Effects of the aryl linker and the aromatic substituent on the anti-HCV activities of aryl diketoacid (ADK) analogues

Kim, Jin‐Young; Kim, Ki-Sun; Lee, Hyo Seon; Park, Kwang‐Su; Park, Sun Young; Kang, Seock-Yong; Lee, Soo Jae; Park, Hyung Soon; Kim, Dong-Eun; Chong, Youhoon

doi:10.1016/j.bmcl.2008.07.008

Cited by 15 publications

(4 citation statements)

References 14 publications

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“…32,46 (1-(4-(Benzyloxy)phenyl)ethanone) derivatives 2a–e were synthesized through the benzylation of 4-hydroxyacetophenone using different benzyl halide derivatives and in the presence of anhydrous potassium carbonate as reported. 47–51 The synthesized intermediate ( 1 ) was reacted with either different substituted acetophenones, with intermediates 2a–e , or finally with thiazolidine-2,4-dione to bring out the targeted compounds 3a–h , 4a–e , and 5 respectively through Claisen–Schmidt condensation reactions. 52 As previously reported, chalcones could exist as trans or cis isomers.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of novel chloropyridazine hybrids as promising anticancer agents acting by apoptosis induction and PARP-1 inhibition through a molecular hybridization strategy

Abdelrahman,

Al-Karmalawy,

Jaballah

et al. 2024

RSC Med. Chem.

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Section: Resultsmentioning

confidence: 99%

Design and synthesis of novel chloropyridazine hybrids as promising anticancer agents acting by apoptosis induction and PARP-1 inhibition through a molecular hybridization strategy

Abdelrahman,

Al-Karmalawy,

Jaballah

et al. 2024

RSC Med. Chem.

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“…Also, in line with the substituted quercetins, the arylmethyloxy substituent (dotted box in 3, Fig. 1) increased the antiviral activity of the ADKs and the substituted ADKs showed potent inhibition of the RNA-dependent RNA polymerase (RdRp) of hepatitis C virus (HCV) (Kim et al, 2008) as well as the SCV NTPase/helicase (Lee et al, 2009b).…”

Section: Introductionmentioning

confidence: 83%

Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV)

et al. 2012

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Aryl diketoacid (ADK) is well known for antiviral activity which can be enhanced by introduction of an aromatic arylmethyl substituent. A natural flavonoid quercetin has a 3,5-dihydroxychromone pharmacophore which is in bioisosteric relationship with the 1,3-diketoacid moiety of the ADK. Thus, it was of our interest to test the antiviral activity of the quercetin derivatives with an arylmethyl group attached. In this study, we prepared a series of the 7-O-arylmethylquercetin derivatives with various aromatic substituents and evaluated their antiviral activity against the SARS-associated coronavirus (SARS-CoV, SCV) as well as hepatitis C virus (HCV). Single difference in the aromatic substituent fine-tuned the biological activity of the 7-O-arylmethylquercetin derivatives to result in two different classes of derivatives selectively active against SCV and HCV.

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“…With this information in hand, we designed several novel ADK analogues which showed good to excellent anti‐HCV activities (Figure 3) (10).…”

Section: Methodsmentioning

confidence: 99%

Identification of Novel HCV RNA‐dependent RNA polymerase Inhibitors Using Pharmacophore‐Guided Virtual Screening

Kim

et al. 2008

Chem Biol Drug Des

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We performed pharmacophore-guided virtual screening experiments using FlexX-Pharm to identify novel inhibitors of hepatitis C virus RNA-dependent RNA polymerase. Pharmacophore model generated from our previous analysis of the binding modes as well as structure-based three-dimensional quantitative structure-activity relationship studies of aryl diketoacid analogues was used. In pharmacophore-guided virtual screening study, among 37 447 compounds in LeadQuest chemical library, 40 compounds were selected as novel candidates of hepatitis C virus RNA-dependent RNA polymerase inhibitors, and their biological activities were evaluated. Especially, T29 was chosen for further development.

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Effects of the aryl linker and the aromatic substituent on the anti-HCV activities of aryl diketoacid (ADK) analogues

Cited by 15 publications

References 14 publications

Design and synthesis of novel chloropyridazine hybrids as promising anticancer agents acting by apoptosis induction and PARP-1 inhibition through a molecular hybridization strategy

Design and synthesis of novel chloropyridazine hybrids as promising anticancer agents acting by apoptosis induction and PARP-1 inhibition through a molecular hybridization strategy

Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV)

Identification of Novel HCV RNA‐dependent RNA polymerase Inhibitors Using Pharmacophore‐Guided Virtual Screening

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