Isoxazole Chemistry Since 1963

Wakefield, B. J.; Wright, David J.

doi:10.1016/s0065-2725(08)60692-3

Cited by 78 publications

(25 citation statements)

References 230 publications

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“…The isoxazole moiety plays a pivotal role in our working hypothesis 38. It is a rigid linker, pre-organizing the anthracene and peptide in three dimensions, and potentially can also function as a prodrug to deliver the bioconjugate molecule to the cellular DNA.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis and biological evaluation of a novel class of anticancer agents: Anthracenylisoxazole lexitropsin conjugates

Han

Mosher

et al. 2009

Bioorganic & Medicinal Chemistry

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The synthesis and in vitro anti-tumor 60 cell lines screen of a novel series of anthracenyl isoxazole amides (AIMs)¥ (22-33) is described. The molecules consist of an isoxazole that pre-organizes a planar aromatic moiety and a simple amide and/or lexitropsin-oligopeptide. The new conjugate molecules were prepared via doubly activated amidation modification of Weinreb's amide formation technique, using SmCl 3 as an activating agent which produces improved yields for sterically hindered 3-aryl-4-isoxazolecarboxylic esters. The results of the National Cancer Institute's (NCI) 60 cell line screening assay show a distinct structure activity relationship (SAR), wherein a trend of the highest activity for molecules with one N-methylpyrrole peptide. Evidence consistent with a mechanism of action via the interaction of these compounds with G-quadruplex (G4) DNA, and a structural based rational for the observed selectivity of the AIMs for G4 over B-DNA is presented.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis and biological evaluation of a novel class of anticancer agents: Anthracenylisoxazole lexitropsin conjugates

Han

Mosher

et al. 2009

Bioorganic & Medicinal Chemistry

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“…Among heterocycles, the isoxazole unit constitutes an easily accessible nucleus that is present in a number of natural and pharmacological compounds [22], display a wide range of organic reactivities and used as an effective means of preparing new molecular scaffolds [23]. Isoxazoles have been repeatedly shown as useful synthons in organic synthesis [24].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterisation and Biological Screening of s-Triazine Based Chalcones and its Derivatization into Phenyl Pyrazolines, Isoxazoles

Solankee¹,

Tailor²

2015

ILCPA

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Heterocyclic derivatives such as phenyl pyrazolines and isoxaxoles were prepared from striazine based chalcones. Chalcones (A 1 -A 5 ) are synthesised by the reaction of compound (V) with various aromatic aldehydes. Moreover, further reaction of chalcones with phenyl hydrazine hydrochloride and hydroxylamine hydrochloride in the presence of alkali gives phenyl pyrazolines (A 6 -A 10 ) and isoxazoles (A 11 -A 15 ) derivatives respectively. The structures of the newly synthesised compounds were confiremed by spectroscopic (IR, 1 H NMR, 13 C NMR) and elemental analysis. All the newly synthesised compounds have been screened for their antimicrobial activity against selected Gram -positive (S. aureus and S. pyogenus), Gram -negative (E. coli and P. aeruginosa) bacterial and fungal strains (C. albicans, A. niger and A. clavatus).

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“…The isoxazolium methansulfate intermediates 7a and 7e were then converted to the respective tetrafluroborates [28] according to the reaction of Scheme 2. Previously 13 C-nmr studies were used to distinguish between isoxazole isomers [29,30]. Moreover, 1 H-nmr was used to compare the electronic effects of the substituents based on evaluation of their Hammett σ-constant parameters [31].…”

Section: Introductionmentioning

confidence: 99%

“…The preparation of these compounds can be envisaged using the so-called [3+2] atom fragments synthetic route, subtype CCC+NO [12][13][14], by condensation of an appropriate β-dicarbonyl intermediate (3) with hydroxylamine hydrochloride followed by alkaline hydrolysis (Figure 2). At this stage it was important to study the isoxazole-carboxylic acid moiety in order to establish the correct structure before further synthesis.…”

Section: Introductionmentioning

confidence: 99%

Structural investigation of 3,5‐disubstituted isoxazoles by ¹H‐nuclear magnetic resonance

Sechi¹,

Sannia²,

Orecchioni³

et al. 2003

Journal of Heterocyclic Chem

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This work is dedicated to the memory of Prof. Paolo Sanna HIV-1 integrase (IN) is a very promising and validated target for the development of therapeutic agents against AIDS. In an effort to design and synthesize biological isosteric analogs of β-diketoacid-containing inhibitors of IN, we prepared a series of substituted isoxazole carboxylic acids. Several of these compounds inhibited catalytic activities of purified IN at micromolar concentration range. With an aim to prepare a large number of analogues based on the isoxazole pharmacophore we focused our study on a series of 3,5-disubstituted isoxazole isomers. For a rapid structural analysis we discovered a convenient 1 H-nmr method for distinguishing between isomeric structures based on their H-4 assignments. This "finger print" approach to isomer identification will be useful in combinatorial chemistry settings where a mixture can be further derivatized.

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Isoxazole Chemistry Since 1963

Cited by 78 publications

References 230 publications

Design, synthesis and biological evaluation of a novel class of anticancer agents: Anthracenylisoxazole lexitropsin conjugates

Design, synthesis and biological evaluation of a novel class of anticancer agents: Anthracenylisoxazole lexitropsin conjugates

Synthesis, Characterisation and Biological Screening of s-Triazine Based Chalcones and its Derivatization into Phenyl Pyrazolines, Isoxazoles

Structural investigation of 3,5‐disubstituted isoxazoles by ¹H‐nuclear magnetic resonance

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Isoxazole Chemistry Since 1963

Cited by 78 publications

References 230 publications

Design, synthesis and biological evaluation of a novel class of anticancer agents: Anthracenylisoxazole lexitropsin conjugates

Design, synthesis and biological evaluation of a novel class of anticancer agents: Anthracenylisoxazole lexitropsin conjugates

Synthesis, Characterisation and Biological Screening of s-Triazine Based Chalcones and its Derivatization into Phenyl Pyrazolines, Isoxazoles

Structural investigation of 3,5‐disubstituted isoxazoles by 1H‐nuclear magnetic resonance

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Structural investigation of 3,5‐disubstituted isoxazoles by ¹H‐nuclear magnetic resonance