Synthesis and biological evaluation of novel 1,4-naphthoquinone derivatives as antibacterial and antiviral agents

Tandon, Vishnu K.; Yadav, Dharmendra B.; Singh, Ratna; Vaish, M.; Chaturvedi, A. K.; Shukla, Praveen Kumar

doi:10.1016/j.bmcl.2005.04.075

Cited by 81 publications

(32 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The antibacterial activity of all the synthesized compounds was tested against Staphylococcus aureus (ATCC 6571), Staphylococcus epidermidis (ATCC 155), Escherichia coli (ATCC 10418) and Pseudomonas aeruginosa (ATCC 10662) using nutrient agar medium (Hi-Media Laboratories, India) by the method of Tandon et al(2005). The sterilized (autoclaved at 120 °C for 30 min) medium (40~50 °C) was inoculated (1 ml/100 ml of medium) with the suspension (105 CFU/ml) of the microorganism (matched to McFarland barium sulphate standard) and poured into a petridish to a depth of 3~4 mm.…”

Section: Antimicrobial Acivitymentioning

confidence: 99%

Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2′-hydroxy)benzylideneaminonaphthothiazole as potential antimicrobial agents

Azam

Singh

Khokhra

et al. 2007

J. Zhejiang Univ. - Sci. B

View full text Add to dashboard Cite

Abstract:Objective: A series of 2-benzylideneaminonaphthothiazoles were designed and synthesized incorporating the lipophilic naphthalene ring to render them more capable of penetrating various biomembranes. Methods: Schiff bases were synthesized by the reaction of naphtha[1,2-d]thiazol-2-amine with various substituted aromatic aldehydes. 2-(2'-Hydroxy)benzylideneaminonaphthothiazole was converted to its Co(II), Ni(II) and Cu(II) metal complexes upon treatment with metal salts in ethanol. All the compounds were evaluated for their antibacterial activities by paper disc diffusion method with Gram positive Staphylococcus aureus and Staphylococcus epidermidis and Gram negative Escherichia coli and Pseudomonas aeruginosa bacteria. The minimum inhibitory concentrations of all the Schiff bases and metal complexes were determined by agar streak dilution method. Results: All the compounds moderately inhibited the growth of Gram positive and Gram negative bacteria. In the present study among all Schiff bases 2-(2'-hydroxy)benzylideneaminonaphthothiazole showed maximum inhibitory activity and among metal complexes Cu(II) metal complex was found to be most potent. Conclusion: The results obtained validate the hypothesis that Schiff bases having substitution with halogens, hydroxyl group and nitro group at phenyl ring are required for the antibacterial activity while methoxy group at different positions in the aromatic ring has minimal role in the inhibitory activity. The results also indicated that the metal complexes are better antibacterial agents as compared to the Schiff bases.

show abstract

Section: Antimicrobial Acivitymentioning

confidence: 99%

Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2′-hydroxy)benzylideneaminonaphthothiazole as potential antimicrobial agents

Azam

Singh

Khokhra

et al. 2007

J. Zhejiang Univ. - Sci. B

View full text Add to dashboard Cite

show abstract

“…Literature survey shows that sulphur play significant role in enhancement of biological activity (Tandon et al, 2005(Tandon et al, , 2006. Sulphur-containing heterocyclic rings, such as thiazole, isothiazole, thiadiazole, thiazepine, tiophene, or benzothiazole are nuclei of antiviral (Vicini et al, 2003;Venkatachalam et al, 2004;Wang et al, 2006;Mercorelli et al, 2009;Struga et al, 2009), antibacterial (Foroumadi et al, 2005;Bozdag-Dündar et al, 2007;Prasad and Kishore, 2007;Stefańska et al, 2009;Tandon et al, 2009) and antifungal (Stefańska et al, 2009) agents.…”

Section: Introductionmentioning

confidence: 99%

Biological evaluation of novel 1,4-dithiine derivatives as potential antimicrobial agents

et al. 2010

View full text Add to dashboard Cite

The preparation of twelve aminoalkanol derivatives of 2,3-dihydro-5H-[1,4] dithiino[2,3-c]pyrrole- 5,7(6H)-dione was described. Newly obtained compounds, as well as their propyl and butyl analogues, were evaluated in vitro against selected viruses. Selected derivatives were tested for their antibacterial and antifungal activity. Compounds 3h, 3j, 4b and 5a-d showed moderate to significant protections against CVB-2, HSV-1 and YFV viruses. The molecular structures of 4a, 5c and 5g were determined by an X-ray analysis

show abstract

“…1), including antibacterial, antitrypanosome, antiviral, antiparasitic, antiplasmodial, antiinflammatory, antiproliferative and antimalarial. [1][2][3][4][5] As proved by our group 6) and Ahn's team, 7) 6-substituted 5,8-dimethoxy-1,4-naphthoquinone (DMNQ) derivatives display a higher inhibitory efficiency on DNA topoisomerase-I and the cytotoxicity against cancer cells compared with the corresponding 2-substituted derivatives due to less steric hindrance on the naphthalene ring. 8) The main mechanisms of naphthoquinones acting inhibitory activity are ascribed to the generation of reactive oxygen species (ROS) and bioreductive alkylation.…”

mentioning

confidence: 99%

“…After stirring for 1 h, a solution of bromo isopentane (0.68g, 4.5 mmol) dissolved in anhydrous DMF (3 mL) and a catalytic amount of iodine were added to the reaction mixture, which was stirred at 60°C overnight. After cooled to the room temperature, the reaction mixture was quenched with saturated NH 4 Cl solution and then extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na 2 SO 4 .…”

Section: 58-trimethoxy-2-naphthaldehyde (2)mentioning

confidence: 99%

“…After stirring at 50°C for 2 h, a solution of naphthaldehyde (2 or 9, 0.5 g, 2.03 mmol) in anhydrous THF (5.0 mL) was added to the solution of alkylmagnesium bromide prepared above. The solution was stirred at room temperature for 3 h and then quenched with saturated NH 4 Cl solution. The mixture was extracted with dichloromethane and washed with brine and then dried over anhydrous Na 2 SO 4 .…”

Section: 58-trimethoxy-2-naphthaldehyde (2)mentioning

confidence: 99%

See 1 more Smart Citation

Cytotoxicity of Synthesized 1,4-Naphthoquinone Oxime Derivatives on Selected Human Cancer Cell Lines

Zhang

Dong

Cui

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

Synthesis and biological evaluation of novel 1,4-naphthoquinone derivatives as antibacterial and antiviral agents

Cited by 81 publications

References 12 publications

Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2′-hydroxy)benzylideneaminonaphthothiazole as potential antimicrobial agents

Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2′-hydroxy)benzylideneaminonaphthothiazole as potential antimicrobial agents

Biological evaluation of novel 1,4-dithiine derivatives as potential antimicrobial agents

Cytotoxicity of Synthesized 1,4-Naphthoquinone Oxime Derivatives on Selected Human Cancer Cell Lines

Contact Info

Product

Resources

About