Befunolol

Befunolol (INN) is a beta blocker with intrinsic sympathomimetic activity used in the management of open-angle glaucoma.^[1] It also acts as a β adrenoreceptor partial agonist.^[2][3] Befunolol was introduced in Japan in 1983 by Kakenyaku Kako Co. under the trade name Bentos.^[4]

Befunolol

Clinical data
Trade names	Benfuran, Bentos, Betaclar, Glauconex
AHFS/Drugs.com	International Drug Names
ATC code	S01ED06 (WHO)
Identifiers
IUPAC name (RS)-1-{{#parsoidfragment:2}}{7-[2-hydroxy-3-(propan-2-ylamino)propoxy]- 1-benzofuran-2-yl}ethanone
CAS Number	39552-01-7 Y
PubChem CID	2309
DrugBank	DB09013 Y
ChemSpider	2219 Y
UNII	418546MT3A
KEGG	D07496 Y
ChEMBL	ChEMBL153984 Y
CompTox Dashboard (EPA)	DTXSID80865957
Chemical and physical data
Formula	C16H21NO4
Molar mass	291.347 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(c2oc1c(OCC(O)CNC(C)C)cccc1c2)C
InChI InChI=1S/C16H21NO4/c1-10(2)17-8-13(19)9-20-14-6-4-5-12-7-15(11(3)18)21-16(12)14/h4-7,10,13,17,19H,8-9H2,1-3H3 Y Key:ZPQPDBIHYCBNIG-UHFFFAOYSA-N Y

Synthesis

The first reported synthesis of befunolol in 1974 used a benzofuran derivative (4) with epichlorohydrin and then isopropylamine to add the sidechain which was known to produce beta blockers, by analogy with drugs discovered by Imperial Chemical Industries, such as propanolol.^[5] The requisite intermediate was synthesized from ortho-vanillin (1) by a condensation reaction with chloroacetone (2) in the presence of potassium hydroxide, giving 2-acetyl-7-methoxybenzofuran (3), which was demethylated using hydrobromic acid.^[6][7][8]