Design, Synthesis and Antifungal Activity of Novel Paeonol Derivatives Linked with 1,2,3-Triazole Moiety by the Click Reaction

Abstract

For obtaining novel bioactive compounds with significant antifungal activities, a series of novel paeonol derivatives linked with a 1,2,3-triazole moiety have been designed and synthesised by a click reaction under mild conditions using Cu(OAc) 2 ·H 2 O/sodium ascorbate as a catalyst. The antifungal activities of all the target compounds were evaluated in vitro against two plant pathogenic fungi, Colletotrichum capsici and Rhizoctonia cerealis. Preliminary results indicated that 1-(4-methoxy-2-{[1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl]-methoxy}phenyl)ethanone showed the best antifungal activities against C. capsici, while 1-(2-{[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]methoxy}-4-methoxyphenyl)ethanone and 1-(4-methoxy-2-{[1-(o-tolyl)-1H-1,2,3-triazol-4yl]methoxy}phenyl)ethanone were found to have better antifungal activities against the tested two fungi. All the synthesised compounds have been determined by IR, HR MS and NMR spectra.Scheme 1 Synthetic routes of the title compounds. Reagents and conditions: (a) NaOH, acetone, reflux, 48h, 23%; (b) Cu(OAc) 2 ·H 2 O(10 mol%), sodium ascorbate (20 mol%), t-BuOH/H 2 O (1:1), ultrasound irradiation, 30 °C. O O

Side chain effect in the modulation of αvβ3/α5β1 integrin activity via clickable isoxazoline-RGD-mimetics: development of molecular delivery systems

“…The synthesis of the simpler compound 26 was accomplished in one step by performing the Huisgen reaction on the acid 8 with ethyl 5-azido-pentanoate. Due to the nature of substrate 8, the conditions of the reaction were modified and Cu(OAc) 2 was used in the presence of sodium ascorbate 27 . The click reaction afforded 26 in 20% yield, as consequence of the difficulties in the purification of the product from the copper salts (Scheme 3, pathway E).…”

“…The crude product was purified by flash chromatography (silica gel, 1/1 EtOAc/cyclohexane) affording the pure product as a colourless oil. General procedure for the Huisgen reaction between methyl ester (7) and azides: (16a), (16b), (19a), (19b), (23), (27). In one-necked round bottom flask, in a mixture of tBuOH:H 2 O = 1:1 (1 ml) TEA (0.15 mmol) and HCl 1 M (0.15 mmol) were added and stirred for 2 min.…”

Design, synthesis, and antitumor activity of novel paeonol derivatives containing the 1,4-benzoxazinone and 1,2,3-triazole moieties

“…Based on all the above considerations and as an extension of our research on the development of novel paeonol derivatives, a new series of paeonol derivatives containing the 1,4-benzoxazinone and 1,2,3-triazole moieties, which could connect more pharmacophores for constructing bioactive and functional molecules, [23][24][25][26][27][28] were synthesized and exhibited preferable inhibitory activity toward human nonsmall cell lung cancer NCI-H1299 cells and human cervical carcinoma HeLa cells.…”

Synthesis and the Biological Activity of Phosphonylated 1,2,3-Triazolenaphthalimide Conjugates

“…Pharmacologically important natural as well as synthetic compounds having various heterocyclic systems including powerful pharmacophores such as triazoles and naphthalimides are of special interest. Numerous compounds of the 1,2,3-triazole family have shown a broad spectrum of biological activities, including antibacterial [1,2], antifungal [3,4,5,6], anticancer [7,8,9,10,11], antiviral [12,13,14,15,16] and antiallergic effects [17]. Furthermore, substituted 1,2,3-triazoles have also been used as agrochemicals, dyes, photostabilisers and corrosion inhibitors [18,19,20].…”