Aminonaphthoquinones in heterocyclization

Aly, Ashraf A.; Ishak, Esam A.; Alsharari, Musaed A.; Al‐Muaikel, Nayef S.; Bedair, Tarek M.

doi:10.1002/jhet.639

Cited by 16 publications

(6 citation statements)

References 62 publications

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“…The natural naphthoquinone products alkannin and shikonin and their derivatives are active against Gram-positive bacteria such as Staphylococcus aureus , Enterococcus faecium and Bacillus subtilis . 2,3-Diamino-1,4-naphthoquinone itself was found to act as an antibacterial agent against Staphylococcus aureus , with IC 50 values ranging from 30 to 125 µg/mL [ 16 ]. The prevalence of strains of Staphylococcus aureus resistant to conventional antibiotics has increased to high levels in some hospitals.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

et al. 2012

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New 3-substituted 1-(3-hydroxyphenyl)-5-oxopyrrolidine derivatives containing hydrazone, azole, diazole, oxadiazole fragments, as well as 2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinone derivatives were synthesized. The structure of all compounds has been confirmed by NMR, IR, mass spectra, and elemental analysis data. Methyl 1-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)oxy]phenyl}-5-oxo-3-pyrrolidinecarboxylate demonstrated potential antibacterial and antifungal activities as determined by diffusion and serial dilution methods, while N'-[(4-bromophenyl)methylidene]-1-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)oxy]phenyl}-5-oxo-3-pyrrolidinecarbohydrazide and 2-{3-[4-(1,2,3-oxadiazol-5-yl)-2-oxo-1-pyrrolidinyl]phenoxy}-3-{3-[4-(1,3,4-oxadiazol-2-yl)-2-oxo-1-pyrrolidinyl]phenoxy}naphthoquinone showed antifungal activity against Candida tenuis and Aspergillus niger at low concentrations, as determined by the serial dilution method. The substitution of the methoxy fragment by N-containing substituents in monophenoxy substituted naphthoquinones was found to decrease their activity against Mycobacterium luteum. Besides, introduction of the second phenoxy substituted fragment increased the antifungal activity against Candida tenuis and Aspergillus niger at lower concentrations.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

et al. 2012

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“…In 2014, Tandon and co-workers [79] reported an efficient and concise one-pot regio-and chemo-selective synthesis of benzo[a]phenazine and derivatives (11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24). As shown in Scheme 3, this method was employed for 2, 3-dichloro-1, 4-naphoquinone to nucleophile with ophenylenediamine and benzamidine under the condition of H 2 O in the presence of alkali and micelles (SDS) as catalysts, achieving the expected products in excellent yields.…”

Section: Benzo[a]phenazine and Derivativesmentioning

confidence: 99%

“…It has been widely explored in the fields of medicine, pesticides, dyes, and conductive materials [5,[8][9][10][11][12][13][14]. Since then, a plenteous of phenazine derivatives have been synthesized and identified due to their attractive performance [15][16][17][18][19]. According to the documents [20][21][22][23][24][25][26], it was firstly reported in the nineteenth century.…”

Section: Introductionmentioning

confidence: 99%

Synthetic strategies of phenazine derivatives: A review

Che

et al. 2022

Journal of Heterocyclic Chem

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Since the growing importance of phenazine derivatives, the efficient synthetic strategies for the preparation of phenazine derivatives have attracted great attention from organic methodology. Herein, we comprehensively review and summarize a series of sustainable and facile synthetic strategies of phenazine derivatives. Moreover, we further discuss the approach of preparation and the superiority of each strategy.

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“…The literature studies listed amino naphthoquinones as one of the prospective lead skeletons for synthesis of several antifungal and antimalarial drugs. Chloroquine, a popular antimalarial drug that had been used for many years, is less efficient against malaria than 2‐amino‐3‐chloro‐1,4‐naphthoquinone 17–19 . Additionally, they have discovered well‐known industrial uses for color chemistry, hair pigments, and photo stabilizers 20 .…”

Section: Introductionmentioning

confidence: 99%

Design, characterization, and different applications of naphthoquinone‐based Schiff base and its M(II/III) complexes with molecular modeling studies

Saleh,

Alminderej,

El‐Sayed

et al. 2024

Applied Organom Chemis

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Due to the significant pharmacophoric role of 1,4‐naphthoquinone moiety, which is found in numerous biologically active natural products and well‐known chemotherapeutic drugs, including doxorubicin, shikonin, and alkannin, a newly prepared ligand ((E)‐1‐((2‐mercaptophenyl)imino)naphthalen‐2(1H)‐one) can be obtained from the condensation of 2‐aminothiophenol with diketone (1,2‐naphthoquinone) to form Schiff base (HL), which has been characterized using elemental analyses, FT‐IR, 1H‐NMR, and mass spectra. The inner ((La(III), Er(III), and Yb(III)) and outer ((Fe(III), Co(II), and Zn(II)) transitionmetal complexes have been prepared in 1:2 ratio and identified by several spectroscopic instruments. Different characterization tools have been used as elemental analyses, 1H‐NMR, molar conductivity, 13C‐NMR, FT‐IR, thermal decomposition (TG and DTG), UV‐vis, X‐ray diffraction, mass spectrometry, solid reflectance, and magnetic moment. All of them are conjugated to confirm the proposed structures of the metal complexes and are complementary. Also, molecular docking studies for the ligand and its Zn(II) and Yb(III) complexes (using MOE program) have been performed to support the experimental biological activity. Molecular docking studies recommended that (Yb(HL)2)Cl3·6H2O complex is more potent against Aspergillus niger fungus when docked with 1Y43 (aspergilloglutamic peptidase enzyme from A. niger) receptor, while Zn(II) complex recorded the strongest binding energy among the docked compounds against 2W3Z(the crystal structure of a Streptococcus mutans CE4 esterase) and 7AB4 (the crystal structure of the Escherichia coli toxin‐antitoxin system HipBST [HipT S59A]) proteins receptors, respectively. Experimental applications of the free ligand and its metal chelates as antimicrobial and antioxidant activities have been carried out. The former occurred against two fungal species (Aspergillus niger [ATCC:16404] and Candida albicans [ATCC:10231]), two G‐positive bacterial species (S. mutans [ATCC:25175] and Staphylococcus aureus [ATCC:13565]) and two G‐negative bacterial species (Klebsiella pneumonia [ATCC:10031] and E. coli [ATCC:10536]). The DPPH scavenging method has been used to measure the antioxidant activity of the tested compounds.

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Aminonaphthoquinones in heterocyclization

Cited by 16 publications

References 62 publications

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

Synthetic strategies of phenazine derivatives: A review

Design, characterization, and different applications of naphthoquinone‐based Schiff base and its M(II/III) complexes with molecular modeling studies

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