Synthesis of Sulfanilamido-Naphthoquinones as Potential Antituberculous Agents

Osman, S. A. A.; Abdalla, A. A.; Alaib, M.O.

doi:10.1002/jps.2600720116

Cited by 19 publications

(12 citation statements)

References 4 publications

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“…Naphthoquinones are widely distributed in plants, fungi and some animals 1 and many are found to exhibit an interesting range of pharmacological properties including antibacterial, [2] and [3] antiviral, 4 trypanocidal, 5 anticancer, 6 antimalarial, [7] and [8] and antifungal 9 activity. Other quinone-related scaffolds such as 2-H-pyran-3(6H)-one derivatives 10 natalensis 12 and that of diospyrin 22, isolated from this plant, was observed against drugresistant strains of M. tuberculosis.…”

Section: Introductionmentioning

confidence: 99%

Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase

Mahapatra

Mativandlela

Binneman

et al. 2007

Bioorganic & Medicinal Chemistry

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The naphthoquinone 7-methyljuglone (5-hydroxy-7-methyl-1,4-naphthoquinone) has previously been isolated and identified as an active component of root extracts of Euclea natalensis which displays antitubercular activity. Herein, a series of synthetic and plantderived naphthoquinone derivates of the 7-methyljuglone scaffold have been prepared and evaluated for antibacterial activity against Mycobacterium tuberculosis. Several of these compounds have been shown to operate as subversive substrates with mycothiol disulfide reductase. The absence of a direct correlation between antitubercular activity and subversive substrate efficiency with mycothiol disulfide reductase, might be a consequence of their non-specific reactivity with multiple biological targets (e.g. other disulfide reductases). openUP (December 2007) Graphical abstractArticle Outline

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Section: Introductionmentioning

confidence: 99%

Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase

Mahapatra

Mativandlela

Binneman

et al. 2007

Bioorganic & Medicinal Chemistry

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“…(1). Though this conversion has already been effected in glacial acetic acid under reflux [12], it is now found that the reaction takes place smoothly in water medium without the aid of the acid. It is found that the yield in this method is only marginal (41 %) (method B) [13], but when the reaction is conducted in a mixture of ethanol and acetic acid, by conventional method in acetone and yield between 98 and 99 %.…”

Section: In Vitro Antibacterial Activitymentioning

confidence: 91%

“…Method A [12] A solution of 1,4-naphthoquinone (1.581 g, 10 mmol) in 95 % of ethyl alcohol (40 mL) was gradually added over a period of 30 min to a solution of 4-aminophenyl sulfone (2.048 g, 10 mmol) in glacial acetic acid (10-30 mL) and stirred for 30 min. Then, the mixture was refluxed for 1 h. The reaction mixture was cooled and left overnight at room temperature.…”

Section: General Procedures For Synthesis Of 2-[4-(4-amino-benzene Sumentioning

confidence: 99%

“…This the first report on the synthesis of N-{4-[4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl amino)-benzenesulfonyl]-phenyl}-aryl benzamide derivatives (2-7) and 2-(4-aminobenzosulfonyl)-5H-benzo[b]carbazole-6,11-dione derivatives (1a-7a) to the best of our knowledge. Only few reports are available in literature wherein compounds with carbazoloquinone nuclei on naphthoquinone and N-dansyl carbazoloquinone have been found to exhibit antituberculosis [12] apart from chemical and electrochemical fluorescent activities [14]. However, the molecular docking and antibacterial studies have not been tested on these systems so far (Scheme 1).…”

Section: In Vitro Antibacterial Activitymentioning

confidence: 99%

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Synthesis, molecular docking and antibacterial evaluation of new 1,4-naphthoquinone derivatives contains carbazole-6,11-dione moiety

2014

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A new series of new 1,4-naphthoquinone derivatives containing carbazole-6,11-dione moiety, which has not been reported yet, has been synthesized from 1,4-naphthoquinone and 4-aminophenylsulfone involving a Michael addition, benzoylation, and Pd-catalyzed coupling. This set of compounds has been evaluated for in vitro antibacterial studies against different Gram-positive and Gramnegative bacteria, and most of the synthesized compounds exhibited good antibacterial activity and the minimum inhibitory concentrations (MICs) are compared with the standard drugs used. Compound 7 exhibited good antibacterial activity among all the molecules studied with the best MIC of 2.1 μg/ mL against Bacillus subtilis. To understand the molecular interactions with targeted proteins, the molecular docking of all the synthesized compounds were carried out; between 14 molecules docked, compound 7 was the one with the best glide and E model score of −7.73 and −95.37, respectively. In all docked molecules, compound 5 exhibited least glide and E model score of −4.55 and −101.56, respectively.

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“…There were several drugs discovered for the treatment of TB since 1940 but due to drug resistance cases there is a continuing need to find additional lead compounds and biological targets for novel antitubercular chemotherapies (Gupta et al, 2007). As napthoquinolones were widely distributed in plants, fungi and some animals and many are found to exhibit various pharmacological actions like antibacterial (Osman and Abdalla, 1983;Roshdi et al, 1976), antimalarial (Yardley et al, 1996;Bullock et al, 1970), antiviral (Brinfworth and Fairlie, 1995), trypanocidal (Chemin et al, 2001), anticancer (Hazar et al, 1984), and antifungal (Perry and Blunt, 1991) activity. From the investigation, it was found that the extract of Euclea natalensis (Lall and Meyer, 1999) and diospyrin (a plant isolated product) has significant activity against drug resistant Mycobacterium tuberculosis (Lall and Meyer, 2001).…”

Section: Introductionmentioning

confidence: 99%

QSAR studies of 7-methyljuglone derivatives as antitubercular agents

2011

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The emergence of multidrug resistance strains of Mycobacterium tuberculosis and the continuing pandemic of tuberculosis (TB) leads to the urgent development of the new potent antitubercular agents. Hence, an effort to develop new and more effective agents to treat TB emphasis was focused on quantification of structureactivity relationship of 7-methyljuglone derivatives. A set of twenty-five 7-methyljuglone derivatives with antitubercular activity were subjected to two-dimensional quantitative structure activity relationship study using various combination of thermodynamic, electronic, and spatial descriptors by the software Vlife Molecular Drug Design suite 3.0. After performing QSAR study, it was found that the model developed by multiple linear regression method (Model I) was more statistically significant in compare to the model developed by principle component regression method (Model II), as Model I having correlation coefficient (r) = 0.9591, coefficient of determination (r 2 ) = 0.8823, Fischer test (F) = 39.7105, q 2 = 0.7871, r 2 SE = 0.2112, q 2 SE = 0.2598, pred_r 2 = 0.4916, pred_r 2 SE = 0.7483 relating to descriptors XA-hydrophobic area and dipole moment which were having significant correlation with biological activity. The predictive power of this model was discerned by taking test series which gave significant statistical results. Thus, this validated model brings important structural insight to aid in the design of novel antitubercular agents.

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Synthesis of Sulfanilamido-Naphthoquinones as Potential Antituberculous Agents

Cited by 19 publications

References 4 publications

Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase

Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase

Synthesis, molecular docking and antibacterial evaluation of new 1,4-naphthoquinone derivatives contains carbazole-6,11-dione moiety

QSAR studies of 7-methyljuglone derivatives as antitubercular agents

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