Add time:09/05/2019         Source:sciencedirect.com

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 1H 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 a = 23.8754(9) Å, b = 8.6725(3) Å, c = 30.5777(12) Å, β = 90.673(2)°, and V = 6331.0(4) Å3, whereas A-3 crystallizes in a triclinic space group P1¯ having unit cell parameters a = 8.2968(3) Å, b = 9.3112(4) Å, c = 18.1359(7) Å, α = 100.692(2)°, β = 98.316(3)°, γ = 102.747(2)°, and V = 1317.39(9) Å3. These compounds showed that C–H⋯O and N–H⋯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 °C. The compounds were tested for direct free radical scavenging effect toward α, α-Diphenyl-1-picryl hydrazide (DPPH•) and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) 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.

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