Anti-influenza Virus Activities of 2-Alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides

Kai, Hiroyuki; Matsumoto, Hiroshi; Hattori, Naohiko; Takase, Akira; Fujiwara, Tamio; Sugimoto, H.

doi:10.1016/s0960-894x(01)00362-6

Cited by 41 publications

(19 citation statements)

References 11 publications

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“…1 H-NMR (400 MHz) and 13 C NMR (100 MHz) spectra were measured on CDCl 3 and tetramethylsilane is used as internal reference. The mass analysis was performed on HP-5989A LC/MS spectrometer.…”

Section: Generalmentioning

confidence: 99%

“…Among them five-membered heterocycles, isoxazolines are of considerable interest due to their versatile application in pharmaceutical and agrochemical agents. Isoxazoline derivatives have been reported to possess antidiabetic, 1 antiinfluenza virus, 2 antifungal, 3 glycoprotein IIb/IIIa receptor antagonists, 4 antiHIV, 5 spermicidal and antiHIV, 6 analgesic and antiinflammatory, 7 and β-adrenergic receptor antagonist, 8 antitumour, 9 antistress 10 and anticancer properties. 11 Isoxazolines also act as an important building block for the synthesis of biologically active molecules.…”

Section: Introductionmentioning

confidence: 99%

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One-pot synthesis of new series 3,4,5-trisubstituted–dihydroisoxazoline derivatives via 1,3-dipolar cycloaddition of nitrile oxides with chalcones

2013

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Section: Generalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

One-pot synthesis of new series 3,4,5-trisubstituted–dihydroisoxazoline derivatives via 1,3-dipolar cycloaddition of nitrile oxides with chalcones

2013

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“…Measured the absorbance at 570 nm in Tecan plate reader and repeated the entire experiment twice and the ± SD was calculated and reported in Table 2. 25 …”

Section: In-vitro Cytotoxicity Assay Using Calu-6 Cellsmentioning

confidence: 99%

“…Substituted isoxazolines have revealed anti-influenza virus, 25 antifungal, 26 antitubercular, 27 spermicidal and anti-HIV, 28 β-adrenergic receptor antagonist, 29 analgesic and anti-inflammatory 30 properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial and cytotoxicity studies of some novel modified Strobilurin derivatives

Sridhara¹,

Reddy²,

Keshavayya³

et al. 2011

J. Braz. Chem. Soc.

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Uma série de novas 3-isoxazolinas substituídas, derivadas do metil-3-metóxi-2-(4-oxo-3,4-diidroftalazin-1-il)prop-2-enoato foram estudadas e sintetizadas a partir do metil-(4-oxo-3,4-diidroftalazin-1-il)acetato, o qual foi preparado a partir do anidrido ftálico. As estruturas dos novos compostos sintetizados foram caracterizadas por dados espectrais e suas atividades antimicrobianas e citotóxicas estudadas. Vários desses compostos mostraram boa atividade antimicrobiana.A series of some new 3-isoxazoline substituted methyl-3-methoxy-2-(4-oxo-3,4-dihydrophthalazin-1-yl)prop-2-enoate derivatives were designed and synthesized from methyl-(4-oxo-3,4-dihydrophthalazin-1-yl)acetate, which in turn was prepared from phthalic anhydride. The structures of synthesized new compounds were characterized by spectral data and studied for their antimicrobial activities and cytotoxicity. Several of these compounds showed good antimicrobial activity.Keywords: phthalazin-1(2H)-one, β-methoxyacrylate, strobilurins, isoxazoline IntroductionNitrogen-containing heterocyclic molecules constitute the largest portion of chemical entities, which are part of many natural products, fine chemicals, and biologically active pharmaceuticals. Strobilurins and their analogues constitute a large group of compounds that represent a new class of plant-protecting agents 1 that meet all the demands that are made nowadays for pesticides. They exhibit efficacy against a broad-spectrum of fungal diseases, possess significant post-infective activity, and have a unique mode of action. 2 Intensive studies aimed at a search for novel biologically active methoxyacrylate fungicides are currently under way by different manufacturers. 3 Studies on the structure of natural methoxyacrylates have made possible to create a novel class of synthetic fungicides with enhanced stability, high activity, and a broad spectrum of action. β-Methoxyacrylate which is a critical and common structural element of strobilurins, fund use in agrochemical agents, 4 antivirals, 5 antimalarials, 6 and fungicides. 7 There has been extensive industrial development of these compounds and their analogues. 8,9 In finding new β-methoxyacrylate derivatives, we observed that, phthalazines attached to these pharmacophore were not studied. Phthalazin-1(2H)-one derivatives are of considerable interest due to their antidiabetic, 10 antiallergic, 11 vasorelaxant, 12 PDE4 inhibitor, 13 VEGF (vascular endothelial growth factor) receptor tyrosine kinase (for the treatment of cancer), 14 The diverse biological activities of β-methoxyacrylate, phthalazin-1(2H)-one, and isoxazoline pharmacophores envisaged us to plan a new lead compounds that may exhibit wide pharmacological activities. By combining these pharmacophore components in a molecule to give a compact system, we designed and synthesized a series of phthalazin-1(2H)-one derivatives containing β-methoxyacrylate and isoxazoline moieties. Figure 1 reveals a framework of these three important biological active pharmacophore component systems.The synth...

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“…In fact, much attention has been paid to the synthesis of heterocyclic compounds bearing nitrogen and oxygen containing ring system dihydroisoxazoles (also named isoxazolines) are of great interest because they have proven potential pharmaceutical leads [16,17] and versatile intermediates for the synthesis of different classes of functionalized molecules and a variety of bioactive compounds [18]. They are associated with diverse pharmacological activities such as human influenza A virus [19], antituberculosis [20], antimicrobial [21,22] antidepressant [23], antimuscarinic [24], anti-inflammatory [25] and herbicidal effects [26].…”

Section: Introductionmentioning

confidence: 99%

Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene

et al. 2015

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We report herein the convenient procedures for the efficient and easy synthesis, and the antimicrobial and the anti-acetylcholinesterase evaluation of two new series of (R)-limonene derivatives. A substantial modification aimed at targeting to discover novel structures with a better antimicrobial and anti-acetylcholinesterase (anti-AChE) activities. The condensation of (R)-limonene (1) with various arylnitrile oxides led, via the 1,3-dipolar cycloaddition reaction, conducted with complete region-specificity, to a series of new limonene-dihydroisoxazoles, 2a-h. On the other hand, N-alkylation of the previously prepared limonene-lactam derivative (3) yielded the corresponding dipolarophile (4), which affords by condensation with arylnitrile oxides the expected new dihydroisoxazoles, 5a-h. The target compounds were completely characterized by 1 H NMR, 13 C NMR and MS. All the synthesized heterocyclic compounds were tested for their antimicrobial and anti-acetylcholinesterase activities. The dihydroisoxazoles 2a (IZ = 13.25 mm, cc = 1 mg/mL) and 5b (IZ = 13.75 mm, cc = 1 mg/mL) exhibited the highest antifungal activity. The greatest anti-acetylcolinesterase activity was exhibited by 2f (IC50 = 82±3 µg/mL) and by 5a (IC50 = 99±1 µg/mL).

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Anti-influenza Virus Activities of 2-Alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides

Cited by 41 publications

References 11 publications

One-pot synthesis of new series 3,4,5-trisubstituted–dihydroisoxazoline derivatives via 1,3-dipolar cycloaddition of nitrile oxides with chalcones

One-pot synthesis of new series 3,4,5-trisubstituted–dihydroisoxazoline derivatives via 1,3-dipolar cycloaddition of nitrile oxides with chalcones

Synthesis, antimicrobial and cytotoxicity studies of some novel modified Strobilurin derivatives

Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene

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