Premium
Synthesis and crystal structures of the potential tyrosinase inhibitors N ‐(4‐acetylphenyl)‐2‐chloroacetamide and 2‐(4‐acetylanilino)‐2‐oxoethyl cinnamate
Author(s) -
Ashraf Zaman,
Kim Daeyoung,
Seo Sung-Yum,
Kang Sung Kwon
Publication year - 2016
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s205322961502433x
Subject(s) - acetamide , amide , chemistry , dihedral angle , tyrosinase , stereochemistry , crystal structure , molecule , benzoic acid , ring (chemistry) , hydrogen bond , enzyme , crystallography , organic chemistry
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, C 10 H 10 ClNO 2 , (I), and 2‐(4‐acetylanilino)‐2‐oxoethyl cinnamate, C 19 H 17 NO 4 , (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.