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A series of 2,2,8,8-tetramethyl-2,3,7,8-tetrahydro-4,6-diamino-3,7-dihydroxy-6,7-epoxy-benzo-[1,2-b:5,4-b']dipyran derivatives 7a-e and 8a-e were synthesized from resorcinol. All the synthesized compounds were characterized by FTIR, mass spectra, and 1H NMR. These compounds were evaluated for antihypertensive activity using Wister Albino Rat model. Direct antihypertensive activity was performed using the instrument BIOPAC System MP-36 Santa Barbara, California, for recording blood pressure response. Among the title compounds, compounds 7b, 7c, and 7d showed potent antihypertensive activity and other compounds were also found to exert low and moderate antihypertensive activity. The relaxant potency in rat aorta and trachea was used for biological characterization of the benzopyrans. Structure-activity relationships study was investigated around position-4 of the benzopyran nucleus.
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