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Bioorganic and Medicinal Chemistry Letters
Volumn 5, Issue 2, 1995, Pages 145-150
Non-peptidic inhibitors of neutral endopeptidase 24.11 1. Discovery and optimization of potency
Author keywords

[No Author keywords available]
Indexed keywords

2 (4 BIPHENYLYL) 1 (1H TETRAZOL 5 YL)ETHYLAMINOMETHYLPHOSPHONIC ACID; CGS 24592; DIPEPTIDYL CARBOXYPEPTIDASE; ENDOTHELIN CONVERTING ENZYME; ENZYME INHIBITOR; MEMBRANE METALLOENDOPEPTIDASE; THERMOLYSIN; UNCLASSIFIED DRUG;
EID: 0028840084     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(94)00474-T     Document Type: Article
Times cited : (72)
References (23)
  • 5
    • 84916562476 scopus 로고    scopus 로고
    • 50 = 5 and 40 nM, respectively).
  • 6
    • 0000444481 scopus 로고
    • 2OTf, and ref.4, followed by sequential deprotections of the carboxylic (NaOH) and the phosphonic acids (TMSBr or HBr / AcOH)
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1477
    • Phillion1    Andrew2
  • 7
    • 84916562475 scopus 로고    scopus 로고
    • (S)-Dimethylphosphonomethyl-4(phenyl)phenylalanine (ref.4) was esterified with diazomethane and treated with ammonia in methanol to provide, after deprotection of the phosphonic acid (HBr / AcOH), amide 4.
  • 8
    • 84916562474 scopus 로고    scopus 로고
    • Coupling of (S)-N-(dimethylphosphonomethyl)-4(phenyl)phenylalanine with N-benzylamine (EDC / HOBt) afforded the precursor to 5.
  • 9
    • 33751391090 scopus 로고
    • The biarylalanine methyl esters used in the preparation of 7, 8 and 9 were synthesized by Suzuki biaryl coupling of the corresponding o-, m- or p- N-tBOC tyrosine triflate methyl ester with phenyl or tolyl boronic acid
    • (1992) J. Org. Chem. , vol.57 , pp. 379
    • Shieh1    Carlson2
  • 10
    • 33845185214 scopus 로고
    • 2COOtBu, under O'Donnell's conditions, led to the desired optically pure (S)-(4-phenyl-3-methoxy)phenylalanine used in the preparation of 10
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2353
    • O'Donnell1    Bennett2    Wu3
  • 11
    • 84986457308 scopus 로고
    • An Efficient Synthesis of 3-Heteroarylpyridines via Diethyl-(3-pyridyl)-borane
    • Palladium-catalyzed coupling between diethyl(3-pyridyl)borane and (S)-N-tBOC tyrosine triflate methyl ester produced the desired (S)-4-(3-pyridyl)phenylalanine precursor to 11
    • (1984) Synthesis , pp. 936
    • Ishikura1    Kamada2    Terashima3
  • 12
    • 84916562473 scopus 로고    scopus 로고
    • 3) to prevent diketopiperazine formation. The carboxylic acid was liberated (NaOH), activated as a mixed anhydride (iBuOCOCl / NMM), and coupled with 5-aminotetrazole. Hydrogenolysis of the Cbz group gave the desired phosphonate precursor of 12.
  • 13
    • 0000348708 scopus 로고
    • A New Route to 2-Aminoalkanephosphonic Acids
    • 3CN) of diethylphosphonoacetaldehyde, with (S)-(4-phenyl)phenylalanine methyl ester was used to prepare the β-amino phosphonate moiety in 13
    • (1978) Synthetic Communications , vol.8 , pp. 335
    • Varlet1    Collignon2    Savignac3
  • 14
    • 0023804445 scopus 로고
    • Design of novel inhibitors of aminopeptidases. Synthesis of peptide-derived diamino thiols and sulfur replacement analogs of bestatin
    • (S)-N-tBOC-(4-phenyl)phenylalanine was activated as a mixed anhydride (iBuOCOCl / NMM) and treated with diazomethane. Wolff rearrangement of the diazoketone PhCOOAg / MeOH / TEA, produced the chiral β-amino ester used for the synthesis of 14
    • (1988) Journal of Medicinal Chemistry , pp. 2199
    • Gordon1    Godfrey2    Delaney3    Asaad4    Von Langen5    Cushman6
  • 15
    • 84916562472 scopus 로고    scopus 로고
    • 2 / Pd-C) of the double bond gave the saturated amino ester used in the synthesis of 15.

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