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Research in Pharmaceutical Sciences، جلد ۱۲، شماره ۵، صفحات ۳۵۳-۳۶۳
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عنوان انگلیسی Facile one-pot four-component synthesis of 3,4-dihydro-2-pyridone derivatives: novel urease inhibitor scaffold
چکیده انگلیسی مقاله In the current study, a series of 3,4-dihydro-2-pyridone derivatives were synthesized in a one-pot four-component reaction of Meldrum’s acid, benzaldehyde derivatives, methyl acetoacetate, and ammonium acetate. SiO 2 -Pr-SO 3 H was used as an efficient catalyst for the synthesis of the target compounds under solvent-free conditions. The most probable mechanism for this reaction has been discussed. The advantages of this methodology are high product yields, being environmentally benign, short reaction times, and easy handling. Eight 2-pyridinone derivatives were evaluated for their inhibitory activities against Jack bean urease. Molecular docking study of the synthesized compounds was also evaluated. All compounds showed good activities against urease and among them, 4-(4-nitrophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridone ( 5a ) showed the most potent activity (IC 50 = 29.12 µM), more potent than hydroxyurea as the reference drug (IC 50 = 100.0 µM). Also, the results from docking studies were in good agreement with those obtained with in vitro assay. According to the docking studies methionine (Met) 637 and nitro phenyl ring cause n-π interaction between lone pair of sulfur atom and π aromatic ring. Moreover, hydrophobic interactions existed between compound 5a and alanine (ALA) 636, ALA 440, and isoleucine 411. The results indicated that the inhibitory activities increased with the increase of electron withdrawing ability of the groups despite a less important role of lipophilicity in increasing the inhibitory activity.
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نویسندگان مقاله آرش مدرس حکیمی | arash modarres hakimi
2school of chemistry, college of science, university of tehran, tehran, i.r. iran.

سازمان اصلی تایید شده: دانشگاه تهران (Tehran university)

نگار لشگری | negar lashgari
1drug design amp; development research centre and department of medicinal chemistry, faculty of pharmacy, tehran university of medical sciences, tehran, i.r. iran.

سازمان اصلی تایید شده: دانشگاه علوم پزشکی تهران (Tehran university of medical sciences)

شبنم mahernia | shabnam mahernia
3department of chemistry, alzahra university, tehran, i.r. iran.

سازمان اصلی تایید شده: دانشگاه الزهرا (Alzahra university)

قدسی محمدی زیارانی | ghodsi mohammadi ziarani
1drug design amp; development research centre and department of medicinal chemistry, faculty of pharmacy, tehran university of medical sciences, tehran, i.r. iran.

سازمان اصلی تایید شده: دانشگاه علوم پزشکی تهران (Tehran university of medical sciences)

مسعود امانلو | massoud amanlou


نشانی اینترنتی http://rps.mui.ac.ir/index.php/jrps/article/view/1780
فایل مقاله اشکال در دسترسی به فایل - ./files/site1/rds_journals/115/article-115-432182.pdf
کد مقاله (doi)
زبان مقاله منتشر شده en
موضوعات مقاله منتشر شده
نوع مقاله منتشر شده Original Article
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