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Palladium Catalyzed Tricyclohexylphosphine Ligand Associated Synthesis of N ‐(2‐(pyridine‐4‐yl)‐1 H ‐pyrrolo[3,2‐ c ]‐pyridin‐6‐yl‐(substituted)‐sulfonamide Derivatives as Antiproliferative Agents
Author(s) -
Pawar Chandrakant D.,
Sarkate Aniket P.,
Karnik Kshipra S.,
Shinde Devanand B.
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3206
Subject(s) - chemistry , sulfonamide , pyridine , hela , tricyclohexylphosphine , stereochemistry , palladium , cell culture , ligand (biochemistry) , catalysis , medicinal chemistry , in vitro , receptor , organic chemistry , biochemistry , phosphine , biology , genetics
A series of novel N ‐(2‐(pyridine‐4‐yl)‐1 H ‐pyrrolo[3,2‐ c ]‐pyridin‐6‐yl‐(substituted)‐sulfonamide derivatives were synthesized from 2‐bromo‐6‐nitro‐1 H ‐pyrrolo[3,2‐ c ]pyridine through a series of reactions including Suzuki reaction, reduction, protection, and sulfonamide coupling. All the synthesized compounds were screened for anticancer activity against MCF‐7, HeLa, A‐549, and Du‐145 cancer cell lines by the MTT assay. The preliminary bioassay suggests that most of the compounds show antiproliferation with different degrees. Doxorubicin was used as a positive control. Among the synthesized compounds, 8d and 8h were most active compared with the standard in cell line data. The synthesized compounds 8d and 8h show IC 50 values in the range of 1.88–5.16 μM for all the cell lines. Compounds 8d and 8h were further studied for a panel of eight human kinase at 10 μM concentrations and the result shows 64% to 70% inhibitions for both Aurora‐A and Aurora‐B kinase.