Design, synthesis and anti-tuberculosis activity of 1-adamantyl-3- heteroaryl ureas with improved in vitro pharmacokinetic properties

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 9, 2013, Pages 2587-2599

  North, E Jeffrey ^a   Scherman, Michael S ^b   Bruhn, David F ^a   Scarborough, Jerrod S ^a   Maddox, Marcus M ^a   Jones, Victoria ^b   Grzegorzewicz, Anna ^b   Yang, Lei ^a   Hess, Tamara ^b   Morisseau, Christophe ^c   Jackson, Mary ^b   McNeil, Michael R ^b   Lee, Richard E ^a  

^a ST JUDE CHILDREN S RESEARCH HOSPITAL   (United States)

^b Department of Environmental and Radiological Health Sciences   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Antibiotics; Antimicrobial agents; Medicinal chemistry; MmpL3; Transporter; Tuberculosis

Indexed keywords

1 (1 ADAMANTYL) 3 (2 OXAZOLYL)UREA; 1 (1 ADAMANTYL) 3 (2 PYRIDINYL)UREA; 1 (1 ADAMANTYL) 3 (2 PYRIMIDINYL)UREA; 1 (1 ADAMANTYL) 3 (3 PYRIDINYL)UREA; 1 (1 ADAMANTYL) 3 (4 PYRIDINYL)UREA; 1 (1 ADAMANTYL) 3 (4 PYRIMIDINYL)UREA; 1 (1 ADAMANTYL) 3 [3 (1,2,4 TRIAZOLYL)]UREA; 1 (1 ADAMANTYL) 3 [4 (1,3,5 TRIAZOLYL)]UREA; 1 (1 ADAMANTYL) 3 [4 [(4 AMINOPHENYL)SULFONYL]PHENYL]UREA; 1 (1 ADAMANTYL) 3 [4 [N (3,4 DIMETHYLISOXAZOL 5 YL)BENZENESULFONAMIDE ]]UREA; 1 (1 ADAMANTYL) 3 [4 [N (4 METHYLPYRIMIDIN 2 YL)BENZENESULFONAMIDE ]]UREA; 1 (1 ADAMANTYL) 3 [4 [N (4,5 DIMETHOXYISOXAZOL 2 YL)BENZENESULFONAMIDE ]]UREA; 1 (1 ADAMANTYL) 3 [4 [N (5 METHOXYISOXAZOL 3 YL)BENZENESULFONAMIDE ]]UREA; 1 (1 ADAMANTYL) 3 [4 [N (6 CHLOROPYRIDAZIN 3 YL)BENZENESULFONAMIDE ]]UREA; 1 (1 ADAMANTYL) 3 [4 [N (6 METHOXYPYRIDAZIN 3 YL)BENZENESULFONAMIDE ]]UREA; 1 ADAMANTYL 3 HETEROARYLUREA DERIVATIVE; CARRIER PROTEIN; EPOXIDE HYDROLASE; ISOXAZOLE DERIVATIVE; MMPL3 PROTEIN; MYCOLIC ACID; OXADIAZOLE DERIVATIVE; OXAZOLE DERIVATIVE; PHENYL GROUP; PYRAZOLE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; TRIAZINE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; CELL MEMBRANE; DRUG DESIGN; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; INHIBITION KINETICS; LIVER MICROSOME; MEMBRANE TRANSPORT; MINIMUM INHIBITORY CONCENTRATION; MOUSE; MYCOBACTERIUM; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTITUBERCULAR AGENTS; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ENZYME INHIBITORS; EPOXIDE HYDROLASES; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIACEAE; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; TUBERCULOSIS; UREA; VERO CELLS;

CORYNEBACTERINEAE;

EID: 84876129597     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.02.028     Document Type: Article

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