Molecular structures and biological evaluation of 2-chloro-3-(n-alkylamino)-1,4-napthoquinone derivatives as potent antifungal agents

Pawar, Omkar; Patekar, Ashwini; Khan, Ayesha; Kathawate, Laxmi; Haram, Santosh K.; Markad, Ganesh B.; Puranik, Vedavati G.; Salunke‐Gawali, Sunita

doi:10.1016/j.molstruc.2013.11.029

Cited by 37 publications

(18 citation statements)

References 41 publications

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“…Some compounds show strong activity against fungi such as Candida sp. and filamentous fungi (Pawar et al, 2014). These activities depend on the position(s) of the substituents in the naphthoquinone ring (Figs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antibacterial and antifungal activities of naphthoquinone derivatives: a structure–activity relationship study

et al. 2016

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The synthesis of 1,4-naphthoquinone derivatives is of great interest since these compounds exhibit strong activity as antimalarial, antibacterial, antifungal and anticancer agents. A series of 50 naphthoquinone derivatives was synthesized and evaluated for antibacterial and antifungal activity against Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Candida krusei, Candida parapsilosis and Cryptococcus neoformans using the broth microdilution method. The Candida species were the most susceptible microorganisms. Halogen derivatives of 1,4-naphthoquinone presented strong activity, e.g., 2-bromo-5-hydroxy-1,4-naphthoquinone, which exhibited inhibition at an MIC of 16 lg/ mL in S. aureus, and 2-chloro-5,8-dihydroxy-1,4-naphthoquinone, with an MIC of 2 lg/mL in C. krusei. These compounds showed higher activity against fungi, but the antibacterial activities were very low. The study of structure-activity relationships is very important in the search for new antimicrobial drugs due to the limited therapeutic arsenal.

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Section: Introductionmentioning

confidence: 99%

Synthesis, antibacterial and antifungal activities of naphthoquinone derivatives: a structure–activity relationship study

et al. 2016

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“…The carbonyl distance C(2)-O(1) was observed as $1.23Å in M-1B and M-2B,10,[42][43][44][45] while it was longer in M-4B (1.246Å). All the crystallized compounds showed planar polycycles.…”

mentioning

confidence: 87%

“…The n C]O frequency in all compounds was assigned at 1629 AE 1 cm À1 , while n C]N stretching frequency [42][43][44][45] was assigned at 1585 AE 10 cm À1 in the FT-IR spectra except in M-1B it was observed at 1574 cm À1 ( Fig. S22 and Table S1 in ESI †).…”

Section: Introductionmentioning

confidence: 97%

Benzo[α]phenoxazines and benzo[α]phenothiazine from vitamin K3: synthesis, molecular structures, DFT studies and cytotoxic activity

et al. 2015

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Synthesis and characterization of fluorescent benzo[a]phenoxazines viz., M-1B (10-chloro-6-methyl-7a,11a-dihydro-5H-benzo[a]phenoxazin-5-one), M-2B 6,10-dimethyl-7a,11a-dihydro-5H-benzo[a]phenoxazin-5-one), M-3B (6-methyl-7a,11a-dihydro-5H-benzo[a]phenoxazin-5-one) and benzo[a]phenthiazine, M-4B (6-methyl-5H-benzo[a]phenothiazin-5-one) were carried out. 1 H and 13 C chemical shifts were assigned from the 2DgHSQCAD NMR experiments. Compound M-1B crystallizes in the orthorhombic space group P2 1 2 1 2 1 , while M-2B and M-4B crystallize in the monoclinic space group P2 1 /c. The crystal network of M-1B showed slipped p-p stacking and Cl/Cl interactions, while M-2B facilitated ladder like p-p stacked polymeric chains. The C/S contacts were observed in the crystal environment of M-4B. All these structures possess C-H/O interactions. Electronic structure and charge distribution in terms of molecular electrostatic potential and frontier orbital analyses based on the MO6-2X based density functional theory further showed that monomer and dimer structures are in keeping with the single crystal X-ray data and provide insights for the growth of the crystal network. Antiproliferative activity of M-1B-M-4B was determined from the MTT assay against a human breast adenocarcinoma cell line (MCF-7), human carcinoma cell line (HeLa) and normal skin cell line. All these compounds showed significant cytotoxic activity against MCF-7 and HeLa by inducing apoptosis and thus can be viewed as potential candidates for antitumor therapy. Compounds M-2B and M-4B were further found to be topoisomerase II inhibitors.

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“…Naphthoquinones readily act as reducing agents leading to the formation of radicals and reactive oxygen species (ROS) [10]. In the past, several quinones and naphthoquinones were biologically tested and revealed cytostatic properties [6,7,[11][12][13]. Half-sandwich organometallic complexes containing 2-hydroxy- [1,4]-naphthoquinones as ligand scaffold have already been reported in literature with promising results [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations

Mészáros

Geisler

Poljarević

et al. 2020

Journal of Organometallic Chemistry

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Half-sandwich organometallic complexes featuring Ru(II), Os(II) and Rh(III) metal centers and naturally occurring bidentate 2-hydroxy-[1,4]-naphthoquinone ligands (lawsone and phthiocol) have been synthesized and characterized in both solid state and solution phase by analytical, spectroscopic, electrochemical and single crystal X-ray diffraction techniques. Comparative studies revealed the influence of the respective metal center (Ru, Os, Rh), leaving group (Cl, Br, I) and arene (p-cymene, toluene, pentamethylcyclopentadienyl), as well as the naphthoquinone ligand on the structural properties and solution speciation. Additionally, cytotoxicity was tested in SW480, CH1/PA-1 and A549 human cancer cell lines showing a broad range of IC 50 values.

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Molecular structures and biological evaluation of 2-chloro-3-(n-alkylamino)-1,4-napthoquinone derivatives as potent antifungal agents

Cited by 37 publications

References 41 publications

Synthesis, antibacterial and antifungal activities of naphthoquinone derivatives: a structure–activity relationship study

Synthesis, antibacterial and antifungal activities of naphthoquinone derivatives: a structure–activity relationship study

Benzo[α]phenoxazines and benzo[α]phenothiazine from vitamin K3: synthesis, molecular structures, DFT studies and cytotoxic activity

Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations

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