Efficient syntheses, crystal structure, thermal and biological evaluation of amlodipine 4-chlorobenzoyl, 4-chlorobenzene and 2,5-dichlorobenzene sulfonamide derivatives
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Tarih
2016
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Elsevier France-Editions Scientifiques Medicales Elsevier
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
An 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.
Açıklama
Anahtar Kelimeler
Amlodipine derivatives, Synthesis, Crystal structure, Antioxidant potential, Antiurease activity
Kaynak
Comptes Rendus Chimie
WoS Q Değeri
Q3
Scopus Q Değeri
Q3
Cilt
19
Sayı
5
