Synthesis and Activity of a New Series of(Z)-3-Phenyl-2-benzoylpropenoic Acid Derivatives as Aldose Reductase Inhibitors

Wang, Shao-Jie; Yan, Jin; Hao, Dong; Niu, Xin-Wen; Cheng, Maosheng

doi:10.3390/12040885

Cited by 13 publications

(9 citation statements)

References 16 publications

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“…Moreover, compound 4 was converted into the first described α‐CF 3 ‐chalcone27 12 by utilizing methyl fluorosulfonyldifluoroacetate (MFSDA) in the presence of CuI 28. Acid 14 was formed from ester 13 upon saponification with aqueous NaOH at ambient temperature 18. The yellow chalcones were purified to obtain the pure isomers where the B‐ring and the X group are on the same side of the double bond, except for compounds 11 – 14 , which gave the other double‐bond isomers (Figure 2 and Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…[28] Acid 14 was formed from ester 13 upon saponification with aqueous NaOH at ambient temperature. [18] The yellow chalcones were purified to obtain the pure isomers where the B-ring and the X group are on the same side of the double bond, except for compounds 11-14, which gave the other double-bond isomers ( Figure 2 and Scheme 1).…”

Section: Synthesis Of A-x-chalconesmentioning

confidence: 99%

“…Modifications on the α‐position of the α,β‐unsaturated carbonyl unit have been achieved in synthetic triterpenoids,8 mimetics of those,9 cyclohexenones,10 chalcones,11 and our 3 (2 H )‐furanones 12. For the chalcones some examples of α‐X‐derivatives exist with X=halogen,13 nitro,11, 14 aromatic,15 alkyl,13a, c, 16 COOEt,13b, 17 COOH,18 CN,13b, c and alkoxy,16b but there is no study which reveals the potential influence of the different α‐X‐substituents on the reactivity towards thiols. Particularly, there is no scaffold on which a fine‐tuning of reactivity could be quantified experimentally and clearly related to a direct effect in a biological setting.…”

Section: Introductionmentioning

confidence: 99%

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Opening or Closing the Lock? When Reactivity Is the Key to Biological Activity

Al-Rifai

Rücker

Amslinger

2013

Chemistry A European J

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Thiol-mediated processes play a key role to induce or inhibit inflammation proteins. Tailoring the reactivity of electrophiles can enhance the selectivity to address only certain surface cysteines. Fourteen 2',3,4,4'-tetramethoxychalcones with different α-X substituents (X=H, F, Cl, Br, I, CN, Me, p-NO2-C6H4, Ph, p-OMe-C6H4, NO2, CF3, COOEt, COOH) were synthesized, containing the potentially electrophilic α,β-unsaturated carbonyl unit. The assessment of their reactivity as electrophiles in thia-Michael additions with cysteamine shows a change in the reactivity of more than six orders of magnitude. Moreover, a clear correlation between their reactivity and an influence on the inflammation proteins heme oxygenase-1 (HO-1) and the inducible NO synthase (iNOS) is demonstrated. As the biologically most active compound, the α-CF3 -chalcone is shown to inhibit the NO production in RAW264.7 mouse macrophages in the nanomolar range.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of A-x-chalconesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Opening or Closing the Lock? When Reactivity Is the Key to Biological Activity

Al-Rifai

Rücker

Amslinger

2013

Chemistry A European J

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“…Their chemical structures are summarized in Table 1. The procedures used to synthesize these compounds were described previously (15).…”

Section: Methodsmentioning

confidence: 99%

Chalcone Derivatives Inhibit Glutathione S‐Transferase P1‐1 Activity: Insights into the Interaction Mode of α, β‐Unsaturated Carbonyl Compounds

Wang¹,

Wang²,

Song³

et al. 2009

Chem Biol Drug Des

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Resistance to chemotherapeutic drugs has long been a considerable barrier to successful treatment of many cancers and over-expression of glutathione S-transferase P1-1 is correlated to carcinogenesis and resistance of cancer cells against chemotherapeutic agents. This study throws light on the role of chalcone derivatives, a new class of glutathione S-transferase P1-1 inhibitors potentially to overcome glutathione S-transferase P1-1-mediated chemotherapy resistance. Nineteen alpha-substituted chalcone derivatives were synthesized and their in vitro inhibitory effects on glutathione S-transferase P1-1 were determined. We interestingly found that most of these compounds showed inhibitory effect on glutathione S-transferase P1-1 activity. In addition, molecular field-based similarity analysis provides the necessary three-dimensional molecular field properties of alpha, beta-unsaturated carbonyl derivatives to inhibit glutathione S-transferase P1-1 activity. Thus, these compounds have great potential to be developed into novel chemotherapeutic sensitizers.

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“…www.chemmedchem.org tors for the treatment of diabetic complications, [36] as well as glutathione S-transferase P1-1 inhibitors, such as compound 11, which can play a role in overcoming resistance to chemotherapeutics. [37] These approaches show that Michael acceptor activity, together with binding affinity and substitution at the a-position of the a,b-unsaturated carbonyl system, leads to very promising activities.…”

mentioning

confidence: 99%

The Tunable Functionality of α,β‐Unsaturated Carbonyl Compounds Enables Their Differential Application in Biological Systems

Amslinger

2010

ChemMedChem

173

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alpha,beta-Unsaturated carbonyl compounds as potential drug candidates is a controversial topic since their potential Michael acceptor activity can lead to cell damage and cytotoxicity. Nevertheless, the alpha,beta-unsaturated carbonyl functionality can be employed as a tool to fine tune biological activity by directly manipulating this entity. Depending on their electronic properties, alpha,beta-unsaturated carbonyl functionalities display different reactivities, namely Michael addition, radical scavenging, oxidation or double bond isomerization. Modifying the alpha-position of the alpha,beta-unsaturated carbonyl system, a concept that has not been widely explored, could produce new, very interesting derivatives. Currently in drug development, irreversible binding in active sites has proven to be one answer to drug resistance in cancer treatment. Overall, natural products containing the alpha,beta-unsaturated carbonyl unit possess multiple biological activities that could be transferred into novel pharmaceutical agents.

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Synthesis and Activity of a New Series of(Z)-3-Phenyl-2-benzoylpropenoic Acid Derivatives as Aldose Reductase Inhibitors

Cited by 13 publications

References 16 publications

Opening or Closing the Lock? When Reactivity Is the Key to Biological Activity

Opening or Closing the Lock? When Reactivity Is the Key to Biological Activity

Chalcone Derivatives Inhibit Glutathione S‐Transferase P1‐1 Activity: Insights into the Interaction Mode of α, β‐Unsaturated Carbonyl Compounds

The Tunable Functionality of α,β‐Unsaturated Carbonyl Compounds Enables Their Differential Application in Biological Systems

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