Corrigendum to “Discovery of 3-acetyl-4-hydroxy-2-pyranone derivatives and their difluoridoborate complexes as a novel class of HIV-1 integrase inhibitors” [Bioorg. Med. Chem. 16 (2008) 8988–8998]

Ramkumar, Kavya; Tambov, K. V.; Gundla, Rambabu; Manaev, A. V.; Yarovenko, V. N.; Traven, V. F.; Neamati, Nouri

doi:10.1016/j.bmc.2008.08.082

Cited by 3 publications

(3 citation statements)

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“…Conversion of endo-cyclic tautomers A, B into the exo-cyclic ones C, D transforms the enone system of the side chain into the diene moiety which makes the Michael reaction at this fragment problematic. As in the case of the precursors 1-5, cyclic β-tricarbonyl system of the compounds 6-10 exists in solution in the enol form (B or D), which is confirmed by their NMR spectra and literature data [17,22,28,34]. However, under the described conditions nitromethane reacted with compounds 6-10 according to the scheme of 1,4-conjugate addition to the enone fragment of cinnamoyl moiety to give nitromethyl derivatives 11-15 in 47-92% yield ( Table 2).…”

supporting

confidence: 72%

Reaction of Nitromethane with Cinnamoyl Derivatives of Cyclic β-dicarbonyl Compounds. Application to the Synthesis of 2(3)-(4-aryl-pyrrolidin-2-ylidene)-1,3(2,4)-diones*

Pashkovsky

Dontsu

Rubinov

et al. 2014

Chem Heterocycl Comp

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The cyclic β-tricarbonyl functionality is an essential structural unit of a great diversity of natural products. Components of extracts from different plants (leptospermone, humulones, hulupones, filicines, etc.), various fungal metabolites and antibiotics (chelocardin, dutomicin, usnic acid), pheromones, and the kairomones of some Lepidoptera species, as well as many others, are cyclic β-triketones [1-3]. Many of these bioactive compounds exhibit a broad spectrum of useful therapeutic properties and are applied in traditional as well as in modern medicine. Synthetic benzoyl triketones based on the leptospermone structure template are currently used as effective agrochemicals (mesotrione, sulcotrione, tembotrione) and therapeutic agents for the treatment of hereditary tyrosinaemia type I disease (nitisinone, also known as NTBC) [4,5]. Moreover, carbo-, as well as heterocyclic β-tricarbonyl compounds, are valuable multifunctional precursors for the synthesis of natural products and biologically active heterocycles [2, 6-8].Among cyclic β-tricarbonyls, the compounds in which the keto function of the cinnamoyl substituent is involved in the β-tricarbonyl fragment are of special interest. Naturally occurring cinnamoyl derivatives of five-(linderone, lucidone [9], coruscanone B [10]) and six-membered cyclic β-dicarbonyl compounds (champanones [11], schefflerichalcone [12], saffloquinosides [13], and others) along with their synthetic congeners [14-17],

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supporting

confidence: 72%

Reaction of Nitromethane with Cinnamoyl Derivatives of Cyclic β-dicarbonyl Compounds. Application to the Synthesis of 2(3)-(4-aryl-pyrrolidin-2-ylidene)-1,3(2,4)-diones*

Pashkovsky

Dontsu

Rubinov

et al. 2014

Chem Heterocycl Comp

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“…L5 was used in synthesis of substituted 1,4-thiazepine and its analogs, applied to induce potential cell death in a variety of clinical conditions of uncontrolled or abnormal growth of cells [27]. Ramkumar et al used L1 and L5 to prepare the compounds that show a potential HIV-1 integrate inhibitory effect [28]. L1-L5 were also used for synthesis of 1,5-benzothiazepine derivatives [29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Vibrational spectroscopic study of dehydroacetic acid and its cinnamoyl pyrone derivatives

Billes

Elečková

Mikosch

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…They were also used as I type collagen gene transcription suppressing agents [6]. Difluoroborate complexes of 3-cinnamoyl 4-hydroxy-2-pyranone are known as a novel class of HIV-1 integrase inhibitors [7]. Moreover, cinnamoyl pyrones can be used for a synthesis of many heterocyclic compounds [8], particularly for the production of thiazepines, which are apoptosis inducers [9].…”

Section: Introductionmentioning

confidence: 99%

Structure and spectal properties of cinnamoyl pyrones and their vinylogs

Tykhanov¹,

Serikova²,

Yaremenko³

et al. 2010

Open Chemistry

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Abstract:The 1 H-NMR and quantum chemical analysis of the stability of tautomers of cinnamoyl pyrone derivatives and vinylogs has been studied. The relationship between the structure of the most stable tautomer and its spectral properties has been investigated. It has been determined that the tautomer of highest stability (88-100 molar %) has an α-pyrone structure and exhibits a trans-conformation in the cinnamoyl fragment. An intense fluorescence of dyes has been observed in non-polar solvents with cinnamoyl fragments having electron-donating substituents or several double bonds in the polymethine chain. A gradient in solvent polarity resulted in fluorescence quenching which permits the use of the dyes as intensometric fluorometric probes for medium polarity examination. Sp. z o.o. © Versita

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Corrigendum to “Discovery of 3-acetyl-4-hydroxy-2-pyranone derivatives and their difluoridoborate complexes as a novel class of HIV-1 integrase inhibitors” [Bioorg. Med. Chem. 16 (2008) 8988–8998]

Cited by 3 publications

References 0 publications

Reaction of Nitromethane with Cinnamoyl Derivatives of Cyclic β-dicarbonyl Compounds. Application to the Synthesis of 2(3)-(4-aryl-pyrrolidin-2-ylidene)-1,3(2,4)-diones*

Reaction of Nitromethane with Cinnamoyl Derivatives of Cyclic β-dicarbonyl Compounds. Application to the Synthesis of 2(3)-(4-aryl-pyrrolidin-2-ylidene)-1,3(2,4)-diones*

Vibrational spectroscopic study of dehydroacetic acid and its cinnamoyl pyrone derivatives

Structure and spectal properties of cinnamoyl pyrones and their vinylogs

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