )-(+)-香芹酮)缩合,成功合成了一系列席夫碱。光谱结果表明,含有樟脑或香芹酮的席夫碱沿特征亚胺键可能采取 -构型,而含有樟脑醌的席夫碱则采取 -构型。基于登革病毒2引起的细胞病变效应(CPE)降低的体外评估,对这些化合物的抗登革热潜力进行了评估。通过二级病灶形成单位减少试验(FFURA)对这些化合物进行了验证。还测试了这些化合物对Vero细胞的细胞毒性。这些化合物表现出不同程度的抗病毒活性,其中樟脑化合物显示出最高的抗登革热潜力。在抗病毒评估过程中,这些化合物的对映体表现几乎相似。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/70da14f8e75a/turkjchem-44-1395-fig004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/d420c3e734bd/turkjchem-44-1395-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/5418a56dcff2/turkjchem-44-1395-fig001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/4bf295c9fb30/turkjchem-44-1395-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/5f4e4bc24181/turkjchem-44-1395-fig002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/4c824967a36b/turkjchem-44-1395-fig003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/70da14f8e75a/turkjchem-44-1395-fig004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/d420c3e734bd/turkjchem-44-1395-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/5418a56dcff2/turkjchem-44-1395-fig001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/4bf295c9fb30/turkjchem-44-1395-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/5f4e4bc24181/turkjchem-44-1395-fig002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/4c824967a36b/turkjchem-44-1395-fig003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebc8/7751940/70da14f8e75a/turkjchem-44-1395-fig004.jpg

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