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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 21
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Original Articles

Synthesis, Characterization, and Antimicrobial Evaluation of Quinoline-Oxadiazole–Based Azetidinone Derivatives

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Pages 3230-3241 | Received 25 Jan 2011, Published online: 17 Aug 2012

REFERENCES

  • Wakelin , I. ; Waring , M. J. DNA intercalating agents . In Comprehensive Medicinal Chemistry ; P. G. Sammes (Ed.); Pergamon : Oxford , UK , 1990 ; vol. 2 , p. 725 .
  • Cheng , C. C. ; Zee-Cheng , R. Y. K. In Progress in Medicinal Chemistry ; G. P. Ellis and G. B. West (Eds.); Elsevier : Amsterdam , 1983 ; p. 83 .
  • Murray , V. A. Survey of the Sequence-Specific Interactions of Damaging Agents with DNA: Emphasis on Antitumoral Agents ; Academic Press : New York , 2000 ; p. 367 .
  • Lown , J. W. , (Ed.); Anthracycline- and Antracenedione-Based Anticancer Agents: Bioactive Molecules ; Elsevier : Amsterdam , 1988 ; vol. 8 .
  • Krapcho , A. P. ; Petry , M. E. ; Getahun , Z. ; Landi , J. J. ; Stallman , J. ; Polsenberg , J. F. ; Gallagher , C. E. ; Maresch , M. E. ; Hacker , M. P. ; Giuliani , F. C. ; Beggiolin , G. ; Pezzoni , G. ; Menta , E. ; Manzotti , C. ; Oliva , A. ; Spineli , S. ; Tognella , S. 6,9-Bis[(aminoalkyl)amino]benzo[g]isoquinoline-5,10-diones: A novel class of chromophore-modified antitumor anthracene-9,10-diones: Synthesis and antitumor evaluations. J. Med. Chem. 1994, 37, 828–837.
  • Krapcho , A. P. ; Petry , M. E. ; Hacker , M. P. Heterosubstituted anthracene-9,10-dione analogs: The synthesis and antitumor evaluation of 5,8-bis[(aminoalkyl)-amino]naphtho[2,3-b]thiophene-4,9-diones . J. Med. Chem. 1990 , 33 , 2651 – 2655 .
  • Krapcho , A. P. ; Menta , E. ; Oliva , A. ; Di Domenico , R. ; Fiocchi , L. ; Maresch , M. E. ; Gallagher , C. E. ; Hacker , M. P. ; Beggiolin , G. ; Giuliani , F. C. ; Pezzoni , G. ; Spineli , S. Synthesis and antitumor evaluation of 2,5-disubstituted-indazolo[4,3-gh]isoquinolin-6(2 h)-ones (9-aza-anthrapyrazoles) . J. Med. Chem. 1998 , 41 , 5429 – 5444 .
  • Tully , W. R. ; Gardner , C. R. ; Gillespie , R. J. ; Westwood , R. 2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors . J. Med. Chem. 1991 , 34 , 2060 – 2067 .
  • Manjunatha , K. ; Poojary , B. ; Lobo , P. L. ; Fernandes , J. ; Kumari , N. S. Synthesis and biological evaluation of some 1,3,4-oxadiazole derivatives . Eur. J. Med. Chem. 2010 , 45 , 5225 – 5233 .
  • Holla , B. S. ; Gonsalves , R. ; Shenoy , S. Synthesis and antibacterial studies of a new series of 1,2-bis(1,3,4-oxadiazol-2-yl)ethanes and 1,2-bis(4-amino-1,2,4-triazol-3-yl)ethanes . Eur. J. Med. Chem. 2000 , 35 , 267 – 271 .
  • Vardan , S. ; Mookherjee , S. ; Eich , R. Effects of tiodazosin, a new antihypertensive: Hemodynamics and clinical variables . Clin. Pharm. Ther. 1983 , 34 , 290 – 296 .
  • Schlecker , R. ; Thieme , P. C. The synthesis of antihypertensive 3-(1,3,4-oxadiazol-2-yl)phenoxypropanolahines . Tetrahedron 1988 , 44 , 3289 – 3294 .
  • Johns , B. A. Naphthyridine integrase inhibitors. PCT Int. Appl. WO Patent 101512, 2004.
  • Baxendale , I. R. ; Ley , S. V. ; Martinelli , M. The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating . Tetrahedron 2005 , 61 , 5323 – 5349 .
  • Coppo , F. T. ; Evans , K. A. ; Graybill , T. L. ; Burton , G. Efficient one-pot preparation of 5-substituted-2-amino-1,3,4-oxadiazoles using resin-bound reagents . Tetrahedron Lett. 2004 , 45 , 3257 – 3260 .
  • Brain , C. T. ; Paul , J. M. ; Loong , Y. ; Oakley , P. J. Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions . Tetrahedron Lett. 1999 , 40 , 3275 – 3278 .
  • Wang , Y. ; Sauer , D. R. ; Djuric , S. W. A simple and efficient one-step synthesis of 1,3,4-oxadiazoles utilizing polymer-supported reagents and microwave heating . Tetrahedron Lett. 2006 , 47 , 105 – 108
  • Abell , A. D. ; Oldham , M. D. Leucine-phenylalanine dipeptide-based N-mesyloxy-succinimides: Synthesis of all four stereoisomers and their assay against serine proteases . Bioorg. Med. Chem. Lett. 1999 , 9 , 497 – 500 .
  • Annunziata , R. ; Benaglia , M. ; Cinquini , M. ; Cozzi , F. ; Puglisi , A. Efficient and highly stereoselective synthesis of a β-lactam inhibitor of the serine protease prostate-specific antigen . Bioorg. Med. Chem. 2002 , 10 , 1813 – 1818 .
  • Rosenblum , S. B. ; Huynh , T. ; Afonso , A. ; Davis Jr. , H. R. Synthesis of 3-arylpropenyl, 3-arylpropynyl, and 3-arylpropyl 2-azetidinones as cholesterol absorption inhibitors: Application of the palladium-catalyzed arylation of alkenes and alkynes . Tetrahedron 2000 , 56 , 5735 – 5742 .
  • Ojima , I. ; Habus , I. ; Zhao , M. ; Zucco , M. ; Park , Y. H. ; Sun , C. M. ; Brigaud , T. New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method . Tetrahedron 1992 , 48 , 6985 – 7012 .
  • Palomo , C. ; Aizpurua , J. M. ; Ganboa , I. Enantioselective Synthesis of β-Amino Acids ; E. Juaristi (Ed.); Wiley-VCH : New York , 1997 ; pp. 279 – 354 .
  • Boge , T. C. ; Georg , G. I. The Medicinal Chemistry of β-Amino Acids: Paclitaxel as an Illustrative Example ; E. Juaristi (Ed.); Wiley-VCH : New York , 1997; pp. 1–82.
  • Taggi , A. E. ; Hafez , A. M. ; Wack , H. ; Young , B. ; Ferraris , D. ; Lectka , T. The development of the first catalyzed reaction of ketenes and imines: Catalytic, asymmetric synthesis of β-lactams . J. Am. Chem. Soc. 2002 , 124 , 6626 – 6635 .
  • Hegedus , L. S. ; Montgomery , J. ; Narukawa , Y. ; Snustad , D. C. A contribution to the confusion surrounding the reaction of ketenes with imines to produce. β-lactams: A comparison of stereoselectivity dependence on the method of ketene generation: Acid chloride/triethylamine vs photolysis of chromium carbene complexes . J. Am. Chem. Soc. 1991 , 113 , 5784 – 5791 .
  • Meth-Cohn , O. The synthesis of pyridines, quinolines, and other related systems by the Vilsmeier and the reverse Vilsmeier method . Heterocycles 1993 , 35 , 539 – 557 .
  • Rattan , A. Antimicrobials in Laboratory Medicine ; B. I. Churchill (Ed.); Livingstone : New Delhi , 2000 ; pp. 85 – 105 .

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