Synthesis of New Quinolone Antibiotics Utilizing Azetidine Derivatives Obtained from 1-Azabicyclo[1.1.0]butane

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概要

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• A series of 3-sulfenylazetidine derivatives 5a-f were synthesized via the ring-opening reactions of 1-azabicyclo[1.1.0]butane (ABB, 3) with thiols 4a-f in 50-92% yields. Treatment of ABB (3) with aromatic amines 9a-e and dibenzylamine (9f) in the presence of Mg(ClO_4)_2 afforded the corresponding 3-aminoazetidine derivatives 10a-f in 24-65% yields. N-Benzyl-3-bromoazetidine (13), which was obtained by the reaction of ABB (3) with benzyl bromide, gave 3-aliphatic amino-substituted azetidine derivatives 15a, b. Novel fluoroquinolones 7a-f, 11a-f, 16a, b and 25a-c were obtained by the introduction of these azetidine derivatives into the C7 position of a quinolone nucleus 6 and N1-heterocyclic quinolones 21a-c in 21-83% yields. Some of them exhibited a greater antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) in comparison with that of clinically used fluoroquinolone, levofloxacin (LVFX).

• 社団法人日本薬学会の論文
• 2008-03-01

著者

• SHIRO Motoo

  Rigaku Corporation X-ray Research Laboratory

• Shiro Motoo

  Rigaku Corporation

• Shiro M

  Rigaku Corp. Tokyo

• Hayashi Kazuhiko

  College of Pharmacy, Kinjo Gakuin University

• Sano Shigeki

  Graduate School of Pharmaceutical Sciences, The University of Tokushima

• Nagao Yoshimitsu

  Graduate School of Pharmaceutical Sciences, The University of Tokushima

• IKEE Yoshifumi

  Graduate School of Pharmaceutical Sciences, The University of Tokushima

• HASHIMOTO Kana

  Graduate School of Pharmaceutical Sciences, The University of Tokushima

• KAMINO Mai

  Graduate School of Pharmaceutical Sciences, The University of Tokushima

• NAKASHIMA Masaaki

  Graduate School of Pharmaceutical Sciences, The University of Tokushima

• Kamino Mai

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• 佐野 茂樹

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• 佐野 茂樹

  徳島大学薬学部

• Sano Shigeki

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• Hayashi Kyoko

  Faculty Of Medicine Toyama Medical And Pharmaceutical University

• Ikee Yoshifumi

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• 長尾 善光

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• 長尾 善光

  徳島大学薬学部

• Nagao Yoshimitsu

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• Nagao Y

  Faculty Of Pharmaceutical Sciences The University Of Tokushima

• Nagao Yoshimitsu

  Faculity Of Pharmaceutical Sciences The University Of Tokushima

• Nakashima Masaaki

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• Shiro M

  Rigaku Corporation

• Suzuki Mitsuko

  Institute For Chemical Research Kyoto University

• Masuoka S

  Takara Agri Co. Ltd.

• Shiro Motoo

  Rigaku Co.

• Shiro Motoo

  Shionogi Research Laboratry Shionogi & Co. Ltd.

• Hayashi K

  Graduate School Of Medicine And Pharmaceutical Sciences For Research University Of Toyama

• Mito S

  Institute For Chemical Research Kyoto University

• Hashimoto Kana

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

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