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Literature DB >> 16722620

Identification of new diamine scaffolds with activity against Mycobacterium tuberculosis.

Elena Bogatcheva¹, Colleen Hanrahan, Boris Nikonenko, Rowena Samala, Ping Chen, Jacqueline Gearhart, Francis Barbosa, Leo Einck, Carol A Nacy, Marina Protopopova.

Abstract

A diverse 5000-compound library was synthesized from commercially available diamines and screened for activity against Mycobacterium tuberculosis in vitro, revealing 143 hits with minimum inhibitory concentration (MIC) equal to or less than 12.5 microM. New prospective scaffolds with antitubercular activity derived from homo-piperazine, phenyl- and benzyl-substituted piperazines, 4-aminomethylpiperidine, 4-aminophenylethylamine, and 4,4'-methylenebiscyclohexylamine were identified. Compound SQ775 derived from homopiperazine and compound SQ786 derived from benzylpiperazine had potent antimicrobial activity against M. tuberculosis in experimental animals in vivo.

Entities: Chemical Species

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Year: 2006 PMID： 16722620 PMCID： PMC4869334 DOI： 10.1021/jm050948+

Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446

18 in total

1. Infectious disease. Drug-resistant TB on the rise.

Authors: E Stokstad
Journal: Science Date: 2000-03-31 Impact factor: 47.728

2. Antituberculosis agents. VI. Activity of a new ciprofloxacin derivative against Mycobacterium avium and some drug-resistant strains of Mycobacterium tuberculosis.

Authors: A Foroumadi; F Soltani; M H Moshafi
Journal: Boll Chim Farm Date: 2002 Sep-Oct

3. Low-dose aerosol infection model for testing drugs for efficacy against Mycobacterium tuberculosis.

Authors: B P Kelly; S K Furney; M T Jessen; I M Orme
Journal: Antimicrob Agents Chemother Date: 1996-12 Impact factor: 5.191

4. Combinatorial lead optimization of [1,2]-diamines based on ethambutol as potential antituberculosis preclinical candidates.

Authors: Richard E Lee; Marina Protopopova; Emma Crooks; Richard A Slayden; Marianne Terrot; Clifton E Barry
Journal: J Comb Chem Date: 2003 Mar-Apr

5. Identification of a new antitubercular drug candidate, SQ109, from a combinatorial library of 1,2-ethylenediamines.

Authors: Marina Protopopova; Colleen Hanrahan; Boris Nikonenko; Rowena Samala; Ping Chen; Jackie Gearhart; Leo Einck; Carol A Nacy
Journal: J Antimicrob Chemother Date: 2005-09-19 Impact factor: 5.790

Review 6. Drug-resistant tuberculosis: review of the worldwide situation and the WHO/IUATLD Global Surveillance Project. International Union Against Tuberculosis and Lung Disease.

Authors: D L Cohn; F Bustreo; M C Raviglione
Journal: Clin Infect Dis Date: 1997-01 Impact factor: 9.079

7. Targeting tuberculosis and malaria through inhibition of Enoyl reductase: compound activity and structural data.

Authors: Mack R Kuo; Hector R Morbidoni; David Alland; Scott F Sneddon; Brian B Gourlie; Mark M Staveski; Marina Leonard; Jill S Gregory; Andrew D Janjigian; Christopher Yee; James M Musser; Barry Kreiswirth; Hiroyuki Iwamoto; Remo Perozzo; William R Jacobs; James C Sacchettini; David A Fidock
Journal: J Biol Chem Date: 2003-02-26 Impact factor: 5.157

8. Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug.

Authors: Lee Jia; Joseph E Tomaszewski; Colleen Hanrahan; Lori Coward; Patricia Noker; Gregory Gorman; Boris Nikonenko; Marina Protopopova
Journal: Br J Pharmacol Date: 2005-01 Impact factor: 8.739

9. Synthesis and evaluation of nitrofuranylamides as novel antituberculosis agents.

Authors: Rajendra P Tangallapally; Raghunandan Yendapally; Robin E Lee; Kirk Hevener; Victoria C Jones; Anne J M Lenaerts; Michael R McNeil; Yuehong Wang; Scott Franzblau; Richard E Lee
Journal: J Med Chem Date: 2004-10-07 Impact factor: 7.446

10. Structure-activity relationships of the quinolone antibacterials against mycobacteria: effect of structural changes at N-1 and C-7.

Authors: T E Renau; J P Sanchez; J W Gage; J A Dever; M A Shapiro; S J Gracheck; J M Domagala
Journal: J Med Chem Date: 1996-02-02 Impact factor: 7.446

38 in total

1. Drug therapy of experimental tuberculosis (TB): improved outcome by combining SQ109, a new diamine antibiotic, with existing TB drugs.

Authors: Boris V Nikonenko; Marina Protopopova; Rowena Samala; Leo Einck; Carol A Nacy
Journal: Antimicrob Agents Chemother Date: 2007-01-22 Impact factor: 5.191

Review 2. Discovery and development of SQ109: a new antitubercular drug with a novel mechanism of action.

Authors: Katherine A Sacksteder; Marina Protopopova; Clifton E Barry; Koen Andries; Carol A Nacy
Journal: Future Microbiol Date: 2012-07 Impact factor: 3.165

3. Substrate and reaction specificity of Mycobacterium tuberculosis cytochrome P450 CYP121: insights from biochemical studies and crystal structures.

Authors: Matthieu Fonvielle; Marie-Hélène Le Du; Olivier Lequin; Alain Lecoq; Mickaël Jacquet; Robert Thai; Steven Dubois; Guillaume Grach; Muriel Gondry; Pascal Belin
Journal: J Biol Chem Date: 2013-04-25 Impact factor: 5.157

Identification of new diamine scaffolds with activity against Mycobacterium tuberculosis.

1. Infectious disease. Drug-resistant TB on the rise.

2. Antituberculosis agents. VI. Activity of a new ciprofloxacin derivative against Mycobacterium avium and some drug-resistant strains of Mycobacterium tuberculosis.

3. Low-dose aerosol infection model for testing drugs for efficacy against Mycobacterium tuberculosis.

4. Combinatorial lead optimization of [1,2]-diamines based on ethambutol as potential antituberculosis preclinical candidates.

5. Identification of a new antitubercular drug candidate, SQ109, from a combinatorial library of 1,2-ethylenediamines.

Review 6. Drug-resistant tuberculosis: review of the worldwide situation and the WHO/IUATLD Global Surveillance Project. International Union Against Tuberculosis and Lung Disease.

7. Targeting tuberculosis and malaria through inhibition of Enoyl reductase: compound activity and structural data.

8. Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug.

9. Synthesis and evaluation of nitrofuranylamides as novel antituberculosis agents.

10. Structure-activity relationships of the quinolone antibacterials against mycobacteria: effect of structural changes at N-1 and C-7.

1. Drug therapy of experimental tuberculosis (TB): improved outcome by combining SQ109, a new diamine antibiotic, with existing TB drugs.

Review 2. Discovery and development of SQ109: a new antitubercular drug with a novel mechanism of action.

3. Substrate and reaction specificity of Mycobacterium tuberculosis cytochrome P450 CYP121: insights from biochemical studies and crystal structures.

4. Identification of SQ609 as a lead compound from a library of dipiperidines.

5. Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines.

6. N-(2-Hydroxy-ethyl)-N-(tricyclo-[3.3.1.1]dec-2-yl)benzamide.

7. Discovery of dipiperidines as new antitubercular agents.

8. 4-[Bis(4-fluoro-phen-yl)meth-yl]piperazin-1-ium bis-(trichloro-acetate) 0.4-hydrate.

9. 1-[Bis(4-fluoro-phen-yl)meth-yl]piperazine.

10. 4-[Bis(4-fluoro-phen-yl)meth-yl]-1-[(2E)-3-phenyl-prop-2-en-1-yl]piperazin-1-ium 3-carb-oxy-propano-ate.