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Synthesis, Antioxidant and In-Silico Studies of Potent Urease Inhibitors: N-(4-{[(4-Methoxyphenethyl)-(substituted)amino]sulfonyl}phenyl)acetamides.
Drug Res (Stuttg). 2019 Feb; 69(2):111-120.DR

Abstract

In this study, a new series of sulfonamides derivatives was synthesized and their inhibitory effects on DPPH and jack bean urease were evaluated. The in silico studies were also applied to ascertain the interactions of these molecules with active site of the enzyme. Synthesis was initiated by the nucleophilic substitution reaction of 2-(4-methoxyphenyl)-1-ethanamine (1:) with 4-(acetylamino)benzenesulfonyl chloride (2): in aqueous sodium carbonate at pH 9. Precipitates collected were washed and dried to obtain the parent molecule, N-(4-{[(4-methoxyphenethyl)amino]sulfonyl}phenyl)acetamide (3): . Then, this parent was reacted with different alkyl/aralkyl halides, (4A-M:), using dimethylformamide (DMF) as solvent and LiH as an activator to produce a series of new N-(4-{[(4-methoxyphenethyl)-(substituted)amino]sulfonyl}phenyl)acetamides (5A-M:). All the synthesized compounds were characterized by IR, EI-MS, 1H-NMR, 13C-NMR and CHN analysis data. All of the synthesized compounds showed higher urease inhibitory activity than the standard thiourea. The compound 5 F: exhibited very excellent enzyme inhibitory activity with IC50 value of 0.0171±0.0070 µM relative to standard thiourea having IC50 value of 4.7455±0.0546 µM. Molecular docking studies suggested that ligands have good binding energy values and bind within the active region of taget protein. Chemo-informatics properties were evaluated by computational approaches and it was found that synthesized compounds mostly obeyed the Lipinski' rule.

Authors+Show Affiliations

College of Natural science, Department of Biological Sciences, Kongju National University, Gongju-si, South Korea. Department of Chemistry, Government College University, Lahore, Pakistan.College of Natural science, Department of Biological Sciences, Kongju National University, Gongju-si, South Korea.Department of Chemistry, Government College University, Lahore, Pakistan.Department of Chemistry, Government College University, Lahore, Pakistan.Department of Chemistry, Government College University, Lahore, Pakistan.Department of Chemistry, Government College University, Lahore, Pakistan.Faculty of Pharmacyn and Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA, Puncak Alam Campus, Selangor Darul Ehsan, Malaysia.College of Natural science, Department of Biological Sciences, Kongju National University, Gongju-si, South Korea.College of Natural science, Department of Biological Sciences, Kongju National University, Gongju-si, South Korea.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30086567

Citation

Abbasi, Muhammad Athar, et al. "Synthesis, Antioxidant and In-Silico Studies of Potent Urease Inhibitors: N-(4-{[(4-Methoxyphenethyl)-(substituted)amino]sulfonyl}phenyl)acetamides." Drug Research, vol. 69, no. 2, 2019, pp. 111-120.
Abbasi MA, Raza H, Rehman AU, et al. Synthesis, Antioxidant and In-Silico Studies of Potent Urease Inhibitors: N-(4-{[(4-Methoxyphenethyl)-(substituted)amino]sulfonyl}phenyl)acetamides. Drug Res (Stuttg). 2019;69(2):111-120.
Abbasi, M. A., Raza, H., Rehman, A. U., Siddiqui, S. Z., Nazir, M., Mumtaz, A., Shah, S. A. A., Seo, S. Y., & Hassan, M. (2019). Synthesis, Antioxidant and In-Silico Studies of Potent Urease Inhibitors: N-(4-{[(4-Methoxyphenethyl)-(substituted)amino]sulfonyl}phenyl)acetamides. Drug Research, 69(2), 111-120. https://doi.org/10.1055/a-0654-5074
Abbasi MA, et al. Synthesis, Antioxidant and In-Silico Studies of Potent Urease Inhibitors: N-(4-{[(4-Methoxyphenethyl)-(substituted)amino]sulfonyl}phenyl)acetamides. Drug Res (Stuttg). 2019;69(2):111-120. PubMed PMID: 30086567.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis, Antioxidant and In-Silico Studies of Potent Urease Inhibitors: N-(4-{[(4-Methoxyphenethyl)-(substituted)amino]sulfonyl}phenyl)acetamides. AU - Abbasi,Muhammad Athar, AU - Raza,Hussain, AU - Rehman,Aziz Ur, AU - Siddiqui,Sahahat Zahra, AU - Nazir,Majid, AU - Mumtaz,Ayesha, AU - Shah,Syed Adnan Ali, AU - Seo,Sung-Yum, AU - Hassan,Mubashir, Y1 - 2018/08/07/ PY - 2018/8/8/pubmed PY - 2019/6/7/medline PY - 2018/8/8/entrez SP - 111 EP - 120 JF - Drug research JO - Drug Res (Stuttg) VL - 69 IS - 2 N2 - In this study, a new series of sulfonamides derivatives was synthesized and their inhibitory effects on DPPH and jack bean urease were evaluated. The in silico studies were also applied to ascertain the interactions of these molecules with active site of the enzyme. Synthesis was initiated by the nucleophilic substitution reaction of 2-(4-methoxyphenyl)-1-ethanamine (1:) with 4-(acetylamino)benzenesulfonyl chloride (2): in aqueous sodium carbonate at pH 9. Precipitates collected were washed and dried to obtain the parent molecule, N-(4-{[(4-methoxyphenethyl)amino]sulfonyl}phenyl)acetamide (3): . Then, this parent was reacted with different alkyl/aralkyl halides, (4A-M:), using dimethylformamide (DMF) as solvent and LiH as an activator to produce a series of new N-(4-{[(4-methoxyphenethyl)-(substituted)amino]sulfonyl}phenyl)acetamides (5A-M:). All the synthesized compounds were characterized by IR, EI-MS, 1H-NMR, 13C-NMR and CHN analysis data. All of the synthesized compounds showed higher urease inhibitory activity than the standard thiourea. The compound 5 F: exhibited very excellent enzyme inhibitory activity with IC50 value of 0.0171±0.0070 µM relative to standard thiourea having IC50 value of 4.7455±0.0546 µM. Molecular docking studies suggested that ligands have good binding energy values and bind within the active region of taget protein. Chemo-informatics properties were evaluated by computational approaches and it was found that synthesized compounds mostly obeyed the Lipinski' rule. SN - 2194-9387 UR - https://www.unboundmedicine.com/medline/citation/30086567/Synthesis_Antioxidant_and_In_Silico_Studies_of_Potent_Urease_Inhibitors:_N__4_{[_4_Methoxyphenethyl___substituted_amino]sulfonyl}phenyl_acetamides_ L2 - http://www.thieme-connect.com/DOI/DOI?10.1055/a-0654-5074 DB - PRIME DP - Unbound Medicine ER -