Zolertine

Last updated
Zolertine
Zolertine.svg
Names
IUPAC name
1-Phenyl-4-[2-(tetrazol-5-yl)ethyl]piperazine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C13H18N6/c1-2-4-12(5-3-1)19-10-8-18(9-11-19)7-6-13-14-16-17-15-13/h1-5H,6-11H2,(H,14,15,16,17)
    Key: XTTHMUYLNLEJRS-UHFFFAOYSA-N
  • InChI=1/C13H18N6/c1-2-4-12(5-3-1)19-10-8-18(9-11-19)7-6-13-14-16-17-15-13/h1-5H,6-11H2,(H,14,15,16,17)
    Key: XTTHMUYLNLEJRS-UHFFFAOYAE
  • C1CN(CCN1CCC2=NNN=N2)C3=CC=CC=C3
Properties
C13H18N6
Molar mass 258.329 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Zolertine is an alpha-1 adrenoceptor antagonist. [1]

Synthesis

Synthesis: Patent: Zolertine synthesis.svg
Synthesis: Patent:

The conjugate addition between phenylpiperazine [92-54-6] (1) and acrylonitrile (2) gives 3-(4-phenylpiperazin-1-yl)propanenitrile [18505-84-5] (3). The nitrile is converted to a tetrazole ring via a 1,3-dipolar addition process with sodium azide under ammonium chloride catalysis.

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References

  1. Ibarra, M; Hong, E; Villalobos-Molina, R (2000). "The alpha-adrenoceptor antagonist, zolertine, inhibits alpha1D- and alpha1A-adrenoceptor-mediated vasoconstriction in vitro". Journal of Autonomic Pharmacology. 20 (3): 139–45. doi:10.1046/j.1365-2680.2000.00172.x. PMID   11193002.
  2. Hayao, Shin.; Havera, Herbert J.; Strycker, Wallace G.; Leipzig, T. J.; Rodriguez, Rodolfo. (1967). "New Antihypertensive Aminoalkyltetrazoles". Journal of Medicinal Chemistry 10 (3): 400–402. doi:10.1021/jm00315a025.
  3. BE661396 idem Strycker Wallace Glenn, Hayao Shin, U.S. Patent 3,231,574 (1966 to Miles Lab).