tilisolol
{{short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 448141571
| IUPAC_name = (RS)-4-[3-(tert-butylamino)-2-hydroxypropoxy]-2-methylisoquinolin-1-one
| image = Tilisolol.svg
| chirality = Racemic mixture
| drug_name =
| tradename =
| Drugs.com = {{drugs.com|international|tilisolol}}
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status = Rx-only
| routes_of_administration = Oral
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 85136-71-6
| CAS_supplemental =
{{CAS|62774-96-3}} (hydrochloride)
| ATC_prefix = none
| ATC_suffix =
| ATC_supplemental =
| PubChem = 5474
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QUF41MF56G
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08598
| ChemSpiderID = 5275
| C=17 | H=24 | N=2 | O=3
| smiles = CC(C)(C)NCC(COC1=CN(C(=O)C2=CC=CC=C21)C)O
| StdInChI = 1S/C17H24N2O3/c1-17(2,3)18-9-12(20)11-22-15-10-19(4)16(21)14-8-6-5-7-13(14)15/h5-8,10,12,18,20H,9,11H2,1-4H3
| StdInChIKey = TWVUMMQUXMYOOH-UHFFFAOYSA-N
}}
Tilisolol (INN, trade name Selecal) is a beta blocker.{{cite journal | vauthors = Imaizumi T, Takeshita A, Nakamura N, Hirooka Y, Suzuki S, Yoshida M, Nakamura M | title = Vasodilating effect of the new beta-blocker tilisolol hydrochloride in humans | journal = Arzneimittel-Forschung | volume = 38 | issue = 9 | pages = 1342–4 | date = September 1988 | pmid = 2906248 | doi = | url = }}
Synthesis
The methanolysis of Phthalic anhydride [85-44-9] (1) gives Methyl hydrogen phthalate [4376-18-5] (2). Schotten-Baumann amidation with Methyl sarcosinate [5473-12-1] (3) gives Methyl 2-[(2-methoxy-2-oxoethyl)-methylcarbamoyl]benzoate, PC11644670 (4). Intramolecular lactamization with sodium methoxide afforded Methyl 4-hydroxy-2-methyl-1-oxoisoquinoline-3-carboxylate, PC54684295 (5). In lye saponification followed by decarboxylation occurred to give 4-hydroxy-2-methylisoquinolin-1(2H)-one [30236-50-1] (6). Treatment with Epichlorhydrin [106-89-8] (7) in the presence of base led to 2-Methyl-4-[(oxiran-2-yl)methoxy]isoquinolin-1(2H)-one [62775-08-0] (8). Opening of the oxirane ring with tert-Butylamine [75-64-9] (9) completed the synthesis of Tilisolol (10).
References
{{Reflist}}
{{Beta blockers}}
{{antihypertensive-stub}}