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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...
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Published in: | Research on chemical intermediates 2018-09, Vol.44 (9), p.5467-5481 |
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Main Authors: | , , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 0922-6168 1568-5675 |
DOI: | 10.1007/s11164-018-3434-9 |