L-371,257

L-371,257
(IUPAC) ime
	1-[4-[(1-Acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]-4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidine
Klinički podaci
Identifikatori
CAS broj	162042-44-6
ATC kod	?
PubChem	6918320
Hemijski podaci
Formula	C28H33N3O6
Mol. masa	507.577 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C28H33N3O6/c1-19(32)29-15-11-22(12-16-29)37-23-7-8-24(26(17-23)35-2)27(33)30-13-9-21(10-14-30)31-25-6-4-3-5-20(25)18-36-28(31)34/h3-8,17,21-22H,9-16,18H2,1-2H3 ; Key: WDERJSQJYIJOPD-UHFFFAOYSA-N
Farmakoinformacioni podaci
Trudnoća	?
Pravni status

L-371,257 je lek koji se koristi u naučnim istraživanjima. On deluje kao selektivni antagonist oksitocinskog receptora sa preko 800x većom selektivnišću u odnosu na vazopresinske receptore.^[3] On je bio jedan od prvih nepeptidnih oksitocinskih antagonista.^[4]^[5]^[6]^[7] Ovaj materijal ima dobru oralnu bioraspoloživost i lošu penetraciju kroz krvno-moždanu barijeru što mu daje dobru perifernu selektivnost sa malim brojem centralnih nuspojava.^[8] Ovo jedinjenje potencialno može da nađe primenu u sprečavanju preranog porđaja.^[9]

Literatura

↑ 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. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ 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.
↑ Williams PD, Clineschmidt BV, Erb JM, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, Pettibone DJ i dr.. (1995). „1-(1-4-(N-acetyl-4-piperidinyl)oxy-2-methoxybenzoylpiperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist”. Journal of medicinal chemistry 38 (23): 4634–6. DOI:10.1021/jm00023a002. PMID 7473590.
↑ Bell IM, Erb JM, Freidinger RM, Gallicchio SN, Guare JP, Guidotti MT, Halpin RA, Hobbs DW i dr.. (1998). „Development of orally active oxytocin antagonists: studies on 1-(1-4-1-(2-methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy-2- methoxybenzoylpiperidin-4-yl)-1,4-dihydrobenzd1,3oxazin-2-one (L-372,662) and related pyridines”. Journal of medicinal chemistry 41 (12): 2146–63. DOI:10.1021/jm9800797. PMID 9622556.
↑ Kuo MS, Bock MG, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, Perlow DS, Pettibone DJ i dr.. (1998). „Nonpeptide oxytocin antagonists: potent, orally bioavailable analogs of L-371,257 containing a 1-R-(pyridyl)ethyl ether terminus”. Bioorganic & medicinal chemistry letters 8 (21): 3081–6. DOI:10.1016/S0960-894X(98)00568-X. PMID 9873680.
↑ Williams PD, Bock MG, Evans BE, Freidinger RM, Gallicchio SN, Guidotti MT, Jacobson MA, Kuo MS i dr.. (1999). „Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency”. Bioorganic & medicinal chemistry letters 9 (9): 1311–6. PMID 10340620.
↑ Wyatt PG, Allen MJ, Chilcott J, Foster A, Livermore DG, Mordaunt JE, Scicinski J, Woollard PM (2002). „Identification of potent and selective oxytocin antagonists. Part 1: indole and benzofuran derivatives”. Bioorganic & medicinal chemistry letters 12 (10): 1399–404. DOI:10.1016/S0960-894X(02)00159-2. PMID 11992786.
↑ Ring RH, Malberg JE, Potestio L, Ping J, Boikess S, Luo B, Schechter LE, Rizzo S i dr.. (2006). „Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications”. Psychopharmacology 185 (2): 218–25. DOI:10.1007/s00213-005-0293-z. PMID 16418825.
↑ Hawtin SR, Ha SN, Pettibone DJ, Wheatley M (2005). „A Gly/Ala switch contributes to high affinity binding of benzoxazinone-based non-peptide oxytocin receptor antagonists”. FEBS letters 579 (2): 349–56. DOI:10.1016/j.febslet.2004.10.108. PMID 15642343.

Spoljašnje veze

	Portal Medicina
	Portal Hemija

Šablon:Neuropeptidni ligandi

[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. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[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] Williams PD, Clineschmidt BV, Erb JM, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, Pettibone DJ i dr.. (1995). „1-(1-4-(N-acetyl-4-piperidinyl)oxy-2-methoxybenzoylpiperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist”. Journal of medicinal chemistry 38 (23): 4634–6. DOI:10.1021/jm00023a002. PMID 7473590.

[4] Bell IM, Erb JM, Freidinger RM, Gallicchio SN, Guare JP, Guidotti MT, Halpin RA, Hobbs DW i dr.. (1998). „Development of orally active oxytocin antagonists: studies on 1-(1-4-1-(2-methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy-2- methoxybenzoylpiperidin-4-yl)-1,4-dihydrobenzd1,3oxazin-2-one (L-372,662) and related pyridines”. Journal of medicinal chemistry 41 (12): 2146–63. DOI:10.1021/jm9800797. PMID 9622556.

[5] Kuo MS, Bock MG, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, Perlow DS, Pettibone DJ i dr.. (1998). „Nonpeptide oxytocin antagonists: potent, orally bioavailable analogs of L-371,257 containing a 1-R-(pyridyl)ethyl ether terminus”. Bioorganic & medicinal chemistry letters 8 (21): 3081–6. DOI:10.1016/S0960-894X(98)00568-X. PMID 9873680.

[6] Williams PD, Bock MG, Evans BE, Freidinger RM, Gallicchio SN, Guidotti MT, Jacobson MA, Kuo MS i dr.. (1999). „Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency”. Bioorganic & medicinal chemistry letters 9 (9): 1311–6. PMID 10340620.

[7] Wyatt PG, Allen MJ, Chilcott J, Foster A, Livermore DG, Mordaunt JE, Scicinski J, Woollard PM (2002). „Identification of potent and selective oxytocin antagonists. Part 1: indole and benzofuran derivatives”. Bioorganic & medicinal chemistry letters 12 (10): 1399–404. DOI:10.1016/S0960-894X(02)00159-2. PMID 11992786.

[8] Ring RH, Malberg JE, Potestio L, Ping J, Boikess S, Luo B, Schechter LE, Rizzo S i dr.. (2006). „Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications”. Psychopharmacology 185 (2): 218–25. DOI:10.1007/s00213-005-0293-z. PMID 16418825.

[9] Hawtin SR, Ha SN, Pettibone DJ, Wheatley M (2005). „A Gly/Ala switch contributes to high affinity binding of benzoxazinone-based non-peptide oxytocin receptor antagonists”. FEBS letters 579 (2): 349–56. DOI:10.1016/j.febslet.2004.10.108. PMID 15642343.

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