L-371,257

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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[1][2] 6918320
Hemijski podaci
Formula C28H33N3O6 
Mol. masa 507.577 g/mol
SMILES eMolekuli & PubHem
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[uredi - уреди | uredi izvor]

  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.  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; Reiss, 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. PMID 7473590. doi:10.1021/jm00023a002. 
  4. Bell, IM; Erb, JM; Freidinger, RM; Gallicchio, SN; Guare, JP; Guidotti, MT; Halpin, RA; Hobbs, DW; Homnick, CF (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. PMID 9622556. doi:10.1021/jm9800797. 
  5. Kuo, MS; Bock, MG; Freidinger, RM; Guidotti, MT; Lis, EV; Pawluczyk, JM; Perlow, DS; Pettibone, DJ; Quigley, AG (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. PMID 9873680. doi:10.1016/S0960-894X(98)00568-X. 
  6. Williams, PD; Bock, MG; Evans, BE; Freidinger, RM; Gallicchio, SN; Guidotti, MT; Jacobson, MA; Kuo, MS; Levy, MR (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. PMID 11992786. doi:10.1016/S0960-894X(02)00159-2. 
  8. Ring, RH; Malberg, JE; Potestio, L; Ping, J; Boikess, S; Luo, B; Schechter, LE; Rizzo, S; Rahman, Z (2006). "Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications". Psychopharmacology 185 (2): 218–25. PMID 16418825. doi:10.1007/s00213-005-0293-z. 
  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. PMID 15642343. doi:10.1016/j.febslet.2004.10.108. 

Spoljašnje veze[uredi - уреди | uredi izvor]


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