2015
DOI: 10.3184/174751915x14284938334623
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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-methoxyph… Show more

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Cited by 21 publications
(16 citation statements)
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“…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).…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…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).…”
Section: Resultsmentioning
confidence: 99%
“…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.…”
Section: Synthesis Of Isoxazoline-4-amino Benzylamide (7)mentioning
confidence: 99%
“…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.…”
Section: Introductionmentioning
confidence: 99%
“…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].…”
Section: Introductionmentioning
confidence: 99%