Structural Requirement of Isoflavonones for the Inhibitory Activity of Interleukin‐5.

Jung, Sang‐Hun; Cho, Soohyun; Lee, Jee‐Hyun; Ju, Jung-Hun; Kim, Mi‐Kyung; Lee, Seungho; Ryu, Jae‐Chun; Kim, Youngsoo

doi:10.1002/chin.200339224

Cited by 4 publications

(6 citation statements)

References 1 publication

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“…The reaction mixture was heated to reflux overnight under a N 2 atmosphere, then cooled and filtered. 31 The filtrate was concentrated under reduced pressure, and the residue was redissolved in ethyl acetate and washed with H 2 O (50 mL). The water layer was washed three times with ethyl acetate.…”

Section: E ) -1 -( 2 -( B E N Z Y L O X Y ) -6 -H Y D R O X Y P H E N...mentioning

confidence: 99%

Development of Flavonoid-Based Inverse Agonists of the Key Signaling Receptor US28 of Human Cytomegalovirus

et al. 2013

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A series of 31 chalcone- and flavonoid-based derivatives were synthesized in good overall yields and screened for their inverse agonist activity on the US28 receptor of human cytomegalovirus (HCMV). With one exception (e.g., 2-(5-bromo-2-methoxyphenyl)-3-hydroxy-4H-chromen-4-one), halogen-substituted flavonoids were typically more potent inverse agonists than their related hydro derivatives. While toxicity could be used to partially explain the inverse agonist activity of some members of the series, 5-(benzyloxy)-2-(5-bromo-2-methoxyphenyl)-4H-chromen-4-one (11b) acted on the US28 receptor as a nontoxic, inverse agonist. The full inverse agonism (efficacy, -89%) and potency (EC50 = 3.5 μM) observed with flavonoid 11b is especially important as it provides both a new tool to study US28 signaling and a potential platform for the future development of HCMV-targeting drugs.

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Section: E ) -1 -( 2 -( B E N Z Y L O X Y ) -6 -H Y D R O X Y P H E N...mentioning

confidence: 99%

Development of Flavonoid-Based Inverse Agonists of the Key Signaling Receptor US28 of Human Cytomegalovirus

et al. 2013

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“…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. The strong electron donating groups in the para-position of ring B led to isoflavones, the weak electron donating group to a mixture of both aurones and isoflavones, and the electron withdrawing groups ended with aurones (19).…”

Section: Methodsmentioning

confidence: 91%

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 correlation is not exceedingly sharp. In terms of r 2 , we found it necessary to omit two data points (12,13). Compound 12 is the only NHMe derivative whereas compound 13 presents the lowest B 5 value.…”

Section: Carboxylic Acid Bioisosteres Acylsulfonamides Acylsulfamidementioning

confidence: 98%

“…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%

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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Structural Requirement of Isoflavonones for the Inhibitory Activity of Interleukin‐5.

Cited by 4 publications

References 1 publication

Development of Flavonoid-Based Inverse Agonists of the Key Signaling Receptor US28 of Human Cytomegalovirus

Development of Flavonoid-Based Inverse Agonists of the Key Signaling Receptor US28 of Human Cytomegalovirus

Aurones: Interesting Natural and Synthetic Compounds with Emerging Biological Potential

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

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