L-371,257
Chemical compound
- None
- 1-[4-[(1-Acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]-4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidine
- 162042-44-6 Y
- 6918320
- 2252
- 5293524 N
- ChEMBL24781 N
- DTXSID30426072
- Interactive image
- O=C1OCc3ccccc3N1C(CC4)CCN4C(=O)c2ccc(cc2OC)OC5CCN(C(C)=O)CC5
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 N
- Key:WDERJSQJYIJOPD-UHFFFAOYSA-N N
L-371,257 is a compound used in scientific research which acts as a selective antagonist of the oxytocin receptor with over 800x selectivity over the related vasopressin receptors.[1] It was one of the first non-peptide oxytocin antagonists developed,[2][3][4][5] and has good oral bioavailability, but poor penetration of the blood–brain barrier, which gives it good peripheral selectivity with few central side effects.[6] Potential applications are likely to be in the treatment of premature labour.[7]
See also
- Atosiban
- Barusiban
- Epelsiban
- L-368,899
- Retosiban
References
- ^ Williams PD, Clineschmidt BV, Erb JM, Freidinger RM, Guidotti MT, Lis EV, et al. (November 1995). "1-(1-[4-[(N-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]piperidin-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, et al. (June 1998). "Development of orally active oxytocin antagonists: studies on 1-(1-[4-[1-(2-methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy]-2- methoxybenzoyl]piperidin-4-yl)-1,4-dihydrobenz[d][1,3]oxazin-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, et al. (November 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, et al. (May 1999). "Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency". Bioorganic & Medicinal Chemistry Letters. 9 (9): 1311–6. doi:10.1016/S0960-894X(99)00181-X. PMID 10340620.
- ^ Wyatt PG, Allen MJ, Chilcott J, Foster A, Livermore DG, Mordaunt JE, et al. (May 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, et al. (April 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. S2CID 13647805.
- ^ Hawtin SR, Ha SN, Pettibone DJ, Wheatley M (January 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. S2CID 38088139.
- v
- t
- e
- Agonists: Peptide: Aspartocin
- Carbetocin
- Cargutocin
- Demoxytocin
- Lipo-oxytocin-1
- Merotocin
- Nacartocin
- Oxytocin
- PF-06478939
- PF-06655075 (PF1)
- TGOT
- Vasotocin (argiprestocin); Non-peptide: CA7
- LIT-001
- TC OT 39
- WAY-267464
- WJ0679
- Antagonists: Peptide: Atosiban
- Tocinoic acid; Non-peptide: Barusiban
- Cligosiban
- Epelsiban
- Erlosiban
- IX-01
- L-368,899
- L-371,257
- L-372,662
- Nolasiban
- Retosiban
- SSR-126768
- WAY-162720
- Catabolism inhibitors: Amastatin
- Bestatin (ubenimex)
- EDTA
- L-Methionine
- Leupeptin
- o-Phenanthroline
- Phosphoramidon
- Puromycin
V1A |
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V1B |
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V2 |
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Unsorted |
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- Carrier proteins: Neurophysin (I, II)