α- and β-hydrazino acid-based pseudopeptides inhibit the chymotrypsin-like activity of the eukaryotic 20S proteasome

European Journal of Medicinal Chemistry

Volumn 70, Issue , 2013, Pages 505-524

  Bordessa, Andrea ^a   Keita, Massaba ^a   Maréchal, Xavier ^b   Formicola, Lucia ^a   Lagarde, Nathalie ^a   Rodrigo, Jordi ^a   Bernadat, Guillaume ^a   Bauvais, Cyril ^a   Soulier, Jean Louis ^a   Dufau, Laure ^b   Milcent, Thierry ^a   Crousse, Benoit ^a   Reboud Ravaux, Michèle ^b   Ongeri, Sandrine ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

Chymotrypsin; Fluorine; Hydrazino acid; Proteasome inhibitors; Pseudopeptide; Trifluoromethyl

Indexed keywords

2 [3 [N [3 CARBAMOYL 2 [2 (2,5 DIMETHOXYPHENYL)ACETYLAMINO]PROPIONYL]HYDRAZINO] 4,4,4 TRIFLUORO BUTYRYLAMINO] 3 PHENYL PROPIONIC ACID METHYL ESTER; 2 [3 [N' (2 AMINO 6 BENZYLOXYCARBONYLAMINOHEXANOYL)HYDRAZINO]PROPIONYLAMINO] 3 PHENYL PROPIONIC ACID METHYL ESTER TRIFLUOROACETIC SALT; 2 [3 [N' (2 TERT BUTOXYCARBONYLAMINO 3 CARBAMOYL PROPRIONYL)HYDRAZINO] 4,4,4 TRIFLUORO BUTYRYLAMINO] 3 PHENYL PROPIONIC ACID METHYL ESTER; 2 [3 [N' [2 (2,5 DIMETHOXYPHENYL)ACETYL]HYDRAZINO] 4,4,4 TRIFLUORO BUTYRYLAMINO] 3 PHENYL PROPIONIC ACID METHYL ESTER; 2 [3 [N' [6 AMINO 2 [2 (2,5 DIMETHOXYPHENYL)ACETYLAMINO]HEXANOYL]HYDRAZINO] 4,4,4 TRIFLUORO BUTYRYLAMINO] 3 PHENYL PROPIONIC ACID METHYL ESTER TRIFLUOROACETIC SALT; 2 [3 [N' [6 BENZYLOXYCARBONYLAMINO 2 [2 (2,5 DIMETHOXYPHENYL)ACETYLAMINO]HEXANOYL]HYDRAZINO] 4,4,4 TRIFLUORO BUTYRYLAMINO] 3 PHENYL PROPIONIC ACID METHYL ESTER; 2 [3 [N' [6 BENZYLOXYCARBONYLAMINO 2 [2 (4 PHENOXYPHENYL)ACETYLAMINO]HEXANOYL]HYDRAZINO]PROPIONYLAMINO] 3 PHENYLPROPIONIC ACID METHYL ESTER; 3 [2 [6 AMINO 2 [[2 (2,5 DIMETHOXYPHENYL)ACETYL]AMINO]HEXANOYL]HYDRAZINO] 4,4,4 TRIFLUORO N [(3,4,5 TRIMETHYXOPHENYL)METHYL]BUTANAMIDE; 3 [2 [6 AMINO 2 [[2 (2,5 PHENOXYPHENYL)ACETYL]AMINO]HEXANOYL]HYDRAZINO] 4,4,4 TRIFLUORO N [(3,4,5 TRIMETHYXOPHENYL)METHYL]BUTANAMIDE; 9H FLUOREN 9 YLMETHYL N [5 (TERT BUTOXYCARBONYLAMINO) 1 [[[3 OXO 3 [(3,4,5 TRIMETHOXYPHENYL)METHYLAMINO]PROPYL]AMINO]CARBAMOYL]PENTYL]CARBAMATE; ALPHA AMINO ACID; CHYMOTRYPSIN; EUKARYOTIC 20S PROTEASOME; HYDRAZINE DERIVATIVE; METHYL 2 [3 [2 [6 (BENZYLOXYCARBONYLAMINO) 2 [[2 (2,5 DIMETHOXYPHENYL)ACETYL]AMINO]HEXANOYL]HYDRAZINO]PROPANOYLAMINO] 3 PHENYLPROPANOATE; METHYL 2 [3 [2 [6 AMINO 2 [[2 (2,5 DIMETHOXYPHENYL)ACETYL]AMINO]HEXANOYL]HYDRAZINO]PROPANOYLAMINO] 3 PHENYLPROPANOATE DIHYDROCHLORIDE SALT; METHYL 2 [3 [2 [6 AMINO 2 [[2 (3 PHENOXYPHENYL) ACETYL]AMINO]HEXANOYL]HYDRAZINO]PROPANOYLAMINO] 3 PHENYL PROPANOATE; N [1 [N [3 (3,4 DIMETHOXYPHENYL) 2 [2 (3 PHENOXYPHENYL)ACETYLAMINO]PROPIONYL]HYDRAZINOCARBONYLMETHYL] 2,2,2 TRIFLUOROETHYL]HYDRAZINECARBOXYLIC ACID TERT BUTYL ESTER; N' [1 [N' [3 (3,4 DIMETHOXYPHENYL) 2 (9H FLUOREN 9YLMETHOXYCARBONYLAMINO)PROPIONYL]HYDRAZINOCARBONYLMETHYL] 2,2,2 TRIFLUOROETHYL]HYDRAZINECARBOXYLIC ACID TERT BUTYL ESTER; N' [3 [N [3 (3,4 DIIMETHOXYPHENYL) 2 (9H FLUOREN 9YLMETHOXYCARBONYLAMINO)PROPIONYL]HYDRAZINO] 3 OXO 1 TRIFLUOROMETHYLPROPYL]HYDRAZINECARBOXYLIC ACID BENZYL ESTER; N' [3 [N' [2 AMINO 3 (3,4 DIMETHOXYPHENYL)PROPIONYL]HYDRAZINO] 3 OXO 1 TRIFLUOROMETHYLPROPYL]HYDRAZINECARBOXYLIC ACID BENZYL ESTER; N' [3 [N' [3 [3 (3,4 DIMETHYOXYPHENYL) 2 [2 (3 PHENOXYPHENYL)ACETYLAMINO]PROPIONYL]HYDRAZINO] 3 OXO 1 TRIFLUOROMETHYLPROPYL]HYDRAZINECARBOXYLIC ACID BENZYL ESTER; PROTEASOME; PROTEASOME INHIBITOR; PSEUDOPEPTIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; [2 CARBAMOYL 1 [N' [2,2,2 TRIFLUORO 1 [(3,4,5 TRIMETHOXYBENZYLCARBAMOYL)METHYL]ETHYL]HYDRAZINOCARBONYL]ETHYL]CARBAMIC ACID TERT BUTYL ESTER; [5 AMINO 5 [N' [2,2,2 TRIFLUORO 1 [(3,4,5 TRIMETHOXY BENZYL CARBAMOYL)METHYL]ETHYL]HYDRAZINOCARBONYL]PENTYL]CARBAMIC ACID BENZYL ESTER TRIFLUOROACETIC SALT; [5 TERT BUTOXYCARBONYLAMINO 5 [N' [2,2,2 TRIFLUORO 1 [(3,4,5 TRIMETHOXY BENZYLCARBAMOYL)METHYL]ETHYL]HYDRAZINOCARBONYL]PENTYL]CARBAMIC ACID BENZYL ESTER; [5 [2 (2,5 DIMETHOXYPHENYL) ACETYLAMINO] 5 [N' [2,2,2 TRIFLUORO 1 [(3,4,5 TRIMETHOXY BENZYLCARBAMOYL)METHYL]ETHYL]HYDRAZINOCARBONYL]PENTYL]CARBAMIC ACID BENZYL ESTER;

ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DIASTEREOISOMER; FEMALE; HUMAN; HUMAN CELL; HYDROGENOLYSIS; KINETICS; MOLECULAR MODEL; SYNTHESIS;

CHYMOTRYPSIN; FLUORINE; HYDRAZINO ACID; PROTEASOME INHIBITORS; PSEUDOPEPTIDE; TRIFLUOROMETHYL;

ANIMALS; CHYMOTRYPSIN; DOSE-RESPONSE RELATIONSHIP, DRUG; HYDRAZINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; PROTEASOME INHIBITORS; RABBITS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84886743109     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.09.059     Document Type: Article

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