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

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

Volume: 18 Issue: 17

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

Affiliation:

• Department of Chemistry, Krishna University, Machilipatnam-521001, Andhra Pradesh,India

• Dr. Reddy`s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046,India

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

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.

Cite this article as:

Suman Kancharla, Bharath Yarlagadda , Anuradha V. , Rao V. Basaveswara Mandava *, Pal Manojit*, Ultrasound Assisted One-pot and Sequential Synthesis of 3-methyleneisoindolin-1-ones and their in vitro Evaluation, Mini-Reviews in Medicinal Chemistry 2018; 18 (17) . https://dx.doi.org/10.2174/1389557517666170728164620