SBA-Pr-SO۳H catalyzed synthesis, and molecular docking study of aryltetrahydrodipyrazolopyridine derivatives as PDK۱ inhibitors
Publish place: Organic Chemistry Research، Vol: 8، Issue: 1
Publish Year: 1401
نوع سند: مقاله ژورنالی
زبان: English
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شناسه ملی سند علمی:
JR_ORGC-8-1_008
تاریخ نمایه سازی: 29 اردیبهشت 1403
Abstract:
Hantzsch reaction is a popular procedure for the synthesis of dihydropyridines (DHPs) through the reaction of two equivalents of a β-ketoester with one equivalent of aldehyde in the presence of an ammonia source. The Hantzsch reaction of pyrazolone, aromatic aldehydes and ammonium acetate was studied in the presence of SBA-Pr-SO۳H, as the catalyst, to gain tetrahydrodipyrazolopyridines. The high yield of products (۸۰-۹۵%) within a short reaction time (۶-۱۵ min) proves the efficiency of this methodology. Finally, molecular docking studies were used to show the binding mode of these compounds in the active site of ۳-phosphoinositide-dependent kinase ۱ (۵OOT). Docking computations show the Gold Score value and the binding mode of resulting complexes. The synthesized compounds can bind to the receptor’s residues by forming hydrogen bonds and π interactions. The detailed analysis of the binding mode of the best-docked molecule exhibited a hydrogen bond between NH substituent and Tyr۲۰. Moreover, π-π and π-cation interactions can be seen with the residues Tyr۲۰ and Lys۳۸, respectively.
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Authors
Ghodsi Mohammadi Ziarani
Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Tehran, Iran
Fatemeh Saidian
Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Tehran, Iran
Parisa Gholamzadeh
Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Tehran, Iran
Jahan B. Ghasemi
School of Chemistry, College of Science, University of Tehran, Tehran, Iran
Elham Aghaee
School of Chemistry, College of Science, University of Tehran, Tehran, Iran
Alireza Badiei
School of Chemistry, College of Science, University of Tehran, Tehran, Iran