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Facile Synthesis of Novel 3‐(4‐phenylisothiazol‐5‐yl)‐2 H ‐chromen‐2‐one Derivatives as Potential Anticancer Agents
Author(s) -
Ambati Srinivasa Rao,
Gudala Satish,
Sharma Archi,
Penta Santhosh,
Reddy Velatooru Loka,
Bomma Yashwanth,
Janapala Venkateswara Rao,
Pola Someshwar
Publication year - 2017
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.2822
Subject(s) - chemistry , yield (engineering) , ammonium thiocyanate , regioselectivity , halogenation , ammonium acetate , pyrazole , combinatorial chemistry , isothiocyanate , stereochemistry , dimethylformamide , medicinal chemistry , catalysis , organic chemistry , materials science , high performance liquid chromatography , solvent , metallurgy
A series of 3‐(4‐phenylisothiazol‐5‐yl)‐2 H ‐chromen‐2‐one ( 6a – l ) derivatives has been efficiently synthesized by straightforward sequential reactions. Tandem Vilsmeier Hack reaction/cyclization/bromination/Suzuki cross‐coupling reactions were successfully applied to the preparation of title compounds in good‐to‐high yields. In the synthetic sequences, 3‐chloro‐3‐(2‐oxo‐2 H ‐chromen‐3‐yl)acrylaldehydes ( 2 ) were found to react with ammonium thiocyanate to yield the corresponding 3‐(isothiazol‐5‐yl)‐2 H ‐chromen‐2‐ones ( 3 ). These derivatives were brominated with N ‐bromo succinamide to yield the corresponding regioselective 3‐(4‐bromoisothiazol‐5‐yl)‐2 H ‐chromen‐2‐one ( 4 ). Finally, compound 4 was treated with various phenyl/pyrazole/7 H –pyrrolo[2,3‐d]pyrimidinyl boronic acids 5a – l in the presence of K 2 CO 3 and Pd catalyst in dimethylformamide to yield the corresponding title derivatives 6a – l . All the synthesized compounds were characterized by analytical and spectral studies. All the final compounds were screened against different cancer cell lines (A549, PC3, SKOV3, and B16F10), and among these compounds, 6b , 6g , 6h , and 6l displayed moderate cytotoxic activity against the tested cell lines.