Bopindolol

Bopindolol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	C07AA17 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (RS)-1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate;
CAS Number	62658-63-3 ;
PubChem CID	44112;
DrugBank	DB08807 ;
ChemSpider	40146 ;
UNII	KT304VZO57;
KEGG	D07537 ;
ChEBI	CHEBI:76749;
ChEMBL	ChEMBL357995 ;
CompTox Dashboard (EPA)	DTXSID6022684 ;
Chemical and physical data
Formula	C23H28N2O3
Molar mass	380.488 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3;
	InChI InChI=1S/C23H28N2O3/c1-16-13-19-20(25-16)11-8-12-21(19)27-15-18(14-24-23(2,3)4)28-22(26)17-9-6-5-7-10-17/h5-13,18,24-25H,14-15H2,1-4H3 ; Key:UUOJIACWOAYWEZ-UHFFFAOYSA-N ;
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Bopindolol (INN) is a beta blocker. It is an ester which acts as a prodrug for its active metabolite 4-(3-t-butylamino-2-hydroxypropoxy)-2-methylindole.^[1]

Synthesis

The reaction of 4-Hydroxy-2-methylindole [35320-67-3] (1) with epichlorohydrin in the presence of lye led to 2-methyl-4-(oxiran-2-ylmethoxy)-1H-indole [62119-47-5] (2). Addition of tert-butylamine led to 4-(2-Hydroxy-3-tert-butylaminopropoxy)-2-methylindole [23869-98-9] (3). Ester formation with benzoic anhydride [93-97-0] (4) in the presence of hexamethylphosphoric acid triamide [680-31-9] completed the synthesis of Bopindolol (5).

References

^ Nagatomo T, Hosohata Y, Ohnuki T, Nakamura T, Hattori K, Suzuki J, Ishiguro M (Spring 2001). "Bopindolol: pharmacological basis and clinical implications". Cardiovascular Drug Reviews. 19 (1): 9–24. doi:10.1111/j.1527-3466.2001.tb00180.x. PMID 11314603.
^ DE2635209 idem Franz Troxler, Fritz Seemann, U.S. patent 4,434,176 (1984 to Sandoz Ltd.).
^ Franz Dr Troxler & Albert Dr Hofmann, CH453363 (1968 to Sandoz AG).