Utility of anhydrides for synthesis of new heterocyclic compounds with biological evaluation

Abstract

In the present study, a novel 8,9,10,11-tetrahydro-7H,14H-benzo[4',5']thieno[2',3':4,5]-1,3-oxazino[3,2-b]isoquinoline-7,14-dione 5 was prepare by condensation of 2-amino-3-carbethoxy-4,5,6,7-tetrahydro benzothiophene with homophthalic anhydride under microwave irradiation followed by alkaline hydrolysis and cyclization using acetyl chloride. Compound 5 was further allowed to react with different nitrogen nucleophiles to get new tetrahydrobenzothieno pyrimido isoquinolinone derivatives. The structures of the prepared compounds were elucidated by IR, 1H-NMR, 13C-NMR, and mass spectroscopy. The newly prepared compounds were tested in vitro against a panel of two human tumor cell lines, namely, hepatocellular carcinoma (liver) HepG2, and mammary gland breast MCF-7. Almost all the tested compounds showed satisfactory activity.