JNJ-7925476

JNJ-7925476
IUPAC име
	(6S,10bR)-6-(4-Etinilfenil)-1H,2H,3H,5H,6H,10bH-pirolo[2,1-a]izohinolin
Идентификатори
CAS број	129540-12-1 ; 109085-56-5
PubChem	CID 13903191
ChemSpider	23130640
UNII	VSM44B5G3G; IQ02SF57WP
ChEMBL	CHEMBL286312
Хемијски подаци
Формула	C20H19N
Моларна маса	273,38 g·mol−1
	SMILES C#CC1=CC=C(C=C1)[C@@H]2CN3CCC[C@@H]3C4=CC=CC=C24; ;
	InChI InChI=1S/C20H19N/c1-2-15-9-11-16(12-10-15)19-14-21-13-5-8-20(21)18-7-4-3-6-17(18)19/h1,3-4,6-7,9-12,19-20H,5,8,13-14H2/t19-,20+/m0/s1; Key:YPFCCQUUZJDQAM-VQTJNVASSA-N;

JNJ-7925476 je antidepresiv klase trostrukih inhibitora ponovnog uzimanja koji je otkrilo preduzeće Džonson & Džonson,^[1] ali nikada nije plasiran na tržište.

Ovaj molekul su prvi pripremili Brus E. Marjanof i saradnici tokom kasnih 1970-ih – 1980-ih.^[2]^[3]^[4] Struktura je pirolo izohinolinsko jezgro, sa benzhidrilnim motivom.

Osobine

JNJ-7925476 je organsko jedinjenje, koje sadrži 20 atoma ugljenika i ima molekulsku masu od 273,372 Da.

Osobina	Vrednost
Broj akceptora vodonika	1
Broj donora vodonika	0
Broj rotacionih veza	1
Particioni koeficijent^[5] (ALogP)	4,9
Rastvorljivost^[6] (logS, log(mol/L))	-4,5
Polarna površina^[7] (PSA, Å²)	3,2

Reference

^ Aluisio L, Lord B, Barbier AJ, Fraser IC, Wilson SJ, Boggs J, et al. (јун 2008). . „In-vitro and in-vivo characterization of JNJ-7925476, a novel triple monoamine uptake inhibitor”. European Journal of Pharmacology. 587 (1–3): 141—6. PMID 18499098. doi:10.1016/j.ejphar.2008.04.008.
^ Maryanoff BE, McComsey DF, Castanzo MJ, Setler PE, Gardocki JF, Shank RP, Schneider CR (август 1984). . „Pyrroloisoquinoline antidepressants. Potent, enantioselective inhibition of tetrabenazine-induced ptosis and neuronal uptake of norepinephrine, dopamine, and serotonin”. Journal of Medicinal Chemistry. 27 (8): 943—6. PMID 6747993. doi:10.1021/jm00374a001.
^ Maryanoff BE, McComsey DF, Gardocki JF, Shank RP, Costanzo MJ, Nortey SO, et al. (август 1987). . „Pyrroloisoquinoline antidepressants. 2. In-depth exploration of structure-activity relationships”. Journal of Medicinal Chemistry. 30 (8): 1433—54. PMID 3039136. doi:10.1021/jm00391a028.
^ Maryanoff BE, Vaught JL, Shank RP, McComsey DF, Costanzo MJ, Nortey SO (октобар 1990). . „Pyrroloisoquinoline antidepressants. 3. A focus on serotonin”. Journal of Medicinal Chemistry. 33 (10): 2793—7. PMID 2213832. doi:10.1021/jm00172a018.
^ Ghose, Arup K.; Viswanadhan, Vellarkad N.; Wendoloski, John J. (1998). . „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods”. The Journal of Physical Chemistry A. 102 (21): 3762—3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o.
^ Tetko, Igor V.; Tanchuk, Vsevolod Yu.; Kasheva, Tamara N.; Villa, Alessandro E. P. (2001). . „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Journal of Chemical Information and Computer Sciences. 41 (6): 1488—1493. PMID 11749573. doi:10.1021/ci000392t.
^ Ertl, Peter; Rohde, Bernhard; Selzer, Paul (2000). . „Fast Calculation of Molecular Polar Surface Area as a Sum of Fragment-Based Contributions and Its Application to the Prediction of Drug Transport Properties”. Journal of Medicinal Chemistry. 43 (20): 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

Literatura

Hardman JG, Limbird LE, Gilman AG (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10. изд.). New York: McGraw-Hill. ISBN 0071354697. doi:10.1036/0071422803.
Thomas L. Lemke; David A. Williams, ур. (2007). Foye's Principles of Medicinal Chemistry (6. изд.). Baltimore: Lippincott Willams & Wilkins. ISBN 0781768799.

Spoljašnje veze

JNJ-7925476

[Alusio-1] Aluisio L, Lord B, Barbier AJ, Fraser IC, Wilson SJ, Boggs J, et al. (јун 2008). . „In-vitro and in-vivo characterization of JNJ-7925476, a novel triple monoamine uptake inhibitor”. European Journal of Pharmacology. 587 (1–3): 141—6. PMID 18499098. doi:10.1016/j.ejphar.2008.04.008.

[2] Maryanoff BE, McComsey DF, Castanzo MJ, Setler PE, Gardocki JF, Shank RP, Schneider CR (август 1984). . „Pyrroloisoquinoline antidepressants. Potent, enantioselective inhibition of tetrabenazine-induced ptosis and neuronal uptake of norepinephrine, dopamine, and serotonin”. Journal of Medicinal Chemistry. 27 (8): 943—6. PMID 6747993. doi:10.1021/jm00374a001.

[3] Maryanoff BE, McComsey DF, Gardocki JF, Shank RP, Costanzo MJ, Nortey SO, et al. (август 1987). . „Pyrroloisoquinoline antidepressants. 2. In-depth exploration of structure-activity relationships”. Journal of Medicinal Chemistry. 30 (8): 1433—54. PMID 3039136. doi:10.1021/jm00391a028.

[serotonin-4] Maryanoff BE, Vaught JL, Shank RP, McComsey DF, Costanzo MJ, Nortey SO (октобар 1990). . „Pyrroloisoquinoline antidepressants. 3. A focus on serotonin”. Journal of Medicinal Chemistry. 33 (10): 2793—7. PMID 2213832. doi:10.1021/jm00172a018.

[5] Ghose, Arup K.; Viswanadhan, Vellarkad N.; Wendoloski, John J. (1998). . „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods”. The Journal of Physical Chemistry A. 102 (21): 3762—3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o.

[6] Tetko, Igor V.; Tanchuk, Vsevolod Yu.; Kasheva, Tamara N.; Villa, Alessandro E. P. (2001). . „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Journal of Chemical Information and Computer Sciences. 41 (6): 1488—1493. PMID 11749573. doi:10.1021/ci000392t.

[7] Ertl, Peter; Rohde, Bernhard; Selzer, Paul (2000). . „Fast Calculation of Molecular Polar Surface Area as a Sum of Fragment-Based Contributions and Its Application to the Prediction of Drug Transport Properties”. Journal of Medicinal Chemistry. 43 (20): 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

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