Loading…

Synthesis, biological evaluation and molecular docking studies of novel 2-(2-cyanophenyl)-N-phenylacetamide derivatives

A series of novel 2-(2-cyanophenyl)- N -phenylacetamide derivatives 3(a-u) were designed and synthesized via selective amidation of methyl-2-(2-cyanophenyl)acetates over amidine formation by using AlMe 3 as catalyst in good yields. All the newly synthesized derivatives were well characterized by 1 H...

Full description

Saved in:
Bibliographic Details
Published in:Research on chemical intermediates 2018-09, Vol.44 (9), p.5467-5481
Main Authors: Konidena, Lakshmi Narayana Sharma, Boda, Sathish Kumar, Chettu, Suresh Kumar, Sorra, Kumaraswamy, Enaganti, Sreenivas, Mukkavilli, Praveena, Kameswara Rao, N. S., Anantha Lakshmi, P. V., Korupolu, Raghu Babu
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A series of novel 2-(2-cyanophenyl)- N -phenylacetamide derivatives 3(a-u) were designed and synthesized via selective amidation of methyl-2-(2-cyanophenyl)acetates over amidine formation by using AlMe 3 as catalyst in good yields. All the newly synthesized derivatives were well characterized by 1 H NMR, 13 C NMR, FTIR and HRMS spectral techniques. All the synthesized title compounds were evaluated for their in vitro anticancer activity against three cancer cell lines. Among all compounds, 3i (IC 50  = 1.20 μM, IC 50  = 1.10 μM), 3j (IC 50  = 0.11 μM, IC 50  = 0.18 μM), 3o (IC 50  = 0.98 μM, IC 50  = 2.76 μM) showed excellent inhibitory activity than the standard Etoposide (IC 50  = 2.11 μM, IC 50  = 3.08 μM) against MCF-7 and A-549 cell lines, respectively. Docking analysis of all the compounds with the human topoisomerase II revealed that the compound 3j fitted well in the active site pocket, showing the best docking score of 158.072 kcal/mol.
ISSN:0922-6168
1568-5675
DOI:10.1007/s11164-018-3434-9