بررسی فعالیت ضد تکثیر و ضد اکسیدان هیبریدهای بتا-لاکتام مورفولینو-5،3،1-تریازین

رنجبری, سمیه and بهزادی, مریم and سپهری, ساقی and دادخواه آسمان, مرضیه and جراح پور, علی اصغر and محکم, میلاد and قاسمی, یونس and اکبرزاده, امین رضا and کیان پور, صدیقه and Atioğlu, Zeliha and Özdemir, Namık and Akkurt, Mehmet and نبوی زاده, مسعود and Turos, Edward (1398) بررسی فعالیت ضد تکثیر و ضد اکسیدان هیبریدهای بتا-لاکتام مورفولینو-5،3،1-تریازین. Bioorganic and Medicinal Chemistry ــ . شاپا 0968-0896 (In Press)

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Investigations of Antiproliferative and Antioxidant Activity of β-Lactam Morpholino-1,3,5-Triazine Hybrids

English Abstract

This article reports for the first time the synthesis of some novel β-lactam morpholino-1,3,5- triazine hybrids by a [2+2]-cycloaddition reaction of imines 7a-c, 9a-c and 11 with ketenes derived from substituted acetic acids. The reaction was totally diastereoselective, leading exclusively to the formation of cis-β-lactams 8a-l, 10a-f and 12a-c. The synthesized compounds were tested for activity towards SW1116, MCF-7 and HepG2 cancer cell lines and non-cancerous HEK-293 cell line by MTT assay. None of the compounds exert an observable effect on HepG2, MCF-7 and HEK-293 cells, but compounds 7b, 8f, 8g, 8l, 10c, and 10e exhibited excellent growth inhibitory activity (IC50 < 5 µM) against SW 1116 cells, comparable to that of doxorubicin (IC50 = 6.9 µM). An evaluation of the antioxidant potential of each of the compounds, performed by diphenylpicrylhydrazyl (DPPH) assay, indicated that 7b, 9a, 9b and 9c have strong free radical scavenging activity. UV absorption titration studies reveal that 7b, 8l, 8g and 8f interact strongly 2 with calf-thymus DNA (CT-DNA) in the order of 8l > 7b > 8f > 8g. Collectively, the in vitro capabilities of some of these morpholino-triazine imines and β-lactams suggest possible applications to development of new antioxidants and DNA binding therapeutics.

Item Type:Article
زبان سند : انگلیسی
نویسنده اول :سمیه رنجبری
نویسنده :مریم بهزادی
نویسنده :ساقی سپهری
نویسنده :مرضیه دادخواه آسمان
نویسنده مسئول :علی اصغر جراح پور
نویسنده :میلاد محکم
نویسنده :یونس قاسمی
نویسنده :امین رضا اکبرزاده
نویسنده :صدیقه کیان پور
نویسنده :Zeliha Atioğlu
نویسنده :Namık Özdemir
نویسنده :Mehmet Akkurt
نویسنده :مسعود نبوی زاده
نویسنده :Edward Turos
Additional Information:IF: 2.802 Indexed in: ISI, PubMed/Medline, Scopus, Embase
کلیدواژه ها (انگلیسی):β-lactams, morpholino-1,3,5-triazines, diastereoselective, Staudinger reaction, DNA-binding, antioxidants.
Subjects:QV pharmacology > QV 744 Medicinal Chemistry
Divisions:School of Pharmacy > Department of Medicinal Chemistry
ID Code:12755
Deposited By: ساقی سپهری
Deposited On:21 Dec 1398 08:49
Last Modified:21 Dec 1398 08:49

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