Novel 2,4,5-trisubstituted oxazole derivatives: Synthesis and antiproliferative activity

Liu, Xinhua; Lv, Peng‐Cheng; Xue, Jia‐Yu; Song, Baoan; Zhu, Hai‐Liang

doi:10.1016/j.ejmech.2009.04.019

Cited by 38 publications

(9 citation statements)

References 24 publications

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“…The combination of two active groups in SYP-Z048 would make this compound behave specially. Isoxazolidine or oxazole derivatives have been synthesized for antitumor, antiamoebic, antimicrobial, herbicidal, and fungicidal activities181920212223; many are effective against human pathogens. Activity against plant pathogens by other oxazolidinones and oxazolidine-diones involves inhibition of RNA polymerase I and cytochrome b2425.…”

Section: Discussionmentioning

confidence: 99%

Activity of the novel fungicide SYP-Z048 against plant pathogens

Chen

Han

Liu

et al. 2014

Sci Rep

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In in vitro tests with 18 plant pathogens, the fungicide 3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl] pyridine (SYP-Z048) was highly effective on inhibiting mycelial growth of various ascomycota and basidiomycota, with EC50 values ranging from 0.008 to 1.140 μg/ml. SYP-Z048 had much weaker activity against growth of oomycota with EC50 values > 100 μg/ml. In a second in vitro test with Monilinia fructicola isolates, SYP-Z048 inhibited mycelial growth (EC50 = 0.013 μg/ml), germ tube elongation (EC50 = 0.007 μg/ml), and sporulation but did not affect spore germination. In a detached pear fruit assay inoculated with M. fructicola isolates, SYP-Z048 showed protective and curative activity. Field tests indicated that SYP-Z048 was an efficacious fungicide for control of brown rot disease in two peach orchards. When applied to a single spot on a tomato leaflet in a compound leaf, SYP-Z048 suppressed the growth of Botrytis cinerea isolates on the rest 4 leaflets, indicating that the fungicide has systemic movement in plant tissues. These results indicate that SYP-Z048 has potential for management of brown rot causing by M. fructicola and other diseases caused by ascomycota and basidiomycota.

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Section: Discussionmentioning

confidence: 99%

Activity of the novel fungicide SYP-Z048 against plant pathogens

Chen

Han

Liu

et al. 2014

Sci Rep

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“…2-Bromo-1-(2,3,4-trimethoxyphenyl)ethanone ( 27 ). One mmol of substrate, 3 mmol IL-A, 1.1 mmol NBS, r.t. = 30 min, 55 °C, preparative chromatography SiO 2 , CH 2 Cl 2 , white solid [ 65 ] (44%), mp: 39.8–42.0 °C; 1 H-NMR (CDCl 3 ): δ 7.61 (d, J = 8.9 Hz, 1H), 6.74 (d, J = 8.9 Hz, 1H), 4.57 (s, 2H), 4.05 (s, 3H), 3.93 (s, 3H), 3.87 (s, 3H); IR (NaCl): 2941, 2843, 1680, 1589, 1493, 1464, 1410, 1294, 1213, 1099, 999, 809, 668 cm −1 ; MS (ESI): 289.0 (M+H) + , 291.0 (M+2+H) + .…”

Section: Methodsmentioning

confidence: 99%

Brønsted Acidic Ionic Liquid Accelerated Halogenation of Organic Compounds with N-Halosuccinimides (NXS)

Lü

You

et al. 2012

Molecules

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The Brønsted-acidic ionic liquid 1-methyl-3-(4-sulfobutyl)imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into α-halo and α,α-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of α-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.

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“…Liu et al carried out the preparation of various trisubstituted oxazole derivatives and checked their antitumour potential against two cancer cells, PC-3 (human prostate cancer) and A431(human epidermoid carcinoma)using 5-flourouracil as reference. Among the investigated compounds, 60 , 61 and 62 were the most effective (Table 27) [38].…”

Section: Biological Activities Of Oxazolementioning

confidence: 99%

A comprehensive review on biological activities of oxazole derivatives

2019

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The utility of oxazole as intermediates for the synthesis of new chemical entities in medicinal chemistry have been increased in the past few years. Oxazole is an important heterocyclic nucleus having a wide spectrum of biological activities which drew the attention of researchers round the globe to synthesize various oxazole derivatives and screen them for their various biological activities. The present review article aims to review the work reported on therapeutic potentials of oxazole scaffolds which are valuable for medical applications during new millennium.

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Novel 2,4,5-trisubstituted oxazole derivatives: Synthesis and antiproliferative activity

Cited by 38 publications

References 24 publications

Activity of the novel fungicide SYP-Z048 against plant pathogens

Activity of the novel fungicide SYP-Z048 against plant pathogens

Brønsted Acidic Ionic Liquid Accelerated Halogenation of Organic Compounds with N-Halosuccinimides (NXS)

A comprehensive review on biological activities of oxazole derivatives

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