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2-(1-吲哚基)喹唑啉-4(3H)-酮衍生物的合成与生物评价。

The Synthesis and Biological Evaluation of 2-(1-Indol-3-yl)quinazolin-4(3)-One Derivatives.

机构信息

Department of Chemistry, Perm State University, Bukireva St. 15, 614990 Perm, Russia.

Institute of Ecology and Genetics of Microorganisms, Ural Branch of the Russian Academy of Sciences, Goleva St. 13, 614081 Perm, Russia.

出版信息

Molecules. 2023 Jul 11;28(14):5348. doi: 10.3390/molecules28145348.

DOI:10.3390/molecules28145348
PMID:37513221
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10384628/
Abstract

The treatment of many bacterial diseases remains a significant problem due to the increasing antibiotic resistance of their infectious agents. Among others, this is related to , especially methicillin-resistant (MRSA) and . In the present article, we report on antibacterial compounds with activity against both and MRSA. A straightforward approach to 2-(1-indol-3-yl)quinazolin-4(3)-one and their analogues was developed. Their structural and functional relationships were also considered. The antimicrobial activity of the synthesized compounds against HRv, ATCC 25923, MRSA ATCC 43300, ATCC 10231, and their role in the inhibition of the biofilm formation of were reported. 2-(5-Iodo-1-indol-3-yl)quinazolin-4(3)-one () showed a low minimum inhibitory concentration (MIC) of 0.98 μg/mL against MRSA. The synthesized compounds were assessed via molecular docking for their ability to bind long RSH (RelA/SpoT homolog) proteins using mycobacterial and streptococcal (p)ppGpp synthetase structures as models. The cytotoxic activity of some synthesized compounds was studied. Compounds , , , , , and 3 displayed significant antiproliferative activities against all the cancer cell lines tested. Indolylquinazolinones , , and showed a preferential suppression of the growth of rapidly dividing A549 cells compared to slower growing fibroblasts of non-tumor etiology.

摘要

由于其感染因子对抗生素的耐药性不断增加，许多细菌性疾病的治疗仍然是一个重大问题。特别是耐甲氧西林金黄色葡萄球菌（MRSA）和耐万古霉素肠球菌（VRE）。在本文中，我们报告了对两种病原体均具有活性的抗菌化合物。开发了一种针对 2-（1-吲哚-3-基）喹唑啉-4（3）-酮及其类似物的直接方法。还考虑了它们的结构和功能关系。报告了合成化合物对 HRv、ATCC 25923、MRSA ATCC 43300、ATCC 10231 的抗菌活性及其在抑制生物膜形成中的作用。2-（5-碘-1-吲哚-3-基）喹唑啉-4（3）-酮（）对 MRSA 的最低抑菌浓度（MIC）低至 0.98μg/mL。使用分枝杆菌和链球菌（p）ppGpp 合酶结构作为模型，通过分子对接评估了合成化合物结合长 RSH（RelA/SpoT 同源物）蛋白的能力。研究了一些合成化合物的细胞毒性。化合物 、、、、、和 3 对所有测试的癌细胞系均表现出显著的抗增殖活性。吲唑喹唑啉酮 、和 对快速分裂的 A549 细胞的生长表现出优先抑制作用，而对非肿瘤病因的生长较慢的成纤维细胞则没有。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/0b74359b347d/molecules-28-05348-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/50af399be8b5/molecules-28-05348-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/49cc8ec4c753/molecules-28-05348-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/43b2ab33e30b/molecules-28-05348-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/39581bbb4e09/molecules-28-05348-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/79b92c767cbe/molecules-28-05348-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/537b3adaf388/molecules-28-05348-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/9bd6e2cbe0c3/molecules-28-05348-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/8d2f56a1c938/molecules-28-05348-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/0b74359b347d/molecules-28-05348-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/50af399be8b5/molecules-28-05348-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/49cc8ec4c753/molecules-28-05348-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/43b2ab33e30b/molecules-28-05348-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/39581bbb4e09/molecules-28-05348-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/79b92c767cbe/molecules-28-05348-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/537b3adaf388/molecules-28-05348-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/9bd6e2cbe0c3/molecules-28-05348-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/8d2f56a1c938/molecules-28-05348-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/228c/10384628/0b74359b347d/molecules-28-05348-g005.jpg

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