Synthesis, structure and molecular docking analysis of an anticancer drug of N-(2-aminophenyl)-2-(2-isopropylphenoxy) acetamide

Abstract

N-(2-aminophenyl)-2-(2-isopropylphenoxy) acetamide(3) has been synthesized in good yield by stirring compound ethyl 2-(2-isopropylphenoxy) acetic acid(1), with, 2-diaminobenzene (2), in dry dichloromethane followed by the addition of lutidine, and TBTU in cooled condition. The crude product (3) was recrystallized and elucidated by elemental analyses and spectroscopic techniques (HNMR, LC-MS). The anticancer activity was confirmed by in silico modeling study which targets the VEGFr receptor. The compound crystallizes in the orthorhombic crystal system with space group Pbca with unit cell parameters: a = 7.4250 (4) Å, b = 14.9753 (7) Å, c = 27.5656 (14) Å and Z = 4. The crystal structure has been solved by using direct methods and refined by full matrix least-squares procédures to a final R-factor of 0.042 for 2158 observed reflections. The structure exhibits intermolecular H-bonds of the type N–H⋅⋅⋅O. In addition, two intramolecular interactions N1-H1…O2 and N2-H2B…N1 were also observed.