Adibendan
Chemical compound
From Wikipedia, the free encyclopedia
Adibendan is an inhibitor of phosphodiesterase 3. It has been tested in dogs for its effects on heart output and dilation of blood vessels.[1]
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| Names | |
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| Preferred IUPAC name
7,7-Dimethyl-2-(pyridin-4-yl)-5,7-dihydroimidazo[4,5-f]indol-6(1H)-one | |
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3D model (JSmol) |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C16H14N4O | |
| Molar mass | 278.315 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
Synthesis:[2] Patent (Ex 14):[3]
N-benzyloxindole [7135-32-2] (1) is the starting material. Base facilitated alkylation with 2 molar equivalents of methyl halide (via the enolate stabilized carbanion) gives 1-benzyl-3,3-dimethylindol-2-one, PC11086219. Dissolving metal reduction (sodamide generated in situ) was the reaction medium which was employed to cleave the benzyl protecting group to give 3,3-dimethyloxindole [19155-24-9] (2). Nitration of this can obviously be achieved by the nitronium ion (generated in situ from nitric and sulfuric acids) to give 3,3-dimethyl-5-nitro-oxindole [100511-00-0]. Catalytic hydrogenation over palladium then reduces the nitro group to give 3,3-dimethyl-5-amino-oxindole [31523-05-4] (3). Treatment with acetic anhydride protects amino groups as the acetamide. Treatment with nitric acid is then able to add a nitro group on to the aromatic ring which is probably sterically directed. Treatment with acid hydrolyses the acetamide protecting groups to give 3,3-dimethyl-5-amino-6-nitro-oxindole, PC22162178 (4). Catalytic hydrogenation over platinum oxide reduces the nitro group to give 3,3-dimethyl-5,6-diamino-oxindole [100568-79-4]. The last step of the reaction sequence is a condensation with Isonicotinaldehyde [872-85-5], thus completing the synthesis of adibendan (5), respectively.
