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Design, synthesis and Structure-Activity Relationship of novel Phenolic based Pyrimidine hybrids from Cashew Nut Shell Liquid (CNSL) components as potential antitumor agents

Dênis Pires de Lima, Thatikonda Narendar Reddy, Adilson Beatriz, Rosangela da Silva Lopes, Maria Rita Marques, Edson dos Anjos dos Santos, Camila Izabela Nantes, Maria de Fátima Cepa Matos, Renata Trentin Perdomo, Indiara Correia Pereira, Simone Schneider Weber

Abstract


Herein we describe a simple method for the synthesis of Baylis-Hillman adducts and their acetates by utilizing inexpensively available cashew nut shell liquid (CNSL) natural resources. Furthermore, by using a molecular hybridization approach, a series of novel pyrimidine scaffolds (15a-15t) were synthesized via utilizing Baylis-Hillman acetates derived from cashew nut shell liquid (CNSL). All the newly synthesized compounds were screened for their in vitro antitumor activity. Baylis-Hillman compounds 5b and 5h showed promising anticancer activity against MCF-7. Among pyrimidine derivatives, compounds 15i, 15j and 15l showed promising activity against HEP-G2, whereas compounds 15j, 15k, 15l and 15m showed promising activity against MCF-7. In addition, compound 15m showed significant activity against K562 when compared with the standard. The structure-activity relationship (SAR) analysis suggests that the length of the carbon chain of phenyl ring played an important role in the potency of activity.


Keywords


Cashew nut shell liquid; Baylis-Hillman adducts; pyrimidine derivatives; Anti-cancer activity

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ISSN 2347–9825