Journal of Medicinal Chemistry p. 2403 - 2409 (1986)
Update date:2022-09-26
Topics:
Peet, Norton P.
Baugh, Larry E.
Sunder, Shyam
Lewis, Jon E.
Matthews, Emily H.
et al.
Syntheses for 3-(1H-tetrazol-5-yl)-4(3H)-quinazolinone sodium salt monohydrate (9; MDL 427) and the related formamido compound, 2-(formylamino)-N-1H-tetrazol-5-ylbenzamide (10), are described.Both compounds are active in the rat passive cutaneous anaphylaxis and passive peritoneal anaphylaxis tests.A 94:6 equilibrium mixture of 9 and ionized 10, respectively, forms in aqueous buffer systems at a pH-dependent rate.In addition, analogues of 3-(1H-tetrazol-5-yl)-4(3H)-quinazolinone (8) bearing substituents on the benzene ring, substituents at the 2-position, and heteroaryl groups at the 3-position other than tetrazole were prepared.These analogue sets demonstrated that an accessible electrophilic center and an acidic functionality were requirements for good antiallergic activity.
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