Literature DB >> 24900574

Synthesis and antiplasmodial and antimycobacterial evaluation of new nitroimidazole and nitroimidazooxazine derivatives.

Matshawandile Tukulula1, Rajni-Kant Sharma1, Maïa Meurillon1, Aman Mahajan1, Krupa Naran2, Digby Warner2, Jianxing Huang3, Belew Mekonnen3, Kelly Chibale4.   

Abstract

The synthesis and antiplasmodial and antimycobacterial evaluation of two new series of nitroimidazole and nitroimidazooxazine derivatives is described. The majority of these compounds, especially hybrids 9d, 9f, and 14b, exhibited potent activity against the chloroquine-resistant K1 strain of Plasmodium falciparum. Furthermore, a notable number from the tetrazole series were significantly more active against M. tuberculosis than kanamycin, a standard TB drug.

Entities:  

Keywords:  Nitroimidazoles; antimycobacterial activity; antiplasmodial; nitroimidazooxazines

Year:  2012        PMID： 24900574      PMCID： PMC4027538          DOI： 10.1021/ml300362a

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  20 in total

1.  Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).

Authors:  Adrian Blaser; Brian D Palmer; Hamish S Sutherland; Iveta Kmentova; Scott G Franzblau; Baojie Wan; Yuehong Wang; Zhenkun Ma; Andrew M Thompson; William A Denny
Journal:  J Med Chem       Date:  2011-12-29       Impact factor: 7.446

2.  Multidrug-resistant and extensively drug-resistant tuberculosis: a threat to global control of tuberculosis.

Authors:  Neel R Gandhi; Paul Nunn; Keertan Dheda; H Simon Schaaf; Matteo Zignol; Dick van Soolingen; Paul Jensen; Jaime Bayona
Journal:  Lancet       Date:  2010-05-22       Impact factor: 79.321

3.  The design, synthesis, in silico ADME profiling, antiplasmodial and antimycobacterial evaluation of new arylamino quinoline derivatives.

Authors:  Matshawandile Tukulula; Susan Little; Jiri Gut; Philip J Rosenthal; Baojie Wan; Scott G Franzblau; Kelly Chibale
Journal:  Eur J Med Chem       Date:  2012-09-07       Impact factor: 6.514

4.  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

5.  Metronidazole prevents reactivation of latent Mycobacterium tuberculosis infection in macaques.

Authors:  Philana Ling Lin; Veronique Dartois; Paul J Johnston; Christopher Janssen; Laura Via; Michael B Goodwin; Edwin Klein; Clifton E Barry; Joanne L Flynn
Journal:  Proc Natl Acad Sci U S A       Date:  2012-07-23       Impact factor: 11.205

6.  Synthesis and structure-activity relationships of varied ether linker analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine (PA-824).

Authors:  Andrew M Thompson; Hamish S Sutherland; Brian D Palmer; Iveta Kmentova; Adrian Blaser; Scott G Franzblau; Baojie Wan; Yuehong Wang; Zhenkun Ma; William A Denny
Journal:  J Med Chem       Date:  2011-09-01       Impact factor: 7.446

Review 7.  The state of the art in anti-malarial drug discovery and development.

Authors:  Jeremy N Burrows; Kelly Chibale; Timothy N C Wells
Journal:  Curr Top Med Chem       Date:  2011       Impact factor: 3.295

8.  Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase.

Authors:  Romano Silvestri; Marino Artico; Gabriella De Martino; Rino Ragno; Silvio Massa; Roberta Loddo; Chiara Murgioni; Anna Giulia Loi; Paolo La Colla; Alessandra Pani
Journal:  J Med Chem       Date:  2002-04-11       Impact factor: 7.446

9.  Synthesis and structure-activity studies of biphenyl analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).

Authors:  Brian D Palmer; Andrew M Thompson; Hamish S Sutherland; Adrian Blaser; Iveta Kmentova; Scott G Franzblau; Baojie Wan; Yuehong Wang; Zhenkun Ma; William A Denny
Journal:  J Med Chem       Date:  2010-01-14       Impact factor: 7.446

Review 10.  Structure, function, and biogenesis of the cell wall of Mycobacterium tuberculosis.

Authors:  P J Brennan
Journal:  Tuberculosis (Edinb)       Date:  2003       Impact factor: 3.131
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  7 in total

1.  Synthesis and in vitro and in vivo pharmacological evaluation of new 4-aminoquinoline-based compounds.

Authors:  Matshawandile Tukulula; Mathew Njoroge; Efrem T Abay; Grace C Mugumbate; Lubbe Wiesner; Dale Taylor; Liezl Gibhard; Jennifer Norman; Kenneth J Swart; Jiri Gut; Philip J Rosenthal; Samuel Barteau; Judith Streckfuss; Jacques Kameni-Tcheudji; Kelly Chibale
Journal:  ACS Med Chem Lett       Date:  2013-10-01       Impact factor: 4.345

2.  Discovery of autophagy inhibitors with antiproliferative activity in lung and pancreatic cancer cells.

Authors:  Lars Ulrik Nordstrøm; Juan Sironi; Evelyn Aranda; Jorge Maisonet; Roman Perez-Soler; Peng Wu; Edward L Schwartz
Journal:  ACS Med Chem Lett       Date:  2015-01-08       Impact factor: 4.345

3.  Synthesis and in silico ADME/Tox profiling studies of heterocyclic hybrids based on chloroquine scaffolds with potential antimalarial activity.

Authors:  Hegira Ramírez; Esteban Fernandez-Moreira; Juan R Rodrigues; Michael R Mijares; Jorge E Ángel; Jaime E Charris
Journal:  Parasitol Res       Date:  2021-11-15       Impact factor: 2.289

4.  New Quinoline-Urea-Benzothiazole Hybrids as Promising Antitubercular Agents: Synthesis, In Vitro Antitubercular Activity, Cytotoxicity Studies, and In Silico ADME Profiling.

Authors:  Rashmika Moodley; Chakes Mashaba; Goitsemodimo H Rakodi; Nomagugu B Ncube; Mabuatsela V Maphoru; Mohammed O Balogun; Audrey Jordan; Digby F Warner; Rene Khan; Matshawandile Tukulula
Journal:  Pharmaceuticals (Basel)       Date:  2022-05-05

Review 5.  Tetrazoles via Multicomponent Reactions.

Authors:  Constantinos G Neochoritis; Ting Zhao; Alexander Dömling
Journal:  Chem Rev       Date:  2019-02-01       Impact factor: 60.622

Review 6.  Modifications of quinolones and fluoroquinolones: hybrid compounds and dual-action molecules.

Authors:  Joanna Fedorowicz; Jarosław Sączewski
Journal:  Monatsh Chem       Date:  2018-06-07       Impact factor: 1.451

7.  Antiplasmodial Activity of Nitroaromatic Compounds: Correlation with Their Reduction Potential and Inhibitory Action on Plasmodium falciparum Glutathione Reductase.

Authors:  Audronė Marozienė; Mindaugas Lesanavičius; Elisabeth Davioud-Charvet; Alessandro Aliverti; Philippe Grellier; Jonas Šarlauskas; Narimantas Čėnas
Journal:  Molecules       Date:  2019-12-10       Impact factor: 4.411
  7 in total

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