Pelanserin

Pelanserin
Nazivi
	Preferisani IUPAC naziv 3-[3-(4-Fenilpiperazin-1-il)propil]hinazolin-2,4(1H,3H)-dion
Identifikacija
CAS broj	2208-51-7 ;
3D model (Jmol)	interaktivna slika;
ChemSpider	58898;
PubChem C ID	65435;
UNII	6SNR96E409 ;
	SMILES C1CN(CCN1CCCN2C(=O)C3=CC=CC=C3NC2=O)C4=CC=CC=C4; ; ; ; ; ;
Svojstva
Hemijska formula	C21H24N4O2
Molarna masa	364,45 g·mol−1
	Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
	Reference infokutije

Pelanserin (TR2515) je antagonist 5-HT₂ i α₁-adrenergičkog receptora.^[3]

Sinteza

Reakcija između izatoičkog anhidrida (1) i 1-(3-aminopropil)-4-fenilpiperazina [20529-19-5] (2) sa fosgenom kompletira sintezu pelanserina (3).

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Ketanserin

Reference

^ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
^ Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.
^ 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. PMID 7493607. doi:10.1016/0014-2999(95)00074-u.
^ 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. PMID 5885076. doi:10.1021/jm00330a017.
^ Havera, Herbert J. (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.
^ 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.
^ 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.
^ 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.
^ 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 to Miles Laboratories, Inc.
^ Hayao Shin, U.S. Patent 3.274.194 (1966 to Bayer Corp).
^ Horacio Vidrio, U.S. Patent 3.919.425 (1975 to Bayer Corp).

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди

[2] Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.

[3] 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. PMID 7493607. doi:10.1016/0014-2999(95)00074-u.

[4] 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. PMID 5885076. doi:10.1021/jm00330a017.

[5] Havera, Herbert J. (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.

[6] 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.

[7] 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.

[8] 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.

[9] 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 to Miles Laboratories, Inc.

[10] Hayao Shin, U.S. Patent 3.274.194 (1966 to Bayer Corp).

[11] Horacio Vidrio, U.S. Patent 3.919.425 (1975 to Bayer Corp).

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Sinteza

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Reference

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