title: Synthesis and crystal structures of the potential tyrosinase inhibitors N-(4-acetylphenyl)-2-chloroacetamide and 2-(4-acetylanilino)-2-oxoethyl cinnamate.
abstract: Substituted benzoic acid and cinnamic acid esters are of interest as tyrosinase inhibitors and the development of such inhibitors may help in diminishing many dermatological disorders. The tyrosinase enzyme has also been linked to Parkinson's disease. In view of hydroxylated compounds having ester and amide functionalities to potentially inhibit tyrosinase, we herein report the synthesis and crystal structures of two amide-based derivatives, namely N-(4-acetylphenyl)-2-chloroacetamide, C10H10ClNO2, (I), and 2-(4-acetylanilino)-2-oxoethyl cinnamate, C19H17NO4, (II). In compound (I), the acetylphenyl ring and the N-(C=O)-C unit of the acetamide group are almost coplanar, with a dihedral angle of 7.39 (18)°. Instead of esterification, a cheaper and more efficient synthetic method has been developed for the preparation of compound (II). The molecular geometry of compound (II) is a V-shape. The acetamide and cinnamate groups are almost planar, with mean deviations of 0.088 and 0.046 Å, respectively; the dihedral angle between these groups is 77.39 (7)°. The carbonyl O atoms are positioned syn and anti to the amide carbonyl O atom. In the crystals of (I) and (II), N-H...O, C-H...O and C-H...π interactions link the molecules into a three-dimensional network.
authors: Department of Biology, College of Natural Sciences, Kongju National University, Gongju 314-701, Republic of Korea.
authors: Zaman
authors: Z
authors: Ashraf
authors: Department of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea.
authors: Daeyoung
authors: D
authors: Kim
authors: Department of Biology, College of Natural Sciences, Kongju National University, Gongju 314-701, Republic of Korea.
authors: Sung-Yum
authors: SY
authors: Seo
authors: Department of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea.
authors: Sung Kwon
authors: SK
authors: Kang
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D002934:Cinnamates / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000737:chemistry* / Q000378:metabolism
chemical_list: C000608658:2-(4-acetylanilino)-2-oxoethyl cinnamate; D000081:Acetamides; D002934:Cinnamates; D004791:Enzyme Inhibitors; C000608657:N-(4-acetylphenyl)-2-chloroacetamide; D014442:Monophenol Monooxygenase
keywords: acetamide; cinnamate ester; crystal structure; hydrogen bonding; tyrosinase inhibitor