Síntese e avaliação da atividade biológica de um novo análogo aromático do estrigol

Abstract

This work reports the synthesis of a new strigol aromatic analogue 48. The analogue was synthetized from natural safrole 44 and preliminary evaluation of its biological activity concerning to stimulation of lettuce seeds growing and its toxicity obtained in Artemia salina, Leach test was described. Reaction of isomerization of safrole 44 and further ciclization using Vielsmeyer-Haack reactant produced the key intermediate indanone 52. Subsequent base-catalysed reaction and production of an enolate led to keto-ester 51. This species produced lactone 50 by a selective reduction and further ciclization. Formylation of this intermediate produced the enol-ether 49. Molecular modelling and analysis of the spectrometric data made possible to observe keto-enolic tautomerism and the Z sterochemistry of this product. A coupling by Oalkylation of the enol-ether using bromobutenolide 32 yielded a mixture of epimers of the new aromatic analogue 48 with an overall yield of 20%. Diastereomers were separated by semipreparative HPLC in normal phase. Preliminary tests to evaluate biological activity showed good results concerning the growth of lettuce seeds (Lactuca sativa L.) and the test with Artemia salina, Leach demostrated its Iow toxicity