Ultrasound Assisted One-pot and Sequential Synthesis of 3-methyleneisoindolin-1-ones and their in vitro Evaluation

Author(s): Kancharla Suman, Yarlagadda Bharath, V. Anuradha, Mandava V. Basaveswara Rao*, Manojit Pal*.

Journal Name: Mini-Reviews in Medicinal Chemistry

Volume 18 , Issue 17 , 2018

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Graphical Abstract:


Background: 3-Methyleneisoindolin-1-one derivatives containing a pyridin-2-ylmethyl substituent on their ring nitrogen were designed as potential bioactive agents. A one-pot synthesis of these compounds was achieved via sequential C-C coupling, followed by C-Si bond cleavage and subsequent tandem C-C/C-N bond forming reaction under ultrasound irradiation.

Method: The methodology involved coupling of (trimethylsilyl)acetylene with iodoarenes in the presence of 10% Pd/C-CuI-PPh3-Et3N in MeOH followed by treating the reaction mixture with K2CO3 in aqueous MeOH, and finally coupling with 2-iodo-N-(pyridin-2-ylmethyl)benzamide. The in vitro evaluation of these compounds was performed to identify some initial hit molecules one of which showed dose dependent inhibition of PDE4B.

Keywords: 3-Methyleneisoindolin-1-one, ultrasound, Pd/C, PDE4, C-Si bond, MeOH.

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Article Details

Year: 2018
Page: [1498 - 1505]
Pages: 8
DOI: 10.2174/1389557517666170728164620
Price: $58

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