Management of Female Hypospadias

Synthesis of amide derivatives containing the imidazole moiety and evaluation of their anti‐cardiac fibrosis activity

“…To investigate the effect of substituents on the side chain on the inhibitory activity of ALK5, N ‐(2‐oxoethyl) amides ( 13a – x ) were synthesized as shown in Scheme 2. Some of the commercially available requisite aldehydes ( 13b, 13f, 13j, 13l, 13m, 13t, 13u, 13v , and 13w ) are used directly, and the commercially unavailable aldehydes such as N ‐(2‐oxoethyl)butyramide ( 13a ), [ 37,38 ] N ‐(2‐oxoethyl)cyclohexanecarboxamide ( 13c ), [ 37 ] 3‐methyl‐ N ‐(2‐oxoethyl)but‐2‐enamide ( 13d ), [ 39 ] N ‐(2‐oxoethyl)benzamide ( 13e ), [ 37 ] 4‐fluoro‐ N ‐(2‐oxoethyl)benzamide ( 13g ), [ 40 ] 4‐chloro‐ N ‐(2‐oxoethyl)benzamide ( 13h ), [ 41 ] 4‐bromo‐ N ‐(2‐oxoethyl)benzamide ( 13i ), [ 37 ] 4‐methyl‐ N ‐(2‐oxoethyl)benzamide ( 13k ), [ 37 ] N ‐(2‐oxoethyl)‐2‐phenylacetamide ( 13n ), [ 42 ] N ‐(2‐oxoethyl)‐3‐phenylpropanamide ( 13o ), [ 43 ] 2‐(benzyloxy)‐ N ‐(2‐oxoethyl)acetamide ( 13p ), [ 44 ] N ‐(2‐oxoethyl)‐2‐naphthamide ( 13q ), [ 45 ] N ‐(2‐oxoethyl)‐2,2‐diphenylacetamide ( 13r ), [ 46 ] N ‐(2‐oxoethyl)furan‐2‐carboxamide ( 13s ), [ 37 ] and N ‐(2‐oxoethyl)‐2‐(thiophen‐2‐yl)acetamide ( 13x ) [ 47 ] were synthesized according to the known procedures in the literatures. Aminoacetaldehyde dimethyl acetal ( 11 ) was coupled with the appropriate acid chlorides in the presence of triethylamine (TEA) in dichloromethane to give N ‐(2,2‐dimethoxyethyl)acetamides ( 12a – x ) in 51%–95% yields.…”