Synthesis and SAR study of novel 7-(pyridinium-3-yl)-carbonyl imidazo[5,1-b]thiazol-2-yl carbapenems

Maruyama, Takahisa; Kano, Yuko; Yamamoto, Yasuo; Kurazono, Mizuyo; Iwamatsu, Katsuyoshi; Atsumi, Kunio; Shitara, Eiki

doi:10.1016/j.bmc.2006.09.049

Cited by 17 publications

(3 citation statements)

References 3 publications

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“…A series of 1␤-methyl carbapenems having structural similarity to ME1036 showed potent activities against MRSA and PRSP, as well as against the gram-negative organism ampicillin-resistant, ␤-lactamase-negative Haemophilus influenzae (115).…”

Section: ␤-Lactam Antibiotics That Inhibit Pbp 2a: New Weapons In Thementioning

confidence: 99%

Molecular Basis and Phenotype of Methicillin Resistance in Staphylococcus aureus and Insights into New β-Lactams That Meet the Challenge

Llarrull

Fisher

Mobashery

2009

Antimicrob Agents Chemother

120

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Section: ␤-Lactam Antibiotics That Inhibit Pbp 2a: New Weapons In Thementioning

confidence: 99%

Molecular Basis and Phenotype of Methicillin Resistance in Staphylococcus aureus and Insights into New β-Lactams That Meet the Challenge

Llarrull

Fisher

Mobashery

2009

Antimicrob Agents Chemother

120

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“…Imidazole fused rings are members of an essential class of heterocycles that have gained significant attention because of their broad spectrum of applications − (Figure ). For example, imidazo[1,5- a ]pyridine derivatives display remarkable potential for biological applications in many disease indications, − such as Alzheimer’s disease, AIDS, and cancer. − Their derivatives have also been employed in N -heterocyclic carbene chemistry and as ligands in coordination chemistry .…”

Section: Introductionmentioning

confidence: 99%

Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp³)-H Amination–Cyclization under Aerobic Conditions

Peng,

Li,

Huang

et al. 2023

J. Org. Chem.

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An iron-catalyzed efficient C−H amination for the construction of imidazole-fused-ring systems was developed under aerobic conditions. Compared to previous studies, this work exhibited green features. The reaction was conducted in the green solvent anisole, with water as the only byproduct. Four C(sp 3 )−H bonds were cleaved and three C−N bonds were formed in this transformation. Imidazo[1,5-a]pyridine-, imidazo[5,1-b]oxazole-, imidazo[5,1-b]thiazole-, imidazo[1,5-a]pyrazine-, and imidazo-[1,5-a]imidazole-related N-heterocycles were obtained in acceptable-to-excellent yield.

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“…Diverse biological activities of β-lactam derivatives still inspire the interest of synthetic organic chemists in synthesis of new compounds containing the azetidinone fragment in their structures [1][2][3][4][5][6][7][8][9][10][11][12][13]. e β-lactams were firstly synthesized in 1907 by H. Staudinger via [2 + 2] cycloaddition reaction of Schiff base from aniline and benzaldehyde with diphenylketene [14,15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines

Kirillov

Nikiforova

Baibarodskikh

et al. 2019

Journal of Chemistry

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Interaction of the Reformatsky reagents, prepared from methyl 1-bromocyclopentane-1-carboxylate or methyl 1-bromocyclohexane-1-carboxylate, with N,N′-bis(arylmethylidene)benzidines has given rise to a set of intermediates as a result of nucleophilic addition to the C=N group of a substrate. Further intramolecular attack of the amide nitrogen atom onto the ester carbonyl group is responsible for the ring closure, which affords two series of spirocompounds: 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.4]octan-1-one) or 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.5]nonan-1-ones).

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Synthesis and SAR study of novel 7-(pyridinium-3-yl)-carbonyl imidazo[5,1-b]thiazol-2-yl carbapenems

Cited by 17 publications

References 3 publications

Molecular Basis and Phenotype of Methicillin Resistance in Staphylococcus aureus and Insights into New β-Lactams That Meet the Challenge

Molecular Basis and Phenotype of Methicillin Resistance in Staphylococcus aureus and Insights into New β-Lactams That Meet the Challenge

Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp³)-H Amination–Cyclization under Aerobic Conditions

Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines

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Synthesis and SAR study of novel 7-(pyridinium-3-yl)-carbonyl imidazo[5,1-b]thiazol-2-yl carbapenems

Cited by 17 publications

References 3 publications

Molecular Basis and Phenotype of Methicillin Resistance in Staphylococcus aureus and Insights into New β-Lactams That Meet the Challenge

Molecular Basis and Phenotype of Methicillin Resistance in Staphylococcus aureus and Insights into New β-Lactams That Meet the Challenge

Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp3)-H Amination–Cyclization under Aerobic Conditions

Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines

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Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp³)-H Amination–Cyclization under Aerobic Conditions