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Literature DB >> 21705218

Synthesis and evaluation of 1-cyclopropyl-2-thioalkyl-8-methoxy fluoroquinolones.

Kevin R Marks¹, Muhammad Malik, Arkady Mustaev, Hiroshi Hiasa, Karl Drlica, Robert J Kerns.

Abstract

Novel fluoroquinolone derivatives substituted with a 2-thioalkyl moiety, with and without a concomitant 3-carboxylate group, were synthesized to evaluate the effect of C-2 thioalkyl substituents on gyrase binding and inhibition. The presence of a 2-thioalkyl group universally decreased activity as compared to parent fluoroquinolones. However, with derivatives of moxifloxacin the presence of either a 2-thioalkyl group or a 3-carboxylate moiety increased activity over the 2,3-unsubstituted derivative. Energy minimization of structures provides an explanation for relative activities of fluoroquinolones having a C-2 thio moiety.

Entities: Chemical Disease Gene Species

Mesh：

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Year: 2011 PMID： 21705218 PMCID： PMC3138821 DOI： 10.1016/j.bmcl.2011.05.112

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

33 in total

1. 3-hydroxy-quinazoline-2,4-dione as a useful scaffold to obtain selective Gly/NMDA and AMPA receptor antagonists.

Authors: Vittoria Colotta; Daniela Catarzi; Flavia Varano; Francesca Romana Calabri; Guido Filacchioni; Chiara Costagli; Alessandro Galli
Journal: Bioorg Med Chem Lett Date: 2004-05-03 Impact factor: 2.823

2. Synthesis and antibacterial activity of novel 7-substituted-6-fluoro-1- fluoromethyl-4-oxo-4H-[1,3thiazeto[3,2-a]quinoline-3-carboxylic acid derivatives.

Authors: M Matsuoka; J Segawa; I Amimoto; Y Masui; Y Tomii; M Kitano; M Kise
Journal: Chem Pharm Bull (Tokyo) Date: 1999-12 Impact factor: 1.645

Review 3. The quinolones: decades of development and use.

Authors: A M Emmerson; A M Jones
Journal: J Antimicrob Chemother Date: 2003-05 Impact factor: 5.790

4. Structural basis of quinolone inhibition of type IIA topoisomerases and target-mediated resistance.

Authors: Alexandre Wohlkonig; Pan F Chan; Andrew P Fosberry; Paul Homes; Jianzhong Huang; Michael Kranz; Vaughan R Leydon; Timothy J Miles; Neil D Pearson; Rajika L Perera; Anthony J Shillings; Michael N Gwynn; Benjamin D Bax
Journal: Nat Struct Mol Biol Date: 2010-08-29 Impact factor: 15.369

Review 5. Fluoroquinolones: action and resistance.

Authors: Karl Drlica; Muhammad Malik
Journal: Curr Top Med Chem Date: 2003 Impact factor: 3.295

6. Studies on pyridonecarboxylic acids. 1. Synthesis and antibacterial evaluation of 7-substituted-6-halo-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3- carboxylic acids.

Authors: J Segawa; M Kitano; K Kazuno; M Matsuoka; I Shirahase; M Ozaki; M Matsuda; Y Tomii; M Kise
Journal: J Med Chem Date: 1992-12-11 Impact factor: 7.446

7. Studies on pyridonecarboxylic acids. III. Synthesis and antibacterial activity evaluation of 1,8-disubstituted 6-fluoro-4-oxo-7-piperazinyl-4H-[1,3]thiazeto[3,2- a]quinoline-3-carboxylic acid derivatives.

Authors: J Segawa; K Kazuno; M Matsuoka; I Shirahase; M Ozaki; M Matsuda; Y Tomii; M Kitano; M Kise
Journal: Chem Pharm Bull (Tokyo) Date: 1995-01 Impact factor: 1.645

Synthesis and evaluation of 1-cyclopropyl-2-thioalkyl-8-methoxy fluoroquinolones.

1. 3-hydroxy-quinazoline-2,4-dione as a useful scaffold to obtain selective Gly/NMDA and AMPA receptor antagonists.

2. Synthesis and antibacterial activity of novel 7-substituted-6-fluoro-1- fluoromethyl-4-oxo-4H-[1,3thiazeto[3,2-a]quinoline-3-carboxylic acid derivatives.

Review 3. The quinolones: decades of development and use.

4. Structural basis of quinolone inhibition of type IIA topoisomerases and target-mediated resistance.

Review 5. Fluoroquinolones: action and resistance.

6. Studies on pyridonecarboxylic acids. 1. Synthesis and antibacterial evaluation of 7-substituted-6-halo-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3- carboxylic acids.

7. Studies on pyridonecarboxylic acids. III. Synthesis and antibacterial activity evaluation of 1,8-disubstituted 6-fluoro-4-oxo-7-piperazinyl-4H-[1,3]thiazeto[3,2- a]quinoline-3-carboxylic acid derivatives.

Review 8. Structure-activity and structure-side-effect relationships for the quinolone antibacterials.

9. Ciprofloxacin dimers target gyrase in Streptococcus pneumoniae.

10. Synthesis and antibacterial activity of new tetracyclic quinolone antibacterials.

1. The C7-aminomethylpyrrolidine group rescues the activity of a thio-fluoroquinolone.