The scope of thallium nitrate oxidative cyclization of chalcones; synthesis and evaluation of isoflavone and aurone analogs for their inhibitory activity against interleukin-5

Pillaiyar, Thanigaimalai; Yang, Hyun-Mo; Sharma, Vinay K.; Kim, Youngsoo; Jung, Sang‐Hun

doi:10.1016/j.bmc.2010.04.075

Cited by 14 publications

(9 citation statements)

References 26 publications

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“…No parameterization for substituent R 3 has been done. However, all the points fit well to the Equation (18). Compound 10 has the second lowest log1/IC 50 value within the dataset.…”

Section: Konstantinidou and D Hadjipavlou-litinamentioning

confidence: 74%

“…Although corticosteroids are established immunosuppressive agents, their action is not selective and they cause metabolic and endocrinal side effects [9], whereas compounds with IL-5 inhibitory activity act selectively in reducing eosinophilic inflammation. In the literature small molecules are referred as IL-5 inhibitors (Figure 1): chalcones [10,11], isothiazolones through modification of Cys66 (Cysteine66) in IL-5Ra (interleukin 5 receptor subunit alpha) [12], isoflavonones as sophoricoside analogues [13,14], hydroxyalkylaminomethylchromones [15], derivatives based on hydroxyethylaminomethyl-4H-chromen-4-one scaffold [16], chromone analogues [17], isoflavones and aurones [18]. Mepolizumab and reslizumab, two monoclonal anti-IL-5 antibodies, and benralizumab, a monoclonal antibody directed at the IL-5 receptor, have been tested in clinical trials for the treatment of bronchial asthma, nasal polyposis, atopic dermatitis, eosinophilic oesophagitis, hypereosinophilic syndrome and Churg-Strauss syndrome [19].…”

Section: Introductionmentioning

confidence: 99%

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Cytokines in terms of QSAR. Review, evaluation and comparative studies

Konstantinidou

Hadjipavlou‐Litina

2013

SAR and QSAR in Environmental Research

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Cytokines represent a class of chemical factors that act as mediators in the complex biological response of inflammation, potentially implicated in various diseases. Therefore, selective inhibition or antagonism of cytokines is a target of anti-inflammatory drug design. The QSAR (Quantitative Structure-Activity Relationships) analysis presented here attempts to identify the structural features and physicochemical properties that are significant for cytokine antagonists or inhibitors and in particular of i) interleukin-5 (IL-5), ii) interleukin-6 (IL-6) and iii) of the chemotactic cytokine (chemokine) interleukin-8 (IL-8). Firstly, a historical aspect of the limited published QSARs is discussed and then a 2D-QSAR analysis was carried out for 26 data sets of compounds using the C-QSAR program of Biobyte. In six cases hydrophobicity appeared to be important. Steric factors in the form of overall molar refractivity (CMR), molar refractivity of the substituent (MR), molar volume (MgVol), Taft's Es constant and the sterimol parameters B1 and B5 have a significant impact on biological activity in most of the derived equations whereas electronic parameters as σp, σm or Σσ appeared in five cases.

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“…No parameterization for substituent R 3 has been done. However, all the points fit well to the Equation (18). Compound 10 has the second lowest log1/IC 50 value within the dataset.…”

Section: Konstantinidou and D Hadjipavlou-litinamentioning

confidence: 74%

Section: Introductionmentioning

confidence: 99%

Cytokines in terms of QSAR. Review, evaluation and comparative studies

Konstantinidou

Hadjipavlou‐Litina

2013

SAR and QSAR in Environmental Research

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“…The following reductive elimination of Pd from the palladacycle leads to the desired aurone 47 in its (Z)-predominant isoform, while the resulting reduced Pd(0) is reoxidized by oxygen from air, thus maintaining the catalytic efficiency of the system (Scheme 7) Scheme 6. Cyclization of chalcones according to Thanigaimalai and Yang [59].…”

Section: Cyclization Of Chalconesmentioning

confidence: 99%

“…Additionally, Thanigaimalai and Yang pursued the cyclization of chalcones by exploiting thallium (III) nitrate in methanol solution followed by the addition of hydrochloric acid as the oxidant condition [ 59 ]. Using 1-(2-(cyclohexylmethoxy)-6-hydroxyphenyl)-3-phenylprop-2-en-1-one 41 as the starting material, they obtained either the aurone derivatives 42 or the isoflavone derivatives 43 depending on the substitution pattern on the B ring of the chalcone.…”

Section: Synthetic Strategies To Obtain Auronesmentioning

confidence: 99%

Aurones: A Golden Resource for Active Compounds

2021

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Deemed as poorly represented in nature, aurones have been often overlooked by researchers compared to other members of the flavonoid superfamily. However, over the past two decades, they have been reassessed by the scientific community, who are increasingly appreciating their ability to modulate several biological pathways. This review summarizes the recent literature on this class of compounds, which has been analyzed from both a chemical and a functional point of view. Original articles, reviews and editorials featured in Pubmed and Scifinder over the last twenty years have been taken into account to provide the readers with a view of the chemical strategies to obtain them, their functional properties, and their potential of technological use. The resulting comprehensive picture aims at raising the awareness of these natural derivatives as effective drug candidates, fostering the development of novel synthetic analogues.

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“…Filtration and recrystallization in EtOH yielded the desired aurones (17) [19]. Thanigaimalai and Yang described a synthetic route to aurones via oxidation of 2-hydroxy-6-cyclohexylmethoxychalcones with thallium (III) nitrate (Scheme 6) [20]. In continuation of their previous work [21,22] they treated different chalcones (18) with thallium (III) nitrate in methanol, first at room temperature for 24 h, and then heated to 65°C, followed by addition of hydrochloric acid in a one pot oxidative cyclisation to achieve the corresponding isoflavones (not shown) and/or aurones (19) depending on the electronic nature of substituents on ring B of the chalcones.…”

Section: Synthesis Of Aurone Derivativesmentioning

confidence: 99%

Aurones: Interesting Natural and Synthetic Compounds with Emerging Biological Potential

Zwergel¹,

Gaascht

Diederich

et al. 2012

Natural Product Communications

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Aurones [2-benzylidenebenzofuran-3(2H)-ones] are either natural or synthetic compounds, belonging to the flavonoid family. They are isomeric to flavones and provide a bright yellow color to the plants in which they occur. Today, a literature survey indicates that the related flavonoids have been studied not only for their physiological properties and effects on Nature, but also for their therapeutic potential. Aurones are recently attracting the interest of an increasing number of research groups, and, since the last review, some interesting advances have been made in understanding the aurones. In this review, we report the recent advances made on the synthetic routes towards aurones. We also highlight their activity in different biological areas, as well as applied genetic plant modifications to produce these colored compounds. Their synthesis, structure-activity relationships and the importance of the substitution pattern will also be mentioned. Finally, some aspects regarding the possible development of aurones will be discussed briefly.

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The scope of thallium nitrate oxidative cyclization of chalcones; synthesis and evaluation of isoflavone and aurone analogs for their inhibitory activity against interleukin-5

Cited by 14 publications

References 26 publications

Cytokines in terms of QSAR. Review, evaluation and comparative studies

Cytokines in terms of QSAR. Review, evaluation and comparative studies

Aurones: A Golden Resource for Active Compounds

Aurones: Interesting Natural and Synthetic Compounds with Emerging Biological Potential

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