Chemistry:Ofornine
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]
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
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
- ↑ "Antihypertensive, vasodilating, and sympatholytic activities of ofornine® in spontaneously hypertensive rats". Drug Development Research 20 (3): 277–290. January 1990. doi:10.1002/ddr.430200303.
- ↑ "Synthesis of Ofornine mimics from natural product l-vasicine as anti-hypertensive agents". Bioorganic & Medicinal Chemistry 25 (4): 1440–1447. February 2017. doi:10.1016/j.bmc.2017.01.006. PMID 28110819.
- ↑ "Pyridine derivatives in the drug arsenal (150 years of pyridine chemistry)". Chemistry of Heterocyclic Compounds 31 (6): 639–650. June 1995. doi:10.1007/BF01169065.
- ↑ The organic chemistry of drug synthesis.. 4. Wiley. 1990. ISBN 978-0-471-85548-4.
- ↑ "Introduction to Retrosynthesis: Strategies and Approaches". E3S Web of Conferences 385: 04008. 2023. doi:10.1051/e3sconf/202338504008. ISSN 2267-1242. Bibcode: 2023E3SWC.38504008W.
- ↑ Bailey DM, "Antihypertensive pyridylaminobenzamide compounds", US patent 4610991, issued 9 September 1986, assigned to Sterling Drug Inc.
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