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'''L-371,257''' is a compound used in scientific research which acts as a selective [[Antagonist (pharmacology)|antagonist]] of the [[oxytocin receptor]] with over 800x selectivity over the related [[vasopressin receptor]]s.<ref>{{cite journal | last1 = Williams | first1 = PD | last2 = Clineschmidt | first2 = BV | last3 = Erb | first3 = JM | last4 = Freidinger | first4 = RM | last5 = Guidotti | first5 = MT | last6 = Lis | first6 = EV | last7 = Pawluczyk | first7 = JM | last8 = Pettibone | first8 = DJ | last9 = Reiss | first9 = DR | last10 = Veber | first10 = D. F. | title = 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 = Journal of Medicinal Chemistry | volume = 38 | issue = 23 | pages = 4634–6 | year = 1995 | pmid = 7473590 |name-list-format=vanc | doi=10.1021/jm00023a002| display-authors = 8 }}</ref> It was one of the first non-peptide oxytocin antagonists developed,<ref>{{cite journal | last1 = Bell | first1 = IM | last2 = Erb | first2 = JM | last3 = Freidinger | first3 = RM | last4 = Gallicchio | first4 = SN | last5 = Guare | first5 = JP | last6 = Guidotti | first6 = MT | last7 = Halpin | first7 = RA | last8 = Hobbs | first8 = DW | last9 = Homnick | first9 = CF | last10 = Kuo | first10 = Michelle S. | last11 = Lis | first11 = Edward V. | last12 = Mathre | first12 = David J. | last13 = Michelson | first13 = Stuart R. | last14 = Pawluczyk | first14 = Joseph M. | last15 = Pettibone | first15 = Douglas J. | last16 = Reiss | first16 = Duane R. | last17 = Vickers | first17 = Stanley | last18 = Williams | first18 = Peter D. | last19 = Woyden | first19 = Carla J. | title = 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 = Journal of Medicinal Chemistry | volume = 41 | issue = 12 | pages = 2146–63 | year = 1998 | pmid = 9622556 |name-list-format=vanc | doi = 10.1021/jm9800797 | display-authors = 8 }}</ref><ref>{{cite journal | last1 = Kuo | first1 = MS | last2 = Bock | first2 = MG | last3 = Freidinger | first3 = RM | last4 = Guidotti | first4 = MT | last5 = Lis | first5 = EV | last6 = Pawluczyk | first6 = JM | last7 = Perlow | first7 = DS | last8 = Pettibone | first8 = DJ | last9 = Quigley | first9 = AG | last10 = Reiss | first10 = Duane R. | last11 = Williams | first11 = Peter D. | last12 = Woyden | first12 = Carla J. | title = Nonpeptide oxytocin antagonists: potent, orally bioavailable analogs of L-371,257 containing a 1-R-(pyridyl)ethyl ether terminus | journal = Bioorganic & Medicinal Chemistry Letters | volume = 8 | issue = 21 | pages = 3081–6 | year = 1998 | pmid = 9873680 |name-list-format=vanc | doi = 10.1016/S0960-894X(98)00568-X | display-authors = 8 }}</ref><ref>{{cite journal | last1 = Williams | first1 = PD | last2 = Bock | first2 = MG | last3 = Evans | first3 = BE | last4 = Freidinger | first4 = RM | last5 = Gallicchio | first5 = SN | last6 = Guidotti | first6 = MT | last7 = Jacobson | first7 = MA | last8 = Kuo | first8 = MS | last9 = Levy | first9 = MR | last10 = Lis | first10 = Edward V. | last11 = Michelson | first11 = Stuart R. | last12 = Pawluczyk | first12 = Joseph M. | last13 = Perlow | first13 = Debra S. | last14 = Pettibone | first14 = Douglas J. | last15 = Quigley | first15 = Amy G. | last16 = Reiss | first16 = Duane R. | last17 = Salvatore | first17 = Christopher | last18 = Stauffer | first18 = Kenneth J. | last19 = Woyden | first19 = Carla J. | title = Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency | journal = Bioorganic & Medicinal Chemistry Letters | volume = 9 | issue = 9 | pages = 1311–6 | year = 1999 | pmid = 10340620 |name-list-format=vanc | doi=10.1016/S0960-894X(99)00181-X| display-authors = 8 }}</ref><ref>{{cite journal | last1 = Wyatt | first1 = PG | last2 = Allen | first2 = MJ | last3 = Chilcott | first3 = J | last4 = Foster | first4 = A | last5 = Livermore | first5 = DG | last6 = Mordaunt | first6 = JE | last7 = Scicinski | first7 = J | last8 = Woollard | first8 = PM | title = Identification of potent and selective oxytocin antagonists. Part 1: indole and benzofuran derivatives | journal = Bioorganic & Medicinal Chemistry Letters | volume = 12 | issue = 10 | pages = 1399–404 | year = 2002 | pmid = 11992786 |name-list-format=vanc | doi=10.1016/S0960-894X(02)00159-2}}</ref> and has good oral bioavailability, but poor penetration of the [[blood–brain barrier]], which gives it good peripheral selectivity with few central side effects.<ref>{{cite journal | last1 = Ring | first1 = RH | last2 = Malberg | first2 = JE | last3 = Potestio | first3 = L | last4 = Ping | first4 = J | last5 = Boikess | first5 = S | last6 = Luo | first6 = B | last7 = Schechter | first7 = LE | last8 = Rizzo | first8 = S | last9 = Rahman | first9 = Z | last10 = Rosenzweig-Lipson | first10 = Sharon | title = Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications | journal = Psychopharmacology | volume = 185 | issue = 2 | pages = 218–25 | year = 2006 | pmid = 16418825 |name-list-format=vanc | doi = 10.1007/s00213-005-0293-z | display-authors = 8 }}</ref> Potential applications are likely to be in the treatment of premature labour.<ref>{{cite journal | last1 = Hawtin | first1 = SR | last2 = Ha | first2 = SN | last3 = Pettibone | first3 = DJ | last4 = Wheatley | first4 = M | title = A Gly/Ala switch contributes to high affinity binding of benzoxazinone-based non-peptide oxytocin receptor antagonists | journal = FEBS Letters | volume = 579 | issue = 2 | pages = 349–56 | year = 2005 | pmid = 15642343 |name-list-format=vanc | doi = 10.1016/j.febslet.2004.10.108 }}</ref>
'''L-371257''' is a compound used in scientific research which acts as a selective [[Antagonist (pharmacology)|antagonist]] of the [[oxytocin receptor]] with over 800x selectivity over the related [[vasopressin receptor]]s.<ref>{{cite journal | last1 = Williams | first1 = PD | last2 = Clineschmidt | first2 = BV | last3 = Erb | first3 = JM | last4 = Freidinger | first4 = RM | last5 = Guidotti | first5 = MT | last6 = Lis | first6 = EV | last7 = Pawluczyk | first7 = JM | last8 = Pettibone | first8 = DJ | last9 = Reiss | first9 = DR | last10 = Veber | first10 = D. F. | title = 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 = Journal of Medicinal Chemistry | volume = 38 | issue = 23 | pages = 4634–6 | year = 1995 | pmid = 7473590 |name-list-format=vanc | doi=10.1021/jm00023a002| display-authors = 8 }}</ref> It was one of the first non-peptide oxytocin antagonists developed,<ref>{{cite journal | last1 = Bell | first1 = IM | last2 = Erb | first2 = JM | last3 = Freidinger | first3 = RM | last4 = Gallicchio | first4 = SN | last5 = Guare | first5 = JP | last6 = Guidotti | first6 = MT | last7 = Halpin | first7 = RA | last8 = Hobbs | first8 = DW | last9 = Homnick | first9 = CF | last10 = Kuo | first10 = Michelle S. | last11 = Lis | first11 = Edward V. | last12 = Mathre | first12 = David J. | last13 = Michelson | first13 = Stuart R. | last14 = Pawluczyk | first14 = Joseph M. | last15 = Pettibone | first15 = Douglas J. | last16 = Reiss | first16 = Duane R. | last17 = Vickers | first17 = Stanley | last18 = Williams | first18 = Peter D. | last19 = Woyden | first19 = Carla J. | title = 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 = Journal of Medicinal Chemistry | volume = 41 | issue = 12 | pages = 2146–63 | year = 1998 | pmid = 9622556 |name-list-format=vanc | doi = 10.1021/jm9800797 | display-authors = 8 }}</ref><ref>{{cite journal | last1 = Kuo | first1 = MS | last2 = Bock | first2 = MG | last3 = Freidinger | first3 = RM | last4 = Guidotti | first4 = MT | last5 = Lis | first5 = EV | last6 = Pawluczyk | first6 = JM | last7 = Perlow | first7 = DS | last8 = Pettibone | first8 = DJ | last9 = Quigley | first9 = AG | last10 = Reiss | first10 = Duane R. | last11 = Williams | first11 = Peter D. | last12 = Woyden | first12 = Carla J. | title = Nonpeptide oxytocin antagonists: potent, orally bioavailable analogs of L-371,257 containing a 1-R-(pyridyl)ethyl ether terminus | journal = Bioorganic & Medicinal Chemistry Letters | volume = 8 | issue = 21 | pages = 3081–6 | year = 1998 | pmid = 9873680 |name-list-format=vanc | doi = 10.1016/S0960-894X(98)00568-X | display-authors = 8 }}</ref><ref>{{cite journal | last1 = Williams | first1 = PD | last2 = Bock | first2 = MG | last3 = Evans | first3 = BE | last4 = Freidinger | first4 = RM | last5 = Gallicchio | first5 = SN | last6 = Guidotti | first6 = MT | last7 = Jacobson | first7 = MA | last8 = Kuo | first8 = MS | last9 = Levy | first9 = MR | last10 = Lis | first10 = Edward V. | last11 = Michelson | first11 = Stuart R. | last12 = Pawluczyk | first12 = Joseph M. | last13 = Perlow | first13 = Debra S. | last14 = Pettibone | first14 = Douglas J. | last15 = Quigley | first15 = Amy G. | last16 = Reiss | first16 = Duane R. | last17 = Salvatore | first17 = Christopher | last18 = Stauffer | first18 = Kenneth J. | last19 = Woyden | first19 = Carla J. | title = Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency | journal = Bioorganic & Medicinal Chemistry Letters | volume = 9 | issue = 9 | pages = 1311–6 | year = 1999 | pmid = 10340620 |name-list-format=vanc | doi=10.1016/S0960-894X(99)00181-X| display-authors = 8 }}</ref><ref>{{cite journal | last1 = Wyatt | first1 = PG | last2 = Allen | first2 = MJ | last3 = Chilcott | first3 = J | last4 = Foster | first4 = A | last5 = Livermore | first5 = DG | last6 = Mordaunt | first6 = JE | last7 = Scicinski | first7 = J | last8 = Woollard | first8 = PM | title = Identification of potent and selective oxytocin antagonists. Part 1: indole and benzofuran derivatives | journal = Bioorganic & Medicinal Chemistry Letters | volume = 12 | issue = 10 | pages = 1399–404 | year = 2002 | pmid = 11992786 |name-list-format=vanc | doi=10.1016/S0960-894X(02)00159-2}}</ref> and has good oral bioavailability, but poor penetration of the [[blood–brain barrier]], which gives it good peripheral selectivity with few central side effects.<ref>{{cite journal | last1 = Ring | first1 = RH | last2 = Malberg | first2 = JE | last3 = Potestio | first3 = L | last4 = Ping | first4 = J | last5 = Boikess | first5 = S | last6 = Luo | first6 = B | last7 = Schechter | first7 = LE | last8 = Rizzo | first8 = S | last9 = Rahman | first9 = Z | last10 = Rosenzweig-Lipson | first10 = Sharon | title = Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications | journal = Psychopharmacology | volume = 185 | issue = 2 | pages = 218–25 | year = 2006 | pmid = 16418825 |name-list-format=vanc | doi = 10.1007/s00213-005-0293-z | display-authors = 8 }}</ref> Potential applications are likely to be in the treatment of premature labour.<ref>{{cite journal | last1 = Hawtin | first1 = SR | last2 = Ha | first2 = SN | last3 = Pettibone | first3 = DJ | last4 = Wheatley | first4 = M | title = A Gly/Ala switch contributes to high affinity binding of benzoxazinone-based non-peptide oxytocin receptor antagonists | journal = FEBS Letters | volume = 579 | issue = 2 | pages = 349–56 | year = 2005 | pmid = 15642343 |name-list-format=vanc | doi = 10.1016/j.febslet.2004.10.108 }}</ref>


==See also==
==See also==
Line 56: Line 56:
* [[Barusiban]]
* [[Barusiban]]
* [[Epelsiban]]
* [[Epelsiban]]
* [[L-368,899]]
* [[L-368899]]
* [[Retosiban]]
* [[Retosiban]]


Revision as of 20:50, 19 May 2016

L-371,257
Identifiers
  • 1-[4-[(1-Acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]-4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H33N3O6
Molar mass507.577 g/mol g·mol−1
3D model (JSmol)
  • O=C1OCc3ccccc3N1C(CC4)CCN4C(=O)c2ccc(cc2OC)OC5CCN(C(C)=O)CC5
  • 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
 ☒NcheckY (what is this?)  (verify)

L-371257 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

References

  1. ^ Williams, PD; Clineschmidt, BV; Erb, JM; Freidinger, RM; Guidotti, MT; Lis, EV; Pawluczyk, JM; Pettibone, DJ; et al. (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. {{cite journal}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  2. ^ Bell, IM; Erb, JM; Freidinger, RM; Gallicchio, SN; Guare, JP; Guidotti, MT; Halpin, RA; Hobbs, DW; et al. (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. {{cite journal}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  3. ^ Kuo, MS; Bock, MG; Freidinger, RM; Guidotti, MT; Lis, EV; Pawluczyk, JM; Perlow, DS; Pettibone, DJ; et al. (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. {{cite journal}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  4. ^ Williams, PD; Bock, MG; Evans, BE; Freidinger, RM; Gallicchio, SN; Guidotti, MT; Jacobson, MA; Kuo, MS; et al. (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. {{cite journal}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  5. ^ 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. {{cite journal}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  6. ^ Ring, RH; Malberg, JE; Potestio, L; Ping, J; Boikess, S; Luo, B; Schechter, LE; Rizzo, S; et al. (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. {{cite journal}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  7. ^ 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. {{cite journal}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)

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