Reactions of 2,3-dichloro-1,4-naphthoquinone with aminophenols: evidence for hydroxy benzophenoxazine intermediate and antibacterial activity

Choudhari, Dinkar; Lande, Dipali N.; Chakravarty, Debamitra; Gejji, Shridhar P.; Das, Parijat; Pardesi, Karishma; Satpute, Surekha K.; Salunke‐Gawali, Sunita

doi:10.1016/j.molstruc.2018.08.066

Cited by 10 publications

(19 citation statements)

References 36 publications

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“…Molecular structures of most of the derivatives revealed from single-crystal X-ray diffraction studies. The majority of these compounds possess biological activity, for example, antibacterial [ 30 ], antifungal [ 28 ], and antiproliferative activity [ 31 , 32 , 34 , 44 ].…”

Section: Resultsmentioning

confidence: 99%

1H and 13C NMR chemical shifts of 2-n-alkylamino-naphthalene-1,4-diones

Patil

Jadhav

Salunke‐Gawali

et al. 2021

Heliyon

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1 H as well as 13 C chemical shifts of 32 compounds of C (3) substituted 2-( n -alkylamino)-3R-naphthalene-1,4-dione (where n -alkyl: methyl, to octyl, R = H, Cl, Br, and CH 3 ) are investigated through 1 H, 13 C, DEPT, gDQCOSY, and gHSQCAD NMR experiments and M06-2X/6-311++G (d,p) density functional theory are discussed. Single crystal X-ray structure of Br-3, as well as 18 different derivatives of naphthalene-1,4-diones, are revealed for its inter and intra-molecular hydrogen bonding interactions.

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Section: Resultsmentioning

confidence: 99%

1H and 13C NMR chemical shifts of 2-n-alkylamino-naphthalene-1,4-diones

Patil

Jadhav

Salunke‐Gawali

et al. 2021

Heliyon

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“…The synthesis of the derivatives in the second group (8)(9)(10)(11)(12)(13)(14)(15)(16) with the pyridinylamino or dibenzylamino groups on their side chains is shown in Chart 2. Specifically, 4-methyl-2-aminopyridine and dibenzylamine were used as aromatic amines in the Mannich reaction.…”

Section: Chemical and Pharmaceutical Bulletin Advance Publicationmentioning

confidence: 99%

“…In this regard, none of these components approached the capability of Chemical and Pharmaceutical Bulletin Advance Publication the reference drugs in terms of their inhibitory activity against Plasmodium falciparum. However, the results revealed that ten naphthoquinones (1)(2)(3)(4)(5)(6)(7)(8)11,13) significantly displayed good antimalarial activity with IC 50 values in the range of 0.77-4.05 g/mL while the other members of the series (9,10,12,(14)(15)(16) were found to be inactive against the parasite. Among the tested compounds, the best antimalarial efficacy was observed in the n-butyl substituted aminomethyl lawsone derivative (1) with an IC 50 value of 0.77 g/mL.…”

Section: Chemical and Pharmaceutical Bulletin Advance Publicationmentioning

confidence: 99%

“…The naphthoquinone derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) were subjected to in-vitro anti-malaria evaluation against Plasmodium falciparum. Bioassay was performed in the Laboratory of the National Center for Generic Engineering and Biotechnology (BIOTECH), Thailand.…”

Section: Biological Activitymentioning

confidence: 99%

“…[11][12][13][14] Within these studies, the 1,4-naphthoquinone analogues have been found to possess not only antimalarial activity but also a diverse range of biological activities, such as antioxidant, antibacterial, antitumor, antituberculosis activities. [14][15][16][17][18] Aminonaphthoquinone belongs to the quinone family which possesses an interesting scaffold conveying potential for a range of pharmacological applications. 19,20) Previously published literature reported that incorporation of amino groups or N-containing fragments into the 1,4-naphthoquinone skeleton resulted in increased levels of antiplasmodial activity, [20][21][22] as well as many other significantly beneficial biological properties such as antitumor, antifungal, antibacterial, antiplatelet, anti-allergic and anti-inflammatory activities.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Evaluation of 2-Hydroxy-1,4-naphthoquinone Derivatives as Potent Antimalarial Agents

Paengsri

Promsawan

Baramee

2021

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of 3-substituted-2-hydroxy-1,4-naphthoquinone derivatives with a variety of side chains were successfully synthesized by Mannich reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with selected amines and aldehydes. All substances (1-16) were evaluated for in-vitro antimalarial activity against strains of Plasmodium falciparum by microculture radioisotope technique. Bioassay data revealed that ten derivatives (1-8,11 and 13) displayed significantly good activity with values of IC 50 ranging from 0.77 to 4.05 g/mL. The best biological profile (IC 50 = 0.77 g/mL) was observed in compound 1, possessing a n-butyl substituted aminomethyl group. Experimental results support the potential use of our active Mannich components as promising antimalarial agents in the fight against malaria infections and multidrug resistance problems.

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Thiourea Derivatives Based on the Dapsone‐Naphthoquinone Hybrid as Anticancer and Antimicrobial Agents: In Vitro Screening and Molecular Docking Studies

2020

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According to the structure‐activity relationships (SAR), we synthesized a series of novel thiourea derivatives based on the dapsone‐naphthoquinone hybrid by the nucleophilic addition reaction of various primary/secondary amines to 2‐[4‐(4‐isothiocyanato‐benzenesulfonyl)‐phenylamino]‐[1,4]naphthoquinone (4). All thiourea derivatives (5 a‐j) were screened for in vitro anticancer activity against human leukemia cell line (K562). Thiourea derivative containing N‐methyl piperazine (5 h) was identified as the most effective molecule with IC50= 5.8±0.55 μM. Antimicrobial activity of thiourea derivatives (5 a–j) was evaluated in vitro against six strains of bacteria (Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, Escherichia coli, Salmonella enterica and Klebsiella pneumoniae) and a fungus Candida kefyr by the microdilution method. Interestingly, compound 5 h exhibited better antibacterial activity compared with the dapsone as a positive control against S. epidermidis. The molecular docking studies indicated that compound 5 h may act as anticancer agent through the inhibition of Abl kinase and T315I Abl mutant.

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Reactions of 2,3-dichloro-1,4-naphthoquinone with aminophenols: evidence for hydroxy benzophenoxazine intermediate and antibacterial activity

Cited by 10 publications

References 36 publications

1H and 13C NMR chemical shifts of 2-n-alkylamino-naphthalene-1,4-diones

1H and 13C NMR chemical shifts of 2-n-alkylamino-naphthalene-1,4-diones

Synthesis and Evaluation of 2-Hydroxy-1,4-naphthoquinone Derivatives as Potent Antimalarial Agents

Thiourea Derivatives Based on the Dapsone‐Naphthoquinone Hybrid as Anticancer and Antimicrobial Agents: In Vitro Screening and Molecular Docking Studies

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