Efficient syntheses, crystal structure, thermal and biological evaluation of amlodipine 4-chlorobenzoyl, 4-chlorobenzene and 2,5-dichlorobenzene sulfonamide derivatives

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dc.authoridSahin, Onur/0000-0003-3765-3235
dc.contributor.authorKanwal, Nosheen
dc.contributor.authorKhan, Islam Ullah
dc.contributor.authorHussain, Erum Akbar
dc.contributor.authorFarid, Sidra
dc.contributor.authorSahin, Onur
dc.date.accessioned2025-03-23T19:41:48Z
dc.date.available2025-03-23T19:41:48Z
dc.date.issued2016
dc.departmentSinop Üniversitesi
dc.description.abstractAn efficient synthesis of new A-2, A-3, and A-4 analogues from amlodipine (A-1) has been achieved. All synthesized compounds were investigated by elemental analysis, FTIR, EIMS, and H-1 NMR techniques. Crystal structures of A-2 and A-3 were determined by single crystal X-ray diffraction method. Compound A-2 crystallizes in a monoclinic space group C2/c having unit cell parameters alpha = 23.8754(9) angstrom, b = 8.6725(3) angstrom, c = 30.5777(12) angstrom, beta = 90.673(2)degrees, and V = 6331.0(4) angstrom(3), whereas A-3 crystallizes in a triclinic space group P (1) over bar having unit cell parameters a = 8.2968(3) angstrom, b = 9.3112(4) angstrom, c = 18.1359(7) angstrom, alpha = 100.692(2)degrees, beta = 98.316(3)degrees, gamma = 102.747(2)degrees, and V = 1317.39(9) angstrom(3). These compounds showed that C-H center dot center dot center dot 0 and N-H center dot center dot center dot O hydrogen bonds stabilize the crystal packing. The results of thermal analysis of all products were consistent with the proposed stoichiometry and compounds were found thermally stable up to 200 degrees C. The compounds were tested for direct free radical scavenging effect toward alpha, alpha-Dipheny1-1-picryl hydrazide (DPPH center dot) and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS center dot+) radical cation in aqueous phosphate-buffered saline of pH 7.4 and showed significant in vitro antioxidant potential. Antiurease activity was also performed; A-2 and A-4 showed excellent results with dose independency. (C) 2016 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
dc.description.sponsorshipHigher Education Commission of Pakistan
dc.description.sponsorshipWe would like to thank Professor Khalid M. Khan, HEJ Institute of Chemistry, University of Karachi for his kind assistance in 1H NMR and mass spectral measurements, Dr. Faiz-ul-Hasan Nasim, Department of Biotechnology, Islamia University Bahawalpur for antiurease activity measurements. We are also thankful to Mr. Naeem Razzaq (Schazoo Laboratories) for providing working standards of amlodipine. The article has been vetted by Dr. Naeem Lodhi, Department of Chemistry, York University, Canada and Mr. M. Siddique Awan, Assistant Professor of English, GC University Lahore, so as to ascertain language accuracy. We strongly acknowledge the financial support of the Higher Education Commission of Pakistan to undertake this research work under its Indigenous Ph.D. Program (Batch III).
dc.identifier.doi10.1016/j.crci.2016.01.015
dc.identifier.endpage603
dc.identifier.issn1631-0748
dc.identifier.issn1878-1543
dc.identifier.issue5
dc.identifier.scopus2-s2.0-84962560431
dc.identifier.scopusqualityQ3
dc.identifier.startpage594
dc.identifier.urihttps://doi.org/10.1016/j.crci.2016.01.015
dc.identifier.urihttps://hdl.handle.net/11486/6650
dc.identifier.volume19
dc.identifier.wosWOS:000385785100008
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier France-Editions Scientifiques Medicales Elsevier
dc.relation.ispartofComptes Rendus Chimie
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250323
dc.subjectAmlodipine derivatives
dc.subjectSynthesis
dc.subjectCrystal structure
dc.subjectAntioxidant potential
dc.subjectAntiurease activity
dc.titleEfficient syntheses, crystal structure, thermal and biological evaluation of amlodipine 4-chlorobenzoyl, 4-chlorobenzene and 2,5-dichlorobenzene sulfonamide derivatives
dc.typeArticle

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