Discovery of novel phenoxazinone derivatives as DKK1/LRP6 interaction inhibitors: Synthesis, biological evaluation and structure–activity relationships

Thysiadis, Savvas; Mpousis, Spyros; Avramidis, Nicolaos; Katsamakas, Sotirios; Balomenos, Athanasios D.; Remelli, Rosaria; Efthimiopoulos, Spiros; Sarli, Vasiliki

doi:10.1016/j.bmc.2016.01.025

Cited by 6 publications

(2 citation statements)

References 40 publications

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“…After drying, the product was characterized by IR, 1 H NMR, 13 C NMR and MS. IR (KBr) v/cm −1 : 3432, 1628-1600 (these peaks are related to conjugated imine group), 1500, 1445, 1384, 1192, 1146, 1060, 974, 751, 689, 93 594, 463. 1 (19), 257 (18), 252 (16), 233 (23), 218 (17), 203 (16.5), 188 (17), 173 (34), 158 (27), 130 (72), 103 (34), 98 (15), 77 (52), 51 (15). The diagram includes three different lines.…”

Section: Methodsmentioning

confidence: 99%

“…[8][9][10][11][12] The synthesis of the phenoxazine core has been performed via a number of chemical methods. [13][14][15][16][17][18] However, these methods have some disadvantages including toxic organic solvents, long reaction time, expensive reagents, harsh reaction conditions and low production yields. These drawbacks and the notion that the other phenoxazines, like dactinomycin, could also possess antitumor activities, have encouraged us to develop a green and facile procedure for the synthesis of a new type of phenoxazine compound.…”

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confidence: 99%

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Electrochemical Study of 1,5-Diaminonaphthalene in Aqueous Solution: Assessing Electrochemistry as a Green Synthetic Tool for the Synthesis of 4-Imino-4H-dibenzo[a,h]phenoxazin-11-ol

Lang¹,

Nematollahi²,

Massah³

et al. 2017

J. Electrochem. Soc.

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The electrochemical behavior of 1,5-diaminonaphthalene (1,5DAN) was studied by cyclic voltammetry and controlled-potential coulometry methods in aqueous ethanol (water/ethanol, 70/30 v/v). The effect of different parameters such as solution pH (from 2 to 10), potential scan rate and 1,5DAN concentration on its electrochemical behavior was studied. The electrochemical synthesis of 4-imino-4H-dibenzo[a,h]phenoxazin-11-ol (IDP) was achieved in high yield (87%) by electrooxidation in water (bicarbonate buffer, c = 0.2 M, pH = 9.0)/ethanol (70/30, v/v) in a one-pot process. The proposed mechanism involves the Michael addition of 1,5DAN to 1,5-naphthalendione (from the hydrolysis of the electrogenerated naphthalene-1,5-diimine (1,5DANox)) followed by oxidation of the 1,5-diaminonaphthalene moiety, cyclization, aromatization, and a final oxidation. Polymerization of 1,5DAN was not observed. The present work provides a green and environmentally friendly method with high atom economy for the synthesis of IDP in an undivided cell under constant current. In addition, IDP showed antibacterial activity against Gram-positive bacteria Bacillus cereus and Staphylococcus aureus.

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