Structure activity studies of the serine-AIB dipeptide domain in 2,3-dihydroisothiazole based growth hormone secretagogues

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 24, 2005, Pages 6748-6762

  Evers, Britta ^a   Ruehter, Gerd ^a   Berg, Martina ^a   Dodge, Jeffrey A ^b   Hankotius, Dirk ^a   Hary, Ulrike ^a   Jungheim, Louis N ^b   Mest, Hans Juergen ^a   De La Nava, Eva Maria Martin ^a   Mohr, Michael ^a   Muehl, Brian S ^b   Petersen, Soenke ^a   Sommer, Birgit ^a   Riedel Herold, Grit ^a   Tebbe, Mark J ^b   Thrasher, Kenneth J ^b   Voelkers, Silke ^a  

^a LILLY DEUTSCHLAND GMBH   (Germany)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

Growth hormone; Growth hormone secretagogue

Indexed keywords

2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2 CARBOXAMIDOPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2 CHLORO 3,6 DIFLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2 CHLORO 4 FLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2 CHLORO 6 FLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2 CYANOPHENYL)METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2 FLUOROPHENYL)METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2 METHYLPHENYL)METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2 TRIFLUOROMETHYLPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2,3 DICHLOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2,3 DIFLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2,3,5 TRIFLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2,3,6 TRIFLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2,4 DIFLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2,4,5 TRIFLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2,5 DIFLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2,6 DICHLOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (2,6 DIFLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (3 FLUOROPHENYL)METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (3,5 DIFLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (4 CHLORO 2 FLUOROPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (4 CHLOROPHENYL)METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (4 CYANOPHENYL)METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (4 FLUOROPHENYL)METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (4 TRIFLUOROMETHOXYPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; 2 [2 (2 AMINO 2 METHYLPROPIONYLAMINO)] 3 (4 TRIFLUOROMETHYLPHENYL) METHOXYPROPIONIC ACID N [5 (4 CHLOROPHENYL) 3,3 DIMETHYL 1,1 DIOXO 2,3 DIHYDROISOTHIAZOL 4 YLMETHYL] N ETHYLAMIDE; DIPEPTIDE; GROWTH HORMONE SECRETAGOGUE; SERINE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

AMINOBUTYRIC ACIDS; ANIMALS; CARBOXYLIC ACIDS; CELLS, CULTURED; CROSS-LINKING REAGENTS; DIPEPTIDES; GROWTH HORMONE; MALE; METHYLATION; MOLECULAR STRUCTURE; PHENANTHRENES; PITUITARY GLAND; RATS; RATS, SPRAGUE-DAWLEY; SERINE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 27644569574     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.07.070     Document Type: Article

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