Ofornine

Antihypertensive drug From Wikipedia, the free encyclopedia

Ofornine is a synthetic compound investigated primarily for its antihypertensive properties. It functions as a vasodilator and exhibits presynaptic adrenolytic activity, with evidence suggesting involvement of dopaminergic mechanisms in its pharmacological effects.[1]

Other namesWin 48049
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Ofornine
Clinical data
Other namesWin 48049
Identifiers
  • 1-Piperidinyl(2-(4-pyridinylamino)phenyl)methanone
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ECHA InfoCard100.081.195 Edit this at Wikidata
Chemical and physical data
FormulaC17H19N3O
Molar mass281.359 g·mol−1
3D model (JSmol)
  • C1CCN(CC1)C(=O)C2=CC=CC=C2NC3=CC=NC=C3
  • InChI=1S/C17H19N3O/c21-17(20-12-4-1-5-13-20)15-6-2-3-7-16(15)19-14-8-10-18-11-9-14/h2-3,6-11H,1,4-5,12-13H2,(H,18,19)
  • Key:YMODINPJYNHPTM-UHFFFAOYSA-N
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A number of structural analogs have been prepared with similar activity.[2]

Chemistry

Ofornine contains a pyridine moiety,[3] or more specifically a fampridine or anthranilamide (c.f. fenamate).

Synthesis

Synthesis:[4][5] Patent:[6]

Reaction between 4-chloropyridine [626-61-9] HCl: [7379-35-3] (1) and anthranilic acid [118-92-3] (2) gives 2-(4-pyridylamino)benzoic acid [34861-30-8] (3). Halogenation with thionyl chloride gave 2-(4-pyridinylamino)-benzoyl chloride [89989-83-3] (4). Amide formation with piperidine [110-89-4] (5) completed the synthesis of Ofornine (6).

References

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