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Rational Design and Synthesis of 1‐(Arylideneamino)‐4‐aryl‐1 H ‐imidazole‐2‐amine Derivatives as Antiplatelet Agents
Author(s) -
Amidi Salimeh,
Esfahanizadeh Marjan,
Tabib Kimia,
Soleimani Zohreh,
Kobarfard Farzad
Publication year - 2017
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201700123
Subject(s) - chemistry , imidazole , azole , amine gas treating , aryl , stereochemistry , hydrazone , ring (chemistry) , thiophene , medicinal chemistry , organic chemistry , alkyl , antifungal , medicine , dermatology
Based on previous studies indicating the pharmacophoric role of a hydrazone group and azole rings for antiplatelet aggregation activity, a few series of compounds with both hydrazone and an azole (imidazole) ring in their structures were synthesized, and their platelet aggregation inhibitory effects were evaluated. Two of these 1‐(arylideneamino)‐4‐aryl‐1 H ‐imidazole‐2‐amine derivatives, compounds 4 a [( E )‐1‐(benzylideneamino)‐4‐phenyl‐1 H ‐imidazol‐2‐amine] and 4 p [( E )‐4‐phenyl‐1‐((thiophen‐2‐ylmethylene)amino)‐1 H ‐imidazol‐2‐amine], exhibited IC 50 values similar to that of acetylsalicylic acid against collagen as a platelet aggregation inducer. Structural comparison of the synthesized compounds revealed that those with a para ‐substituted phenyl ring on the imidazole were among the most active compounds against platelet aggregation induced by arachidonic acid (AA), and the presence of a thiophene ring in these compounds maximized their antiplatelet activity.