Ultrasound Assisted Synthesis of 3-(het)aryl Isocoumarin Derivatives and their in vitro Pharmacological Evaluation

Author(s): Gutta Lakshmi Prasanna, V. D. Nagendra Kumar Abbaraju, Yarlagadda Bharath, Mandava V. Basaveswara Rao, Manojit Pal*.

Journal Name: Mini-Reviews in Medicinal Chemistry

Volume 19 , Issue 10 , 2019

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Background: In view of numerous biological activities of 3-substituted isocoumarins a number of analogues based on this scaffold were synthesized for their in vitro pharmacological evaluation.

Methods: The syntheses of 3-substituted isocoumarins were carried out via a Pd/C-catalyzed Suzuki- Miyaura coupling of 3-chloroisochromen-1-one with a range of boronic acid derivatives. This C-C bond forming reaction was facilitated by ultrasound irradiation to afford the desired products in good yields. A number of 3-(het)aryl isocoumarin derivatives were prepared by using this methodology and subsequently tested for their TNF-α inhibitory properties in vitro followed by cytotoxicities via the MTT assay.

Results: Several compounds showed inhibition of TNF-α with one compound showing an IC50 value of 9.01±1.25 μM. Three compounds also showed promising cytotoxic properties against two cancer cell lines with IC50 ~ 0.9-2.7 μM.

Conclusion: The isocoumarin framework could be an effective template for the design and discovery of new inhibitor of TNF-α for the potential treatment of related diseases.

Keywords: Isocoumarin, Suzuki-Miyaura coupling, Pd/C, TNF-α, inhibition, pharmacological evaluation.

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Article Details

Year: 2019
Page: [842 - 850]
Pages: 9
DOI: 10.2174/1389557519666190130163708
Price: $95

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