123054-36-4Relevant academic research and scientific papers
studies on anti-helicobacter pylori agents. Part 2: New cephem derivatives
Yoshida, Yoshiki,Matsuda, Keiji,Sasaki, Hiroshi,Matsumoto, Yoshimi,Matsumoto, Satoru,Tawara, Shuichi,Takasugi, Hisashi
, p. 2317 - 2335 (2007/10/03)
The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of cephem derivatives are described. Introduction of thio-heterocyclic groups containing N- and S-atoms to the 3-position and phenyl or thienyl acetamido groups to the 7-position of the cephem nucleus dramatically improved the activity. From this series of derivatives, compound 13i was found to have extremely potent in vitro anti-H. pylori activity, superior therapeutic efficacy compared to AMPC and CAM, no cross-resistance between CAM or MNZ and low potential for causing diarrhea due to instability to β-lactamase. Copyright (C) 2000 Elsevier Science Ltd.
Novel cephalosporin derivatives possessing a bicyclic heterocycle at the 3-Position. Part I: Synthesis and biological activities of 3-(benzothiazol-2-yl)thiocephalosporin derivatives, CP0467 and related compounds
Tsushima, Masaki,Iwamatsu, Katsuyoshi,Tamura, Atsushi,Shibahara, Seiji
, p. 1009 - 1017 (2007/10/03)
A series of cephalosporin derivatives with various bicyclic heterocycles at the C-3 position was synthesized and evaluated for antibacterial activity. Among them CP0467 (3a) showed excellent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) (MIC90=6.25μg/mL), and extremely high affinity for the penicillin binding protein 2' of MRSA (I50=0.49μg/mL). Furthermore, 3a showed a long-acting pharmacokinetic profile in mice (AUC(∞)=482.3μg/h/mL and T(1/2)=1.9h). Copyright (C) 1998 Elsevier Science Ltd.
A Novel Approach to Cephalosporins From Allenylazetidinones: A New Cyclization Strategy via Tandem Cuprate Addition-Sulfenylation
Kant, Joydeep,Roth, Jeanine A.,Fuller, Carl E.,Walker, Donald G.,Benigni, Daniel A.,Farina, Vittorio
, p. 4956 - 4966 (2007/10/02)
An efficient approach to the synthesis of 3-substituted cephems bearing carbon-based substituents of choice at the C(3) position from inexpensive penicillins is described.The strategy involves the synthesis of an allenylazetidinone from penicillin sulfoxide followed by the addition of an organocuprate at low temperature.Organocuprates undergo 1,4-conjugate addition at the central allenic carbon of the allenylazetidinone to form a carbon-carbon bond which is followed by ring closure via an intramolecular sulfenylation reaction.The chemistry has been applied to the synthesis of a variety of 3-substituted cephems bearing substituents such as alkyl, cycloalkyl, aryl, alkenyl, and allyl.Precursors to the synthesis of important antibiotics, i.e.Cefadroxil, Cefixime, and Cefzil, are also available from this novel approach.The methodology is not limited to carbon-based 3-substituted cephems, but provides access to some 3-norcephalosporins as well.
