Synthesis and in vitro/in vivo antibacterial activity of oxazolidinones having thiocarbamate at C-5 on the A-ring and an amide- or urea-substituted [1,2,5]triazepane or [1,2,5]oxadiazepane as the C-ring

European Journal of Medicinal Chemistry

Volumn 69, Issue , 2013, Pages 262-277

  Suzuki, Hideyuki ^a   Utsunomiya, Iwao ^a   Shudo, Koichi ^a   Fukuhara, Norio ^b   Iwaki, Tsutomu ^b   Yasukata, Tatsuro ^b  

^a Kawasaki   (Japan)

^b SHIONOGI AND CO LTD   (Japan)

Author keywords

1,2,5 Oxadiazepane; 1,2,5 Triazepane; Antibacterial; Methicillin resistant Staphylococcus aureus; Oxazolidinone

Indexed keywords

3 [4 (1 ACETYL[1,2,5]TRIAZEPAN 5 YL) 3,5 DIFLUOROPHENYL] 5 (1,2,3 TRIAZOL 1 YLMETHYL) OXAZOLIDIN 2 ONE; 3 [4 (1 DIFLUOROACETYL[1,2,5]TRIAZEPAN 5 YL) 3,5 DIFLUOROPHENYL] 5 (1,2,3 TRIAZOL 1 YLMETHYL) OXAZOLIDIN 2 ONE; 3 [4 (1 FORMYL[1,2,5]TRIAZEPAN 5 YL) 3,5 DIFLUOROPHENYL] 5 (1,2,3 TRIAZOL 1 YLMETHYL) OXAZOLIDIN 2 ONE; 3 [4 (10 OXO 5,6,8,9 TETRAHYDRO 10H 4,4B,7,9ATETRAAZABENZO[A]AZULEN 7 YL) 3 FLUOROPHENYL] 5 (1,2,3 TRIAZOL 1 YLMETHYL) OXAZOLIDIN 2 ONE; 3 [4 (10 OXO 5,6,8,9 TETRAHYDRO 10H 4,4B,7,9ATETRAAZABENZO[A]AZULEN 7 YL) 3,5 DIFLUOROPHENYL] 5 (1,2,3 TRIAZOL 1 YLMETHYL) OXAZOLIDIN 2 ONE; 3 [4 (2 AMINO 10 OXO 5,6,8,9 TETRAHYDRO 10H 4,4B,7,9ATETRAAZABENZO[A]AZULEN 7 YL) 3,5 DIFLUOROPHENYL] 5 (1,2,3 TRIAZOL 1 YLMETHYL) OXAZOLIDIN 2 ONE; 5 (ISOXAZOL 3 YLAMINOMETHYL) 3 (3,5 DIFLUORO 4 (1 FORMYL [1,2,5]TRIAZEPAN 5 YL)OXAZOLIDIN 2 ONE; 5 (ISOXAZOL 3 YLAMINOMETHYL) 3 [3,5 DIFLUORO 4 (1 DIFLUOROACETYL)[1,2,5]TRIAZEPAN 5 YL)PHENYL]OXAZOLIDIN 2 ONE; AMIDE; ANTIINFECTIVE AGENT; LINEZOLID; N [[3 [3 FLUORO 4 (1 FORMYL[1,2,5]TRIAZEPAN 5 YL) PHENYL]-2-OXO-5-OXAZOLIDINYL]METHYL] O METHYTHIOCARBAMATE; N [[3 [3 FLUORO 4 (10 OXO 5,6,8,9 TETRAHYDRO 10H 4,4B,7,9A TETRAAZABENZO[A]AZULEN 7 YL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]ACETAMIDE; N [[3 [3,3 DIFLUORO 4 (2 ACETYL[1,2,5]OXADIAZEPAN 5 YL) PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETAMIDE; N [[3 [3,3 FLUORO 4 (1 ACETYL[1,2,5]TRIAZEPAN 5 YL) PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL] O METHYLTHIOCARBAMATE; N [[3 [3,3 FLUORO 4 (1 CARBAMOYL [1,2,5]TRIAZEPAN 5 YL) PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETAMIDE; N [[3 [3,3 FLUORO 4 (1 DIFLUOROACETYL[1,2,5]TRIAZEPAN 5 YL) PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL] O METHYLTHIOCARBAMATE; N [[3 [3,3 FLUORO 4 (10 OXO 5,6,8,9 TETRAHYDRO 10H 4,4B,7,9A TETRAAZABENZO[A]AZULEN 7 YL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL] O METHYLTHIOCARBAMATE; N [[3 [3,5 DIFLUORO 4 (1 ACETYL[1,2,5]TRIAZEPAN 5 YL) PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL] O METHYLTHIOCARBAMATE; N [[3 [3,5 DIFLUORO 4 (1 CARBAMOYL [1,2,5]TRIAZEPAN 5 YL) PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETAMIDE; N [[3 [3,5 DIFLUORO 4 (10 OXO 5,6,8,9 TETRAHYDRO 10H 4,4B,7,9A TETRAAZABENZO[A]AZULEN 7 YL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL] O METHYLTHIOCARBAMATE; N [[3 [3,5 DIFLUORO 4 (10 OXO 5,6,8,9 TETRAHYDRO 10H 4,4B,7,9A TETRAAZABENZO[A]AZULEN 7 YL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]ACETAMIDE; N [[3 [3,5 DIFLUORO 4 (2 ACETYL[1,2,5]OXADIAZEPAN 5 YL) PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]ACETAMIDE; N [[3 [3,5 DIFLUORO 4 (2 AMINO 10 OXO 5,6,8,9 TETRAHYDRO 10H 4,4B,7,9A TETRAAZABENZO[A]AZULEN 7 YL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]ACETAMIDE; N [[3 [3,5 DIFLUORO 4 (2 BROMO 10 OXO 5,6,8,9 TETRAHYDRO 10H 4,4B,7,9A TETRAAZABENZO[A]AZULEN 7 YL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]ACETAMIDE; N [[3 [3,5 DIFLUORO 4 (2 CHLORO 10 OXO 5,6,8,9 TETRAHYDRO 10H 4,4B,7,9A TETRAAZABENZO[A]AZULEN 7 YL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]ACETAMIDE; OXAZOLIDINONE DERIVATIVE; THIOCARBAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; UREA;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; DRUG SYNTHESIS; ENZYME ACTIVITY; IN VITRO STUDY; IN VIVO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; THERAPY EFFECT;

ANTIBACTERIAL; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; OXAZOLIDINONE; [1,2,5]OXADIAZEPANE; [1,2,5]TRIAZEPANE;

AMIDES; ANTI-BACTERIAL AGENTS; CYTOCHROME P-450 ENZYME SYSTEM; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; MICROBIAL SENSITIVITY TESTS; MONOAMINE OXIDASE; OXAZEPINES; OXAZOLIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP; THIOCARBAMATES; UREA;

EID: 84883678974     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.08.002     Document Type: Article

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