WB-4101

WB-4101
Identifiers
	IUPAC name 2-(2,6-Dimethoxyphenoxyethyl)aminomethyl-1,4-benzodioxane;
CAS Number	613-67-2 ;
PubChem CID	5685;
IUPHAR/BPS	499;
ChemSpider	5483;
UNII	E9H51OIT2B;
CompTox Dashboard (EPA)	DTXSID1043885 ;
Chemical and physical data
Formula	C19H23NO5
Molar mass	345.395 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cccc(c1OCCNCC2COc3ccccc3O2)OC;
	InChI InChI=1S/C19H23NO5/c1-21-17-8-5-9-18(22-2)19(17)23-11-10-20-12-14-13-24-15-6-3-4-7-16(15)25-14/h3-9,14,20H,10-13H2,1-2H3; Key:GYSZUJHYXCZAKI-UHFFFAOYSA-N;

WB-4101 is a compound which acts as an antagonist at the α_1B-adrenergic receptor. It was one of the first selective antagonists developed for this receptor and was invented in 1969, but is still commonly used in research into adrenergic receptors, especially as a lead compound from which to develop more selective drugs.^[1]^[2]^[3]^[4]^[5]^[6]

References

^ Green PN, Shapero M, Wilson C (March 1969). "The synthesis and pharmacological properties of a series of 2-substituted aminomethyl-1,4-benzodioxanes". Journal of Medicinal Chemistry. 12 (2): 326–9. doi:10.1021/jm00302a033. PMID 5791620.
^ Morrow AL, Creese I (April 1986). "Characterization of alpha 1-adrenergic receptor subtypes in rat brain: a reevaluation of [3H]WB4104 and [3H]prazosin binding". Molecular Pharmacology. 29 (4): 321–30. PMID 3010073.
^ Melchiorre C, Bolognesi ML, Budriesi R, Chiarini A, Giardinà D, Minarini A, et al. (April 1998). "Search for selective antagonists at alpha 1-adrenoreceptors: neutral or negative antagonism?". Farmaco. 53 (4): 278–86. doi:10.1016/S0014-827X(98)00022-6. PMID 9658586.
^ Melchiorre C, Angeli P, Bolognesi ML, Chiarini A, Giardinà D, Gulini U, et al. (March 2000). "Alpha 1-adrenoreceptor antagonists bearing a quinazoline or a benzodioxane moiety". Pharmaceutica Acta Helvetiae. 74 (2–3): 181–90. doi:10.1016/S0031-6865(99)00049-7. PMID 10812956.
^ Fumagalli L, Pallavicini M, Budriesi R, Gobbi M, Straniero V, Zagami M, et al. (December 2012). "Affinity and activity profiling of unichiral 8-substituted 1,4-benzodioxane analogues of WB4101 reveals a potent and selective α1B-adrenoceptor antagonist". European Journal of Medicinal Chemistry. 58: 184–91. doi:10.1016/j.ejmech.2012.09.049. PMID 23124215.
^ Fumagalli L, Pallavicini M, Budriesi R, Bolchi C, Canovi M, Chiarini A, et al. (August 2013). "6-methoxy-7-benzofuranoxy and 6-methoxy-7-indolyloxy analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 discovery of a potent and selective α1D-adrenoceptor antagonist". Journal of Medicinal Chemistry. 56 (16): 6402–12. doi:10.1021/jm400867d. PMID 23902232.

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[1] Green PN, Shapero M, Wilson C (March 1969). "The synthesis and pharmacological properties of a series of 2-substituted aminomethyl-1,4-benzodioxanes". Journal of Medicinal Chemistry. 12 (2): 326–9. doi:10.1021/jm00302a033. PMID 5791620.

[2] Morrow AL, Creese I (April 1986). "Characterization of alpha 1-adrenergic receptor subtypes in rat brain: a reevaluation of [3H]WB4104 and [3H]prazosin binding". Molecular Pharmacology. 29 (4): 321–30. PMID 3010073.

[3] Melchiorre C, Bolognesi ML, Budriesi R, Chiarini A, Giardinà D, Minarini A, et al. (April 1998). "Search for selective antagonists at alpha 1-adrenoreceptors: neutral or negative antagonism?". Farmaco. 53 (4): 278–86. doi:10.1016/S0014-827X(98)00022-6. PMID 9658586.

[4] Melchiorre C, Angeli P, Bolognesi ML, Chiarini A, Giardinà D, Gulini U, et al. (March 2000). "Alpha 1-adrenoreceptor antagonists bearing a quinazoline or a benzodioxane moiety". Pharmaceutica Acta Helvetiae. 74 (2–3): 181–90. doi:10.1016/S0031-6865(99)00049-7. PMID 10812956.

[5] Fumagalli L, Pallavicini M, Budriesi R, Gobbi M, Straniero V, Zagami M, et al. (December 2012). "Affinity and activity profiling of unichiral 8-substituted 1,4-benzodioxane analogues of WB4101 reveals a potent and selective α1B-adrenoceptor antagonist". European Journal of Medicinal Chemistry. 58: 184–91. doi:10.1016/j.ejmech.2012.09.049. PMID 23124215.

[6] Fumagalli L, Pallavicini M, Budriesi R, Bolchi C, Canovi M, Chiarini A, et al. (August 2013). "6-methoxy-7-benzofuranoxy and 6-methoxy-7-indolyloxy analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 discovery of a potent and selective α1D-adrenoceptor antagonist". Journal of Medicinal Chemistry. 56 (16): 6402–12. doi:10.1021/jm400867d. PMID 23902232.

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See also

References