ISSN:
1572-9001
Keywords:
X-ray structure
;
benzoxazine
;
synthesis
;
potassium channel modulators
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract With the aim of discovering new molecules with K+ channel modulating properties, we have synthesized analogues of cromakalim, an important molecule which shows specific affinity toward the K+ channels, by replacing the benzopyrane ring with a benzoxazine moiety. As a part of this study, we have synthesized and characterized, in solution and in the solid state as well, the compound ethyl [2,2-dimethyl-6-(Δ2-thiazolin-2-yl)-4H-l,4-benzoxazin-3-one-4-yl]butyrate (V). This compound exhibits in the solid state the following parameters: molecular formula C19H24N2O4S, triclinic, space group $$P\bar 1$$ , Mw = 376.5, a = 12.581(3) Å, b = 5.485(4) Å, c = 14.612(2) Å, α = 91.85(2), β = 108.9(3), γ = 82.04(4), V = 944.7 Å3, Z = 2, d = 1.323 g·cm−3. We describe here the synthesis and discuss the solid-state conformation of this new molecule; when tested on rat aorta ring precontracted with phenylephrine, the compound showed a concentration-dependent relaxation comparable to that measured for cromakalin taken as reference drug.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1022411920710
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