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Semi-Synthesis of N-Aryl Amide Analogs of Piperine from Piper nigrum and Evaluation of Their Antitrypanosomal, Antimalarial, and Anti-SARS-CoV-2 Main Protease Activities

التفاصيل البيبلوغرافية
العنوان: Semi-Synthesis of N-Aryl Amide Analogs of Piperine from Piper nigrum and Evaluation of Their Antitrypanosomal, Antimalarial, and Anti-SARS-CoV-2 Main Protease Activities
المؤلفون: Rattanaporn Wansri, Aye Chan Khine Lin, Jutharat Pengon, Sumalee Kamchonwongpaisan, Nitipol Srimongkolpithak, Roonglawan Rattanajak, Patcharin Wilasluck, Peerapon Deetanya, Kittikhun Wangkanont, Kowit Hengphasatporn, Yasuteru Shigeta, Jatupol Liangsakul, Aphinya Suroengrit, Siwaporn Boonyasuppayakorn, Taksina Chuanasa, Wanchai De-eknamkul, Supot Hannongbua, Thanyada Rungrotmongkol, Supakarn Chamni
المصدر: Molecules, Vol 27, Iss 9, p 2841 (2022)
بيانات النشر: MDPI AG, 2022.
سنة النشر: 2022
المجموعة: LCC:Organic chemistry
مصطلحات موضوعية: black pepper, piperine analogs, semi-synthesis, antimalaria, antitrypanosoma, anti-SARS-CoV-2 main protease, Organic chemistry, QD241-441
الوصف: Piper nigrum, or black pepper, produces piperine, an alkaloid that has diverse pharmacological activities. In this study, N-aryl amide piperine analogs were prepared by semi-synthesis involving the saponification of piperine (1) to yield piperic acid (2) followed by esterification to obtain compounds 3, 4, and 5. The compounds were examined for their antitrypanosomal, antimalarial, and anti-SARS-CoV-2 main protease activities. The new 2,5-dimethoxy-substituted phenyl piperamide 5 exhibited the most robust biological activities with no cytotoxicity against mammalian cell lines, Vero and Vero E6, as compared to the other compounds in this series. Its half-maximal inhibitory concentration (IC50) for antitrypanosomal activity against Trypanosoma brucei rhodesiense was 15.46 ± 3.09 μM, and its antimalarial activity against the 3D7 strain of Plasmodium falciparum was 24.55 ± 1.91 μM, which were fourfold and fivefold more potent, respectively, than the activities of piperine. Interestingly, compound 5 inhibited the activity of 3C-like main protease (3CLPro) toward anti-SARS-CoV-2 activity at the IC50 of 106.9 ± 1.2 μM, which was threefold more potent than the activity of rutin. Docking and molecular dynamic simulation indicated that the potential binding of 5 in the 3CLpro active site had the improved binding interaction and stability. Therefore, new aryl amide analogs of piperine 5 should be investigated further as a promising anti-infective agent against human African trypanosomiasis, malaria, and COVID-19.
نوع الوثيقة: article
وصف الملف: electronic resource
اللغة: English
تدمد: 1420-3049
Relation: https://www.mdpi.com/1420-3049/27/9/2841; https://doaj.org/toc/1420-3049
DOI: 10.3390/molecules27092841
URL الوصول: https://doaj.org/article/3c603dafe6ca48c285627729f9f6f080
رقم الانضمام: edsdoj.3c603dafe6ca48c285627729f9f6f080
قاعدة البيانات: Directory of Open Access Journals
الوصف
تدمد:14203049
DOI:10.3390/molecules27092841