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某些噻唑基-儿茶酚化合物的合成、细胞毒性及抗氧化活性评估

Synthesis, Cytotoxicity and Antioxidant Activity Evaluation of Some Thiazolyl-Catechol Compounds.

作者信息

Cornea Alexandra Cătălina, Marc Gabriel, Ionuț Ioana, Moldovan Cristina, Fizeșan Ionel, Petru Andreea-Elena, Creștin Ionuț-Valentin, Pîrnău Adrian, Vlase Laurian, Oniga Ovidiu

机构信息

Department of Pharmaceutical Chemistry, "Iuliu Hațieganu" University of Medicine and Pharmacy, 41 Victor Babeș Street, 400012 Cluj-Napoca, Romania.

Department of Toxicology, Faculty of Pharmacy, "Iuliu Hațieganu" University of Medicine and Pharmacy, 8 Victor Babeș, 400012 Cluj-Napoca, Romania.

出版信息

Antioxidants (Basel). 2024 Aug 1;13(8):937. doi: 10.3390/antiox13080937.

DOI:10.3390/antiox13080937
PMID:39199183
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11351550/
Abstract

A series of thiazolyl-catechol compounds with antioxidant and cytotoxic activities were synthesized by a Hantzsch heterocyclization, using diverse thioamides as the thiocarbonyl component and 4-chloroacetyl-catechol as haloketone. These compounds were characterized by MS, IR spectroscopy, and NMR. Their antioxidant potential was evaluated by antiradical, electron transfer, and ferrous ion chelation assays using ascorbic acid, Trolox, and EDTA-Na as references. The cytotoxicity of the synthesized compounds was evaluated on two different cell types, normal human foreskin fibroblasts (BJ) and human pulmonary malignant cells (A549), using gefitinib as a reference anticancer drug. The results obtained from the tests highlighted compounds and with significant antioxidant activities. The highest cytotoxic potency against A549 cells was exhibited by compounds and , while compound demonstrated exceptional selectivity on malignant cells compared to gefitinib. These promising results encourage further investigation into targeted modifications on position 2 of the thiazole ring, in order to develop novel therapeutic agents.

摘要

通过汉茨希杂环化反应，以不同的硫代酰胺作为硫羰基组分，4-氯乙酰基儿茶酚作为卤代酮，合成了一系列具有抗氧化和细胞毒性活性的噻唑基儿茶酚化合物。这些化合物通过质谱、红外光谱和核磁共振进行表征。以抗坏血酸、Trolox和EDTA-Na为参比，通过抗自由基、电子转移和亚铁离子螯合试验评估了它们的抗氧化潜力。以吉非替尼作为参比抗癌药物，在两种不同的细胞类型，即正常人包皮成纤维细胞（BJ）和人肺恶性细胞（A549）上评估了合成化合物的细胞毒性。试验结果突出显示了化合物 和 具有显著的抗氧化活性。化合物 和 对A549细胞表现出最高的细胞毒性效力，而与吉非替尼相比，化合物 对恶性细胞表现出特殊的选择性。这些有前景的结果促使人们进一步研究噻唑环2位的靶向修饰，以开发新型治疗剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/d2563136dd33/antioxidants-13-00937-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/7f2acd191739/antioxidants-13-00937-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/8c04249acad2/antioxidants-13-00937-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/572b2080e75b/antioxidants-13-00937-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/9f49a181594b/antioxidants-13-00937-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/df55ef9cb161/antioxidants-13-00937-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/d2563136dd33/antioxidants-13-00937-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/7f2acd191739/antioxidants-13-00937-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/8c04249acad2/antioxidants-13-00937-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/572b2080e75b/antioxidants-13-00937-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/9f49a181594b/antioxidants-13-00937-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/df55ef9cb161/antioxidants-13-00937-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b3f/11351550/d2563136dd33/antioxidants-13-00937-g005.jpg

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