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Pelanserin

From Wikipedia, the free encyclopedia
Pelanserin
Names
Preferred IUPAC name
3-[3-(4-Phenylpiperazin-1-yl)propyl]quinazoline-2,4(1H,3H)-dione
Other names
TR2515
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C21H24N4O2/c26-20-18-9-4-5-10-19(18)22-21(27)25(20)12-6-11-23-13-15-24(16-14-23)17-7-2-1-3-8-17/h1-5,7-10H,6,11-16H2,(H,22,27)
    Key: WPKPLSFHHBBLRY-UHFFFAOYSA-N
  • InChI=1/C21H24N4O2/c26-20-18-9-4-5-10-19(18)22-21(27)25(20)12-6-11-23-13-15-24(16-14-23)17-7-2-1-3-8-17/h1-5,7-10H,6,11-16H2,(H,22,27)
    Key: WPKPLSFHHBBLRY-UHFFFAOYAV
  • C1CN(CCN1CCCN2C(=O)C3=CC=CC=C3NC2=O)C4=CC=CC=C4
Properties
C21H24N4O2
Molar mass364.449 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Pelanserin (TR2515) is a chemical compound that acts as anantagonist of the5-HT2 andα1-adrenergic receptors.[1]

Synthesis

[edit]
Synthesis of pelanserin

Pelanserin (3) can besynthesized by a reaction betweenisatoic anhydride (1) and 1-(3-aminopropyl)-4-phenylpiperazine (2) in the presence ofphosgene.[2][3][4][5][6][7][8][9]

See also

[edit]

References

[edit]
  1. ^Villalobos-Molina, R; Ibarra, M; Hong, E (1995). "The 5-HT2 receptor antagonist, pelanserin, inhibits alpha 1-adrenoceptor-mediated vasoconstriction in vitro".European Journal of Pharmacology.277 (2–3):181–5.doi:10.1016/0014-2999(95)00074-u.PMID 7493607.
  2. ^Hayao, Shin; Havera, Herbert J.; Strycker, Wallace G.; Leipzig, T. J.; Kulp, Richard A.; Hartzler, Harold E. (1965). "New Sedative and Hypotensive 3-Substituted 2,4(1H,3H)-Quinazolinediones".Journal of Medicinal Chemistry.8 (6):807–811.doi:10.1021/jm00330a017.PMID 5885076.
  3. ^Havera, Herbert J.; Vidrio, H. (1979). "Derivatives of 1,3-disubstituted 2,4(1H,3H)-quinazolinediones as possible peripheral vasodilators or antihypertensive agents".Journal of Medicinal Chemistry.22 (12):1548–1550.doi:10.1021/jm00198a024.PMID 231656.
  4. ^Garcia, J. D.; Somanathan, R.; Rivero, I. A.; Aguirre, G.; Hellberg, L. H. (2000). "Synthesis of Deuterium-Labeled Antihypertensive 3-(4-Phenyl-1′-Piperazinyl)-Propyl-2,4-Quinazolinedione".Synthetic Communications.30 (15):2707–2711.doi:10.1080/00397910008086895.
  5. ^Li, Xin; Lee, Yong-Rok; Kim, Sung-Hong (2011). "Concise Synthesis of Pelanserine, Goshuyuamide II, and Wuchuyuamide II with Quinazolinedione Nuclei".Bulletin of the Korean Chemical Society.32 (9):3480–3482.doi:10.5012/bkcs.2011.32.9.3480.
  6. ^Cortez, R.; Rivero, I. A.; Somanathan, R.; Aguirre, G.; Ramirez, F.; Hong, E. (1991). "Synthesis of Quinazolinedione Using Triphosgene".Synthetic Communications.21 (2):285–292.doi:10.1080/00397919108020823.
  7. ^AT 269143B, "Verfahren zur Herstellung von neuen Chinazolindionderivaten und ihrer Säureadditionssalze bzw. ihrer entsprechenden Piperaziniumverbindungen [Process for the preparation of new quinazolinedione derivatives and their acid addition salts or their corresponding piperazinium compounds]", published 1969-03-10, assigned toMiles Laboratories, Inc. 
  8. ^Hayao Shin,U.S. patent 3,274,194 (1966 to Bayer Corp)
  9. ^Horacio Vidrio,U.S. patent 3,919,425 (1975 to Bayer Corp).


α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7


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