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Relevant academic research and scientific papers

n-alkylamino analogs of Vitamin K3: Electrochemical, DFT and anticancer activity of their oxidized and one electron reduced form

Synthesis, characterization and anticancer activity of reduced form of n-alkylamino analogs of Vitamin K3 (1Na to 8Na) are undertaken. Molecular structure and molecular association of oxidized form of 2-ethylamino-3-methyl-1,4-naphthoquinone (2) and 2-hexylamino-3-methyl-1,4-naphthoquinone (6) were studied by single crystal X-ray analysis. 2 crystallize in monoclinic C2/c and 6 in P21 space group. The reduced form of eight homologated analogs of 2-(n-alkylamino)-3-methyl-1,4-naphthoquinone (1Na to 8Na) were synthesized using sodium metal as reductant at 0 °C in methanol. The formations of naphthosemiquinone radical in 1 to 6 have been confirmed from their EPR spectra. Polycrystalline powder X-band EPR spectra of 1 to 6 shows signals ～2.0020 ± 0.0026 at 133 K. Anticancer activity of 2-(n-alkylamino)-3-methyl-1,4-naphthoquinone (1Na to 8Na) and one electron reduced forms have been evaluated against breast cancer (HeLa) cell line, 1 and 1Na showed promising anticancer activity.

Synthesis and characterization of n-alkylamino derivatives of vitamin K3: Molecular structure of 2-propylamino-3-methyl-1,4-naphthoquinone and antibacterial activities

We would like to introduce eight analogues of n-alkylamino derivatives of vitamin K3 (2-methyl-1,4-naphthoquinone) viz, 2-(n-alkylamino)-3-methyl-1,4-naphthoquinone (where n-alkyl is methyl; LM-1, ethyl; LM-2, propyl; LM-3, butyl; LM-4, pentyl; LM-5, hexyl; LM-6, heptyl; LM-7, octyl; LM-8). All the above analogues have been successfully synthesized from vitamin K3 and characterized using different analytical techniques. Furthermore, in order to understand the mechanistic aspects of formation of LM-1 to LM-8 compounds, we could propose the mechanism. The FT-IR analysis of LM-1 to LM-8 indicate the presence of characteristic band of NH group ～3287-3364 cm-1, the variation was attributed to extensive intramolecular hydrogen bonding interaction. The molecular structure of LM-3 compound has been confirmed by single crystal X-ray diffraction analysis. LM-3 compound crystallises in triclinic space group P1. There were four independent molecules in asymmetric unit cell and their molecular interactions observed via NH.

Synthesis and macrofilaricidal activity of substituted 2-hydroxy/5-hydroxy/ 2-methyl-1,4-naphthoquinones

Preclinical Research Lymphatic filariasis is a disfiguring disease caused by parasitic worms that destroy the human lymphatic system leading to substantial morbidity. The current drug of choice for the treatment of filariasis is diethylcarbamazine and ivermectin with albendazole which are only effective against the microfilaria, leaving the adult worm unaffected, requiring the development of "adulticidal drugs." Thirty amino substituted 2-hydroxy/5-hydroxy/2-methyl-1,4-naphthoquinones were synthesized via the reaction of 2-hydroxy/5-hydroxy/2-methyl-1,4-naphthoquinones with different primary and secondary amines. Compounds 1-30 were evaluated for in vitro antifilarial activity against the adult bovine filarial worm Setaria digitata as assessed by worm motility and MTT (3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazolium bromide) reduction assays. The mutagenecity, tumerogenecity, irritantancy, reproductive toxicity, drug score, druglike, and cLogP properties were calculated using OSIRIS property predictor. Ten compounds showed macrofilaricidal activity with ED50 values ranging between 0.086 and 7.6 μM. Taking into account the biological effects and the promising drug-like profiles of these compounds, these represent valid leads for the development of antifilarial agents against adult filarial worm.

Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity

CDC25 dual-specificity phosphatases are essential key regulators of eukaryotic cell cycle progression and the CDC25A and B isoforms are over-expressed in different tumors and related cancer cell lines. CDC25s are now considered to be interesting targets in the search for novel anticancer agents. We describe new compounds derived from vitamin K3 that inhibit CDC25B activity with IC50 values in the low micromolar range. These naphthoquinone derivatives also display antiproliferative activity on HeLa cells as expected for CDC25 inhibitors and inhibit cell growth in a clonogenic assay at submicromolar concentrations. They increase inhibitory tyrosine 15 phosphorylation of CDK and induce the cleavage of PARP, a hallmark of apoptosis.

Photo-oxidation of 2-methylamino-3-(1-piperidinylmethyl)-1,4-naphthoquinone

2-Methylamino-3-(1-piperidinylmethyl)-1,4 (7) was prepared via several steps from 2-methyl-1,4-naphthoquinone (vitamin K3 3). The quinone (7) was photochemically oxidized to 2-methylamino-3-(1-piperidinylcarbonyl)-1,3-naphthoquinone (8) and/or 2-alkoxycarbonyl-3-methylamino-1,4-naphthoquinone (9), depending on the solvent used.

One-step synthesis of 1,2,3,4-tetrahydrobenzo[g]quinazoline-5,10-dione derivatives from vitamin K3

The reactions of 2-halogenonaphthoquinones (5, 13, 14 and 15) and 2-methyl-1,4-naphthoquinone (20; vitamin K3) with primary and secondary amines were examined. 1,3-Dialkyl-1,2,3,4-tetrahydrobenzo[g]quinazoline-5,10-diones (9) were obtained in moderate yields by treating 20 with formaldehyde in primary amines. A plausible reaction path-way is also presented.