We report herein the design and synthesis of 17 new spiroheterocycles 10-26, on the basis of two hypothetical pharmacophore structures designed to interact with both of Mycobacterium tuberculosis bacteria and HIV-1 virus. The in vitro biological evaluation of these compounds allowed us to point out seven new potential non-nucleoside hits, with MIC values in the range of 6.25 µg/mL and two new potential anti-HIV-1 inhibitors .

The title compound, C(19)H(15)NO(6), contains a planar isoxazole ring. An intramolecular hydrogen bond is formed between the OH group attached to a phenyl ring and a carbonyl O atom.

Synthesis of New Spiro-[isothiochromene-3,5'-isoxazolidin]-4(1H)-ones. -Title compounds (III) are formed regiospecifically via 1,3-dipolar cycloaddition reaction. -(BENNANI, B.; JALBOUT, A. F.; BABA, B. F.; BEN LARBI, N.; BOUKIR, A.; KERBAL*, A.; MIMOUNI, M.; BEN HADDA, T.; TRZASKOWSKI, B.; J. Heterocycl. Chem. 44 (2007) 3, 711-716; Lab. Chim. Org., Fac. Sci., Univ. Sidi Mohamed Ben Abdellah, Dhar El Mahraz, 30000 Fes, Morocco; Eng.) -H. Haber 38-136

A series of seven new 2′,3′,4′‐substituted spiro[isothiochromene‐3,5′‐isoxazolidin]‐4(1H)‐ones (7‐13) has been prepared in the reaction of benzylidene(phenyl)azane oxide (5) or benzylidene(methyl)azane oxide (6) with (3Z)‐3‐(4‐substituted‐benzylidene)‐1H‐isothio‐ chromen‐4(3H)‐one (1‐4). The reaction occurs by a 1,3‐dipolar cycloaddition mechanism that leads to the regiospecific formation of various spiroisoxazolidines (7‐13).

No abstract