Ofornine

Ofornine
Clinical data
Other names	Win 48049
Identifiers
	IUPAC name 1-Piperidinyl(2-(4-pyridinylamino)phenyl)methanone;
CAS Number	87784-12-1;
PubChem CID	55754;
ChemSpider	50349;
UNII	WK1LBP1F3L;
KEGG	D05234;
ChEMBL	ChEMBL2105194;
CompTox Dashboard (EPA)	DTXSID60236626 ;
ECHA InfoCard	100.081.195
Chemical and physical data
Formula	C17H19N3O
Molar mass	281.359 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CCN(CC1)C(=O)C2=CC=CC=C2NC3=CC=NC=C3;
	InChI 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;

Antihypertensive drug

Pharmaceutical compound

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

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

^ Defelice A, Lape H, Horan P, Frering R, Brousseau A, O'Connor B, et al. (January 1990). "Antihypertensive, vasodilating, and sympatholytic activities of ofornine® in spontaneously hypertensive rats". Drug Development Research. 20 (3): 277–290. doi:10.1002/ddr.430200303.
^ Mushtaq A, Rayees S, Rouf A, Kumar B, Sharma A, Nagaraju PV, et al. (February 2017). "Synthesis of Ofornine mimics from natural product l-vasicine as anti-hypertensive agents". Bioorganic & Medicinal Chemistry. 25 (4): 1440–1447. doi:10.1016/j.bmc.2017.01.006. PMID 28110819.
^ Lukevits E (June 1995). "Pyridine derivatives in the drug arsenal (150 years of pyridine chemistry)". Chemistry of Heterocyclic Compounds. 31 (6): 639–650. doi:10.1007/BF01169065.
^ Lednicer D, Mitscher LA (1990). The organic chemistry of drug synthesis. Vol. 4. Wiley. ISBN 978-0-471-85548-4.
^ Wang H, Wei G (2023). Ganesapillai M, Abdullah AZ (eds.). "Introduction to Retrosynthesis: Strategies and Approaches". E3S Web of Conferences. 385: 04008. Bibcode:2023E3SWC.38504008W. doi:10.1051/e3sconf/202338504008. ISSN 2267-1242.
^ US 4610991, Bailey DM, "Antihypertensive pyridylaminobenzamide compounds", issued 9 September 1986, assigned to Sterling Drug Inc.

[1] Defelice A, Lape H, Horan P, Frering R, Brousseau A, O'Connor B, et al. (January 1990). "Antihypertensive, vasodilating, and sympatholytic activities of ofornine® in spontaneously hypertensive rats". Drug Development Research. 20 (3): 277–290. doi:10.1002/ddr.430200303.

[2] Mushtaq A, Rayees S, Rouf A, Kumar B, Sharma A, Nagaraju PV, et al. (February 2017). "Synthesis of Ofornine mimics from natural product l-vasicine as anti-hypertensive agents". Bioorganic & Medicinal Chemistry. 25 (4): 1440–1447. doi:10.1016/j.bmc.2017.01.006. PMID 28110819.

[3] Lukevits E (June 1995). "Pyridine derivatives in the drug arsenal (150 years of pyridine chemistry)". Chemistry of Heterocyclic Compounds. 31 (6): 639–650. doi:10.1007/BF01169065.

[4] Lednicer D, Mitscher LA (1990). The organic chemistry of drug synthesis. Vol. 4. Wiley. ISBN 978-0-471-85548-4.

[5] Wang H, Wei G (2023). Ganesapillai M, Abdullah AZ (eds.). "Introduction to Retrosynthesis: Strategies and Approaches". E3S Web of Conferences. 385: 04008. Bibcode:2023E3SWC.38504008W. doi:10.1051/e3sconf/202338504008. ISSN 2267-1242.

[6] US 4610991, Bailey DM, "Antihypertensive pyridylaminobenzamide compounds", issued 9 September 1986, assigned to Sterling Drug Inc.