From Wikipedia, the free encyclopedia
Flestolol
Names
IUPAC name
3-{[1-(Carbamoylamino)-2-methyl-2-propanyl]amino}-2-hydroxypropyl 2-fluorobenzoate
Identifiers
ChemSpider
KEGG
UNII
InChI=1S/C15H22FN3O4/c1-15(2,9-18-14(17)22)19-7-10(20)8-23-13(21)11-5-3-4-6-12(11)16/h3-6,10,19-20H,7-9H2,1-2H3,(H3,17,18,22)
Key: ZPLOQFLCMVIWRY-UHFFFAOYSA-N
CC(C)(CNC(=O)N)NCC(COC(=O)C1=CC=CC=C1F)O
Properties
C 15 H 22 F N 3 O 4
Molar mass
327.356 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Flestolol is a short-acting
beta adrenergic receptor antagonist .
[1]
Synthesis
Flestolol synthesis:
[2]
Acylation of
glycidol (2 ) with the
acid chloride 1 produces the ester 3 . Reaction of that intermediate with amine 4 , obtained by reaction of 1,1-dimethylethylenediamine with urea, gives flestolol (5 ).
References
^ Quon, CY; Stampfli, HF (1993). "Biochemical characterization of flestolol esterase". Research communications in chemical pathology and pharmacology . 81 (3): 309–22.
PMID
8235065 .
^ Kam, Sheung Tsam; Matier, William L.; Mai, Khuong X.; Barcelon-Yang, Cynthia; Borgman, Robert J.; O'Donnell, John P.; Stampfli, Herman F.; Sum, Check Y.; Anderson, William G. (1984). "[(Arylcarbonyl)oxy]propanolamines. 1. Novel .beta.-blockers with ultrashort duration of action". Journal of Medicinal Chemistry . 27 (8): 1007.
doi :
10.1021/jm00374a013 .
PMID
6146718 .
α1
Agonists Antagonists
Abanoquil
Ajmalicine
Alfuzosin
Anisodamine
Anisodine
Atiprosin
Atypical antipsychotics (e.g.,
brexpiprazole ,
clozapine ,
olanzapine ,
quetiapine ,
risperidone )
Benoxathian
Beta blockers (e.g.,
adimolol ,
amosulalol ,
arotinolol ,
carvedilol ,
eugenodilol ,
labetalol )
Buflomedil
Bunazosin
Corynanthine
Dapiprazole
Domesticine
Doxazosin
Ergolines (e.g.,
acetergamine ,
ergotamine ,
dihydroergotamine ,
lisuride ,
nicergoline ,
terguride )
Etoperidone
Fenspiride
Hydroxyzine
Indoramin
Ketanserin
L-765,314
mCPP
Mepiprazole
Metazosin
Monatepil
Moxisylyte
Naftopidil
Nantenine
Neldazosin
Niaprazine
Niguldipine
Pardoprunox
Pelanserin
Perlapine
Phendioxan
Phenoxybenzamine
Phentolamine
Phenylpiperazine
antidepressants (e.g.,
hydroxynefazodone ,
nefazodone ,
trazodone ,
triazoledione )
Piperoxan
Prazosin
Quinazosin
Quinidine
Silodosin
Spegatrine
Spiperone
Talipexole
Tamsulosin
Terazosin
Tiodazosin
Tolazoline
Tetracyclic antidepressants (e.g.,
amoxapine ,
maprotiline ,
mianserin )
Tricyclic antidepressants (e.g.,
amitriptyline ,
clomipramine ,
doxepin ,
imipramine ,
trimipramine )
Trimazosin
Typical antipsychotics (e.g.,
chlorpromazine ,
fluphenazine ,
loxapine ,
thioridazine )
Urapidil
WB-4101
Zolertine
α2
Agonists Antagonists
1-PP
Adimolol
Amesergide
Aptazapine
Atipamezole
Atypical antipsychotics (e.g.,
asenapine ,
brexpiprazole ,
clozapine ,
lurasidone ,
olanzapine ,
paliperidone ,
quetiapine ,
risperidone ,
zotepine )
Azapirones (e.g.,
buspirone ,
gepirone ,
ipsapirone ,
tandospirone )
BRL-44408
Buflomedil
Cirazoline
Efaroxan
Esmirtazapine
Fenmetozole
Fluparoxan
Idazoxan
Ketanserin
Lisuride
mCPP
Mianserin
Mirtazapine
NAN-190
Pardoprunox
Phentolamine
Phenoxybenzamine
Piperoxan
Piribedil
Rauwolscine
Rotigotine
Setiptiline
Spegatrine
Spiroxatrine
Sunepitron
Terguride
Tolazoline
Typical antipsychotics (e.g.,
chlorpromazine ,
fluphenazine ,
loxapine ,
thioridazine )
Yohimbine
β