Optimization and Structure-Activity Relationships of Phosphinic Pseudotripeptide Inhibitors of Aminopeptidases That Generate Antigenic Peptides

Journal of Medicinal Chemistry

Volumn 59, Issue 19, 2016, Pages 9107-9123

  Kokkala, Paraskevi ^a   Mpakali, Anastasia ^b   Mauvais, Francois Xavier ^c   Papakyriakou, Athanasios ^b   Daskalaki, Ira ^a   Petropoulou, Ioanna ^a   Kavvalou, Sofia ^a   Papathanasopoulou, Mirto ^a   Agrotis, Stefanos ^a   Fonsou, Theodora Markisia ^a   Van Endert, Peter ^c   Stratikos, Efstratios ^b   Georgiadis, Dimitris ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

^c INSERM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

(1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''R) 1'' AMINO 1'' OXO 3'' PHENYLPROPAN 2'' YL)CARBAMOYL] 4' METHYLPENTYL] PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''S) 1'' AMINNO 3'' (1H INDOL 3 YL) 1'' OXOPROPAN 2'' YL ]CARBAMOYL] 4' METHYLPENTYL]PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''S) 1'' AMINO 1'' OXO 3''PHENYLPROPAN 2'' YL)CARBAMOYL] 4' METHYLPENTYL]PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''S) 1'' AMINO 1'' OXOPROPAN 2'' YL)CARBAMOYL] 4' METHYLPENTYL]PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''S) 1'' AMINO 3'' (1H IMIDAZOL 4 YL) 1'' OXOPROPAN 2'' YL]CARBAMOYL] 4' METHYLPENTYL]PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''S) 1'' AMINO 3'' (4 HYDROXYPHENYL) 1'' OXOPROPAN 2'' YL]CARBAMOYL] 4' METHYLPENTYL]PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''S) 1'' AMINO 3'' HYDROXY 1'' OXOPROPAN 2'' YL]CARBAMOYL] 4' METHYLPENTYL]PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''S) 1'' AMINO 3'' PHENYLPROPYL)(HYDROXY)PHOSPHORYL]METHYL] 4' METHYL1 1'' OXOPROPAN 2'' YL]CARBAMOYL] 4' METHYLPENTANAMIDO] 5'' OXOPENTANOIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''S) 1'' AMINO 4'' METHYL 1'' OXOPROPAN 2'' YL)CARBAMOYL] 4' METHYLPENTYL]PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''S) 1'',6'' DIAMINO 1'' OXOHEXAN 2'' YL)CARBAMOYL] 4' METHYLPENTYL]PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 2' [((2''S) 2'' CARBAMOYLPYRROLIDINE 1'' CARBONYL) 4' METHYLPENTYL]PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 3' [((2''S) 1'' AMINO 1'' OXO 3'' PHENYLPROPAN 2'' YL)AMINO] 2' [[3 (2 METHOXYPHENYL)ISOXAZOL 5 YL]METHYL]PROPYL]PHOSPHINIC ACID; (1 AMINO 3 PHENYLPROPYL)[(2'S) 3' [((2''S) 1'' AMINO 1'' OXO 3'' PHENYLPROPAN 2'' YL)AMINO] 3' OXO 2' [(3 PHENYLISOXAZOL 5 YL)METHYL]PROPYL]PHOSPHINIC ACID; (2'S) 2' [[[1 [[(BENZYLOXY)CARBONYL]AMINO] 3 PHENYLPROPYL](HYDROXY)PHOSPHORYL]METHYL] 4' METHYLPENTANOIC ACID; (2'S) 2' [[[1 [[(TERT BUTOXY)CARBONYL]AMINO] 3 PHENYLPROPYL](HYDROXY)PHOSPHORYL]METHYL] 4' METHYLPENTANOIC ACID; 2' [[[(1 [[(TERT BUTOXY)CARBONYL]AMINO] 3 PHENYLPROPYL](HYDROXY)PHOSPHORYL]METHYL]PENT 4' YNOIC ACID; 3' (ADAMANTAN 1 YL) 2' [[[1 [[(TERT BUTOXY)CARBONYL]AMINO] 3 PHENYLPROPYL](HYDROXY)PHOSPHORYL]METHYL]PROPANOIC ACID; 3,3'' DICHLORO [1,1':3',1'' TERPHENYL] 5' CARBALDEHYDE; 5' (BROMOMETHYL) 1,1':3',1'' TERPHENYL; 5' (BROMOMETHYL) 3,3'' DICHLORO 1,1':3',1'' TERPHENYL; AMINOPEPTIDASE INHIBITOR; ETHYL 2 METHYLENE 4,4 DIPHENYLBUTANOATE; ETHYL 2 [(1,1':3',1'' TERPHENYL) 5' YLMETHYL]ACRYLATE; ETHYL 2 [[3,3'' DICHLORO (1,1':3',1'' TERPHENYL) 5 YL]METHYL]ACRYLATE; PHOSPHINIC ACID DERIVATIVE; PHOSPHINIC PSEUDOTRIPEPTIDE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; [1 [[(BENZYLOXY)CARBONYL]AMINO] 3 PHENYLPROPYL)[2' (ETHOXYCARBONYL) 4' METHYLPENTYL]PHOSPHINIC ACID; [1 [[(TERT BUTOXY)CARBONYL]AMINO] 3 PHENYLPROPYL][(2'S) 2' [((2''S) 1'' AMINO 1'' OXO 3'' PHENYLPROPAN 2'' YL) CARBAMOYL]PENT 4' YN 1' YL] PHOSPHINIC ACID; [1,1':3',1'' TERPHENYL] 5' CARBALDEHYDE; AMINOPEPTIDASE; CYSTYL AMINOPEPTIDASE; ERAP2 PROTEIN, HUMAN; LEUCYL-CYSTINYL AMINOPEPTIDASE; PEPTIDE; PHOSPHINE; PHOSPHINE DERIVATIVE;

ADAPTIVE IMMUNITY; ARTICLE; CONTROLLED STUDY; CROSS PRESENTATION; DENDRITIC CELL; DRUG EFFICACY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR MODEL; MOUSE; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; ANIMAL; ANTAGONISTS AND INHIBITORS; C57BL MOUSE; CELL LINE; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; HUMAN; IMMUNOLOGY;

AMINOPEPTIDASES; ANIMALS; CELL LINE; CYSTINYL AMINOPEPTIDASE; DENDRITIC CELLS; DRUG DESIGN; HUMANS; MICE, INBRED C57BL; MODELS, MOLECULAR; PEPTIDES; PHOSPHINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84991320833     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.6b01031     Document Type: Article

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