Jump to content

WB-4101: Difference between revisions

Edit links
From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
No edit summary
Tags: Mobile edit Mobile web edit
m Replace magic links with templates per local RfC and MediaWiki RfC
Line 19: Line 19:
}}
}}


'''WB-4101''' is a compound which acts as an [[Receptor antagonist|antagonist]] at the [[Alpha-1B adrenergic receptor|α<sub>1B</sub>-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.<ref>Green PN, Shapero M, Wilson C. The synthesis and pharmacological properties of a series of 2-substituted aminomethyl-1,4-benzodioxanes. ''Journal of Medicinal Chemistry''. 1969 Mar;12(2):326-9. PMID 5791620</ref><ref>Morrow AL, Creese I. Characterization of alpha 1-adrenergic receptor subtypes in rat brain: a reevaluation of [3H]WB4104 and [3H]prazosin binding. ''Molecular Pharmacology''. 1986 Apr;29(4):321-30. PMID 3010073</ref><ref>Melchiorre C, Bolognesi ML, Budriesi R, Chiarini A, Giardinà D, Minarini A, Quaglia W, Leonardi A. Search for selective antagonists at alpha 1-adrenoreceptors: neutral or negative antagonism? ''Farmaco''. 1998 Apr;53(4):278-86. PMID 9658586</ref><ref>Melchiorre C, Angeli P, Bolognesi ML, Chiarini A, Giardinà D, Gulini U, Leonardi A, Marucci G, Minarini A, Pigini M, Quaglia W, Rosini M, Tumiatti V. Alpha 1-adrenoreceptor antagonists bearing a quinazoline or a benzodioxane moiety. ''Pharmaceutica Acta Helvetiae''. 2000 Mar;74(2-3):181-90. PMID 10812956</ref><ref>Fumagalli L, Pallavicini M, Budriesi R, Gobbi M, Straniero V, Zagami M, Chiodini G, Bolchi C, Chiarini A, Micucci M, Valoti E. 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''. 2012 Dec;58:184-91. DOI 10.1016/j.ejmech.2012.09.049 PMID 23124215</ref><ref>Fumagalli L, Pallavicini M, Budriesi R, Bolchi C, Canovi M, Chiarini A, Chiodini G, Gobbi M, Laurino P, Micucci M, Straniero V, Valoti E. 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''. 2013 Aug 22;56(16):6402-12. DOI 10.1021/jm400867d PMID 23902232</ref>
'''WB-4101''' is a compound which acts as an [[Receptor antagonist|antagonist]] at the [[Alpha-1B adrenergic receptor|α<sub>1B</sub>-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.<ref>Green PN, Shapero M, Wilson C. The synthesis and pharmacological properties of a series of 2-substituted aminomethyl-1,4-benzodioxanes. ''Journal of Medicinal Chemistry''. 1969 Mar;12(2):326-9. {{PMID|5791620}}</ref><ref>Morrow AL, Creese I. Characterization of alpha 1-adrenergic receptor subtypes in rat brain: a reevaluation of [3H]WB4104 and [3H]prazosin binding. ''Molecular Pharmacology''. 1986 Apr;29(4):321-30. {{PMID|3010073}}</ref><ref>Melchiorre C, Bolognesi ML, Budriesi R, Chiarini A, Giardinà D, Minarini A, Quaglia W, Leonardi A. Search for selective antagonists at alpha 1-adrenoreceptors: neutral or negative antagonism? ''Farmaco''. 1998 Apr;53(4):278-86. {{PMID|9658586}}</ref><ref>Melchiorre C, Angeli P, Bolognesi ML, Chiarini A, Giardinà D, Gulini U, Leonardi A, Marucci G, Minarini A, Pigini M, Quaglia W, Rosini M, Tumiatti V. Alpha 1-adrenoreceptor antagonists bearing a quinazoline or a benzodioxane moiety. ''Pharmaceutica Acta Helvetiae''. 2000 Mar;74(2-3):181-90. {{PMID|10812956}}</ref><ref>Fumagalli L, Pallavicini M, Budriesi R, Gobbi M, Straniero V, Zagami M, Chiodini G, Bolchi C, Chiarini A, Micucci M, Valoti E. 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''. 2012 Dec;58:184-91. DOI 10.1016/j.ejmech.2012.09.049 {{PMID|23124215}}</ref><ref>Fumagalli L, Pallavicini M, Budriesi R, Bolchi C, Canovi M, Chiarini A, Chiodini G, Gobbi M, Laurino P, Micucci M, Straniero V, Valoti E. 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''. 2013 Aug 22;56(16):6402-12. DOI 10.1021/jm400867d {{PMID|23902232}}</ref>


==See also==
==See also==

Revision as of 22:43, 22 May 2017

WB-4101
Identifiers
  • 2-(2,6-Dimethoxyphenoxyethyl)aminomethyl-1,4-benzodioxane
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H23NO5
Molar mass345.389 g·mol−1
3D model (JSmol)
  • COc1cccc(c1OCCNCC2COc3ccccc3O2)OC
  • 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 α1B-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]

See also


References

  1. ^ Green PN, Shapero M, Wilson C. The synthesis and pharmacological properties of a series of 2-substituted aminomethyl-1,4-benzodioxanes. Journal of Medicinal Chemistry. 1969 Mar;12(2):326-9. PMID 5791620
  2. ^ Morrow AL, Creese I. Characterization of alpha 1-adrenergic receptor subtypes in rat brain: a reevaluation of [3H]WB4104 and [3H]prazosin binding. Molecular Pharmacology. 1986 Apr;29(4):321-30. PMID 3010073
  3. ^ Melchiorre C, Bolognesi ML, Budriesi R, Chiarini A, Giardinà D, Minarini A, Quaglia W, Leonardi A. Search for selective antagonists at alpha 1-adrenoreceptors: neutral or negative antagonism? Farmaco. 1998 Apr;53(4):278-86. PMID 9658586
  4. ^ Melchiorre C, Angeli P, Bolognesi ML, Chiarini A, Giardinà D, Gulini U, Leonardi A, Marucci G, Minarini A, Pigini M, Quaglia W, Rosini M, Tumiatti V. Alpha 1-adrenoreceptor antagonists bearing a quinazoline or a benzodioxane moiety. Pharmaceutica Acta Helvetiae. 2000 Mar;74(2-3):181-90. PMID 10812956
  5. ^ Fumagalli L, Pallavicini M, Budriesi R, Gobbi M, Straniero V, Zagami M, Chiodini G, Bolchi C, Chiarini A, Micucci M, Valoti E. 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. 2012 Dec;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, Chiodini G, Gobbi M, Laurino P, Micucci M, Straniero V, Valoti E. 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. 2013 Aug 22;56(16):6402-12. DOI 10.1021/jm400867d PMID 23902232



Stub icon

This pharmacology-related article is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=WB-4101&oldid=781734359"